Name: 2510-03-4|2-(3,4-Dihydronaphthalen-1(2H)-ylidene)malononitrile|95%
Brand: Ambeed
SKU: A197025
Price: 216.0 USD
Availability: InStock
Rating: 93 (22 reviews)

1
[ 529-34-0 ]
[ 109-77-3 ]
[ 2510-03-4 ]

Yield	Reaction Conditions	Operation in experiment
100%	With aluminum oxide Inert atmosphere; Neat (no solvent);
93%	With ammonium acetate; acetic acid In toluene for 10h; Reflux; Dean-Stark;
89%	With 1-butyl-3-methylimidazolium hydroxide at 25 - 30℃; for 0.666667h;

88%	With ammonium acetate; acetic acid In toluene Heating;
87%	With ammonium acetate; acetic acid In toluene for 6h; Dean-Stark; Reflux;	Synthesis of α,α-dicyanoolefins 2a-c In a 50 mL two-way flask were added toluene (30 mL), malonitrile (1.72 g, 26 mmol), α-tetralone (2.66 mL, 20 mmol), ammonium acetate (0.33 g, 4,28 mmol) and glacial acetic acid (2 mL). With the aid of a Dean-Stark apparatus for water removal, the reaction was refluxed for 6 hours. The solvent was then evaporated. 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile (2a): The product was obtained as a green solid after purification by washing with ice-cold ethanol in 87% yield (3.39 g, 17.45 mmol). 1H NMR (400 MHz, CDCl3) δ: 8.14 (dd, J = 8.0, 0.7 Hz, 1H), 7.43 (td, J = 7.5, 1.3 Hz, 1H), 7.32-7.25 (m, 1H), 7.24-7.19 (m, 1H), 3.04-2.91 (m, 2H), 2.82 (t, J = 6.3, 2H), 2.00-1.88 (m, 2H). 13C NMR (100 MHz, CDCl3) δ: 172.6; 142.0; 133.7; 130.0; 129.5; 128.0; 126.9; 114.0; 113.4; 79.8; 33.1; 29.7, 22.2.
76%	With ammonium acetate; acetic acid In toluene for 4h; Reflux; Dean-Stark; Inert atmosphere;
71%	With ammonium acetate; acetic acid In benzene at 130℃; Dean-Stark;
65%
45%	With ammonium acetate; acetic acid In toluene for 24h; Reflux;
42%	With ammonium acetate; acetic acid In toluene Reflux; Dean-Stark;
	With ammonium acetate; acetic acid; benzene unter Entfernen des entstehenden Wassers;
	With ammonium acetate; acetic acid
	With ammonium acetate; acetic acid In benzene for 24h; Heating;
	With ammonium acetate; acetic acid In benzene for 18h; Heating;
	With aluminum oxide
	With ammonium acetate; acetic acid In toluene Heating;
	With ammonium acetate; acetic acid In toluene Reflux;
	With [BmIm]OH In ethanol Reflux;
	Alkaline conditions; Inert atmosphere; Glovebox;
	With ammonium acetate; acetic acid In toluene for 24h; Reflux;
	With ammonium acetate; acetic acid In toluene Dean-Stark; Reflux;	1. General procedures for the preparation of vinyl malononitrile General procedure: In a 100 mL round-bottomflask wasplaced with 40 mL toluene containing ammonium acetate (1000 mg) and glacialacetic acid (3 mL). Then malononitrile (30 mmol) and the ketone (33 mmol) wereadded and the reaction was refluxed and stirred vigorously, the water formed inthe reaction was removed by a Dean and Stark trap placed under the refluxcondenser. After the completion of the reaction, the mixture was cooled toambient temperature and diluted with EtOAc, then washed with brine. The organicphase was dried over Na2SO4 and the solvent wasevaporated under reduced pressure. The residue was recrystallized from ethanolcrystallization or chromatography to give pure products.
	With ammonium acetate; acetic acid In toluene Reflux; Dean-Stark;
	With triethylamine In ethanol at 20℃; for 2h;	General procedure for synthesis of methylenemalononitriles General procedure: Malononitrile (9.5 mmol) and the aldehyde (9.5 mmol) were dissolved in 5 mL of EtOH in a 50 mL flask, followed by adding one drop of triethylamine. After stirring at room temperature for 2 h, filtrate the solid to give the crude products. Further purification was completed by flash chromatography.
	With ammonium acetate; acetic acid In toluene Reflux; Dean-Stark;
	With ammonium acetate; acetic acid In toluene at 110℃;	1 step 1: Compound 1-tetralone C1 (2.9 g, 20 mmol)And malononitrile (2.6 g, 40 mmol) was added to the reaction unit with a water separator.Toluene (10 ml) was added to the device as a solvent.Ammonium acetate (3.8 g, 50 mmol) was dissolved in acetic acid (5.5 ml, 100 mmol), added to the reaction apparatus, heated to reflux (110 ° C), and then cooled to room temperature after completion of the reaction.Extract with diethyl ether and dry the organic phase with Na2SO4.The crude compound S1 was obtained by spin-drying, and the next step was carried out without purification;
	With ammonium acetate In acetic acid Heating;

Reference： [1]Location in patent: experimental part Yang, Xianghua; Fox, Thomas; Berke, Heinz [Organic and Biomolecular Chemistry, 2012, vol. 10, # 4, p. 852 - 860]
[2]Pan, Hong; Han, Man-Yi; Li, Pinhua; Wang, Lei [Journal of Organic Chemistry, 2019, vol. 84, # 21, p. 14281 - 14290]
[3]Ranu, Brindaban C.; Jana, Ranjan [European Journal of Organic Chemistry, 2006, # 16, p. 3767 - 3770]
[4]Xue, Dong; Chen, Ying-Chun; Cui, Xin; Wang, Qi-Wei; Zhu, Jin; Deng, Jin-Gen [Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3584 - 3591]
[5]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]
[6]Broman, Soren Lindbaek; Kushnir, Oleg; Rosenberg, Martin; Kadziola, Anders; Daub, Joerg; Nielsen, Mogens Brondsted [European Journal of Organic Chemistry, 2015, vol. 2015, # 19, p. 4119 - 4130]
[7]Lahtigui, Ouidad; Emmetiere, Fabien; Zhang, Wei; Jirmo, Liban; Toledo-Roy, Samira; Hershberger, John C.; Macho, Jocelyn M.; Grenning, Alexander J. [Angewandte Chemie - International Edition, 2016, vol. 55, # 51, p. 15792 - 15796][Angew. Chem., 2016, vol. 128, # 51, p. 16024 - 16028]
[8]Elinson; Fedukovich; Vereshchagin; Dorofeev; Dmitriev; Nikishin [Russian Chemical Bulletin, 2003, vol. 52, # 10, p. 2235 - 2240]
[9]Chaouni, Wafaa; Aadil, Mina; Djellal, Ahmed; Kirsch, Gilbert [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2014, vol. 69, # 5, p. 509 - 518]
[10]Longstreet, Ashley R.; Campbell, Brian S.; Gupton, B. Frank; McQuade, D. Tyler [Organic Letters, 2013, vol. 15, # 20, p. 5298 - 5301]
[11]Mowry [Journal of the American Chemical Society, 1945, vol. 67, p. 1050]
[12]Hart,H.; Kim,Y.C. [Journal of Organic Chemistry, 1966, vol. 31, p. 2784 - 2789]
[13]Aadil, M.; Kirsch, G. [Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 82, # 1-4, p. 91 - 98]
[14]Dai, Yujia; Guo, Yan; Frey, Robin R.; Ji, Zhiqin; Curtin, Michael L.; Ahmed, Asma A.; Albert, Daniel H.; Arnold, Lee; Arries, Shannon S.; Barlozzari, Teresa; Bauch, Joy L.; Bouska, Jennifer J.; Bousquet, Peter F.; Cunha, George A.; Glaser, Keith B.; Guo, Jun; Li, Junling; Marcotte, Patrick A.; Marsh, Kennan C.; Moskey, Maria D.; Pease, Lori J.; Stewart, Kent D.; Stoll, Vincent S.; Tapang, Paul; Wishart, Neil; Davidsen, Steven K.; Michaelides, Michael R. [Journal of Medicinal Chemistry, 2005, vol. 48, # 19, p. 6066 - 6083]
[15]Poulsen, Thomas B.; Bell, Mark; Jrgensen, Karl Anker [Organic and Biomolecular Chemistry, 2006, vol. 4, # 1, p. 63 - 70]
[16]Lu, Jun; Liu, Feng; Zhou, Wei-Juan; Loh, Teck-Peng [Tetrahedron Letters, 2008, vol. 49, # 37, p. 5389 - 5392]
[17]Lu, Jun; Liu, Feng; Loh, Teck-Peng [Advanced Synthesis and Catalysis, 2008, vol. 350, # 11-12, p. 1781 - 1784]
[18]Location in patent: experimental part Chen, Zhiwei; Ding, Kai; Su, Weike [Synthetic Communications, 2011, vol. 41, # 10, p. 1410 - 1420]
[19]Cao, Ying; Zhang, Song-Chen; Zhang, Min; Shen, Guang-Bin; Zhu, Xiao-Qing [Journal of Organic Chemistry, 2013, vol. 78, # 14, p. 7154 - 7168]
[20]Orlikova, Barbora; Chaouni, Wafaa; Schumacher, Marc; Aadil, Mina; Diederich, Marc; Kirsch, Gilbert [European Journal of Medicinal Chemistry, 2014, vol. 85, p. 450 - 457]
[21]Zhou, Long-Hua; Wang, Na; Chen, Guan-Nan; Yang, Qi; Yang, Sheng-Yong; Zhang, Wei; Zhang, Yang; Yu, Xiao-Qi [Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 109, p. 170 - 177]
[22]Li, Xuanyi; Xu, Xiuyan; Wei, Weiwei; Lin, Aijun; Yao, Hequan [Organic Letters, 2016, vol. 18, # 3, p. 428 - 431]
[23]Liu, Yingtian; Dang, Xinxin; He, Yu; Bai, Hudong; Chen, Xuehong; Li, Jun-Long; Fan, Junting; Jiang, Hezhong; Li, Jiahong [Synthetic Communications, 2019, vol. 49, # 5, p. 662 - 671]
[24]Chen, Hui; Zhao, Sihan; Cheng, Shaobing; Dai, Xingjie; Xu, Xiaoying; Yuan, Weicheng; Zhang, Xiaomei [Journal of Heterocyclic Chemistry, 2019, vol. 56, # 5, p. 1672 - 1683]
[25]Current Patent Assignee: HENAN NORMAL UNIVERSITY - CN109761927, 2019, A Location in patent: Paragraph 0015
[26]Emmetiere, Fabien; Grenning, Alexander J. [Synthesis, 2020, vol. 52, # 2, p. 3077 - 3085]
[27]Wu, Hui-Chun; Wang, Chen; Chen, Ying-Han; Liu, Yan-Kai [Chemical Communications, 2021, vol. 57, # 14, p. 1762 - 1765]

2
[ 2510-03-4 ]
[ 33513-42-7 ]
[ 155413-17-5 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium fluoride; natural phosphate; trichlorophosphate at 70 - 80℃; for 3h;
62%	With trichlorophosphate at 20 - 80℃; for 3.5h;	General procedure for the synthesis of 2-chloro-3-cyanopyridines 4 General procedure: To a flask containing 10 mmol of a gem-dicyanoalkene 1 and 20 mmol (3.0 g) of POCl3 in DMF (10 mL), 0.1 g of phosphate catalyst (KF/NP) was added, and the mixture was stirred at room temperature for 30 min. Then the bath temperature was slowly raised to 70 - 80 °C. The reaction mixture was heated for 3 h and after cooling poured into cold water. The formed solid was filtered and recrystallized or purified by column chromatography.
	With trichlorophosphate at 80℃; for 3h;

With trichlorophosphate at 70 - 80℃; for 3h;

Reference： [1]Zahouily, Mohamed; Bahlaouan, Bouchaib; Abrouki, Younes; Salah, Mohamed; Bahlaouan, Ouafa; Rayadh, Ahmed; Aadil, Mina; Sebti, Said [Journal of Chemical Research, 2006, # 1, p. 34 - 36]
[2]Chaouni, Wafaa; Aadil, Mina; Djellal, Ahmed; Kirsch, Gilbert [Zeitschrift fur Naturforschung, B: Chemical Sciences, 2014, vol. 69, # 5, p. 509 - 518]
[3]Aadil, M.; Kirsch, G. [Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 82, # 1-4, p. 91 - 98]
[4]Orlikova, Barbora; Chaouni, Wafaa; Schumacher, Marc; Aadil, Mina; Diederich, Marc; Kirsch, Gilbert [European Journal of Medicinal Chemistry, 2014, vol. 85, p. 450 - 457]

3
[ 5153-67-3 ]
[ 2510-03-4 ]
[ 870086-17-2 ]

Yield	Reaction Conditions	Operation in experiment
84%	In acetone at -40℃; for 38h;
83%	With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea In toluene at 5℃; for 60h; enantioselective reaction;	II. General procedure for asymmetric vinylogous Michael addition of vinyl malononitriles to nitrostyrene General procedure: To a stirred solution of 4 (0.92 mg, 0.002mmol, 5 mol %) and vinyl malononitriles 1 (0.1mmol) in Toluene (1 mL), nitrostyrene 2 (0.12 mmol) was added. The solution was stirred atambient temperature for mentioned days. After the reaction was completed (monitored by TLC), the resulting mixture was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel to give the product 3.

Reference： [1]Poulsen, Thomas B.; Bell, Mark; Jrgensen, Karl Anker [Organic and Biomolecular Chemistry, 2006, vol. 4, # 1, p. 63 - 70]
[2]Vishwanath, Manjunatha; Prakash, Muthuraj; Vinayagam, Poopathy; Kesavan, Venkitasamy [Synthesis, 2016, vol. 48, # 16, p. 2671 - 2678]

4
[ 2510-03-4 ]
[ 177896-09-2 ]
(1R,2R)-[(1-dicyanomethylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-phenyl-methyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1-{(1R,2R)-2-(dimethylamino)cyclohexyl}-3-cyclohexylthiourea; 4 A molecular sieve In toluene at 20℃;

Reference： [1]Liu, Tian-Yu; Cui, Hai-Lei; Long, Jun; Li, Bang-Jing; Wu, Yong; Ding, Li-Sheng; Chen, Ying-Chun [Journal of the American Chemical Society, 2007, vol. 129, # 7, p. 1878 - 1879]

5
[ 2510-03-4 ]
[ 741259-87-0 ]
[(1-dicyanomethylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-(4-methoxy-phenyl)-methyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium phosphate In toluene at -25℃;

Reference： [1]Niess, Barbara; Jorgensen, Karl Anker [Chemical Communications, 2007, # 16, p. 1620 - 1622]

6
[ 2510-03-4 ]
tert-butyl (furan-2-yl(phenylsulfonyl)methyl)carbamate [ No CAS ]
[(1-dicyanomethylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-furan-2-yl-methyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium phosphate In toluene at -25℃;

Reference： [1]Niess, Barbara; Jorgensen, Karl Anker [Chemical Communications, 2007, # 16, p. 1620 - 1622]

7
[ 2510-03-4 ]
N-Boc-α-(phenylsulfonyl)-α-(thiophen-2-yl)methylamine [ No CAS ]
[(1-dicyanomethylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-thiophen-2-yl-methyl]-carbamic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium phosphate In toluene at -25℃;

Reference： [1]Niess, Barbara; Jorgensen, Karl Anker [Chemical Communications, 2007, # 16, p. 1620 - 1622]

8
[ 2510-03-4 ]
[ 762-42-5 ]
[ 109-77-3 ]
[ 1628848-04-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: dimethyl acetylenedicarboxylate; malononitrile With triethylamine In ethanol at 20℃; for 0.333333h; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In ethanol	Dialkyl 5-Amino-4,6,6-tricyano-1-(2-methoxy-2-oxoethyl)cyclohexa-2,4-diene-1-carboxylates (3); General Procedure General procedure: A mixture of malononitrile (1.0 mmol), dialkylacetylenedicarboxylate 2 (1.0 mmol), and Et3N (one drop) in EtOH (5 mL) was stirred at r.t. for 20 min. A solution of α,α-dicyanoolefin 1 (1.0 mmol) and Et3N (1 mmol) in EtOH (3 mL) was then added. When the reaction was complete, the solvent was removed under reduced pressure and the residue was purified by column chromatography [silica gel,hexane/EtOAc, (1:8)].

Reference： [1]Alizadeh, Abdolali; Sedighian, Hadi; Bayat, Fahimeh [Synlett, 2014, vol. 25, # 3, p. 389 - 392]

9
[ 2510-03-4 ]
[ 762-21-0 ]
[ 109-77-3 ]
[ 1628848-05-4 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: acetylenedicarboxylic acid diethyl ester; malononitrile With triethylamine In ethanol at 20℃; for 0.333333h; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In ethanol	Dialkyl 5-Amino-4,6,6-tricyano-1-(2-methoxy-2-oxoethyl)cyclohexa-2,4-diene-1-carboxylates (3); General Procedure General procedure: A mixture of malononitrile (1.0 mmol), dialkylacetylenedicarboxylate 2 (1.0 mmol), and Et3N (one drop) in EtOH (5 mL) was stirred at r.t. for 20 min. A solution of α,α-dicyanoolefin 1 (1.0 mmol) and Et3N (1 mmol) in EtOH (3 mL) was then added. When the reaction was complete, the solvent was removed under reduced pressure and the residue was purified by column chromatography [silica gel,hexane/EtOAc, (1:8)].

Reference： [1]Alizadeh, Abdolali; Sedighian, Hadi; Bayat, Fahimeh [Synlett, 2014, vol. 25, # 3, p. 389 - 392]

10
[ 2510-03-4 ]
[ 5147-80-8 ]
2-amino-11-imino-3b,4,5-11-tetrahydrobenzo[f]-pyrazolo[5,1-α]isoquinoline-3,10-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: To a solution of α,α-dicyanoolefin 1 (1 mmol) and ketenedithioacetal 2 (1 mmol) in EtOH (3 mL) was added Et3N (1mmol), and the solution was stirred for 30 min at r.t. Then,excess hydrazine was added to mixture. Upon completion(2 h, monitoring by TLC), the mixture was filtered and theprecipitate washed with EtOH (2 × 4 mL) to afford the pureproducts 3a,b,e,f and 4a-d.

Reference： [1]Synlett,2014,vol. 25,p. 2475 - 2479

11
[ 2510-03-4 ]
[ 762-42-5 ]
dimethyl 2-dicyano(1,2-dihydro-4-naphthalenyl)methyl-3-(1-dicyanomethylene-1,2,3,4-tetrahydro-2-naphthalenyl)succinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine In ethanol at 20℃; for 10h;	General procedure for the preparation of compounds 5a-d General procedure: To a mixture of 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile 4 (2mmol) and dialkyl acetylenedicarboxylate 2 (1mmol) in EtOH (5mL) was added triethylamine (6 drops). The mixture was stirred at room temperature. After completion, monitored by TLC, the mixture was filtered and the precipitate washed with ethanol (2×4mL) to afford the pure product 5a-d.

Reference： [1]Alizadeh, Abdolali; Hosseini, Seyed Yasub; Sedighian, Hadi; Bayat, Fahimeh; Zhu, Zhe; Dusek, Michal [Tetrahedron, 2015, vol. 71, # 41, p. 7885 - 7891]

12
[ 2510-03-4 ]
[ 762-21-0 ]
diethyl 2-dicyano(1,2-dihydro-4-naphthalenyl)methyl-3-(1-dicyanomethylene-1,2,3,4-tetrahydro-2-naphthalenyl)succinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In ethanol at 20℃; for 10h;	General procedure for the preparation of compounds 5a-d General procedure: To a mixture of 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile 4 (2mmol) and dialkyl acetylenedicarboxylate 2 (1mmol) in EtOH (5mL) was added triethylamine (6 drops). The mixture was stirred at room temperature. After completion, monitored by TLC, the mixture was filtered and the precipitate washed with ethanol (2×4mL) to afford the pure product 5a-d.

Reference： [1]Alizadeh, Abdolali; Hosseini, Seyed Yasub; Sedighian, Hadi; Bayat, Fahimeh; Zhu, Zhe; Dusek, Michal [Tetrahedron, 2015, vol. 71, # 41, p. 7885 - 7891]

13
[ 14447-03-1 ]
[ 2510-03-4 ]
diisopropyl 2-dicyano(1,2-dihydro-4-naphthalenyl)methyl-3-(1-dicyanomethylene-1,2,3,4-tetrahydro-2-naphthalenyl)succinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In ethanol at 20℃; for 10h;	General procedure for the preparation of compounds 5a-d General procedure: To a mixture of 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile 4 (2mmol) and dialkyl acetylenedicarboxylate 2 (1mmol) in EtOH (5mL) was added triethylamine (6 drops). The mixture was stirred at room temperature. After completion, monitored by TLC, the mixture was filtered and the precipitate washed with ethanol (2×4mL) to afford the pure product 5a-d.

Reference： [1]Alizadeh, Abdolali; Hosseini, Seyed Yasub; Sedighian, Hadi; Bayat, Fahimeh; Zhu, Zhe; Dusek, Michal [Tetrahedron, 2015, vol. 71, # 41, p. 7885 - 7891]

14
[ 2510-03-4 ]
[ 66086-33-7 ]
di(tert-butyl) 2-dicyano(1,2-dihydro-4-naphthalenyl)methyl-3-(1-dicyanomethylene-1,2,3,4-tetrahydro-2-naphthalenyl)succinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine In ethanol at 20℃; for 10h;	General procedure for the preparation of compounds 5a-d General procedure: To a mixture of 2-(3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile 4 (2mmol) and dialkyl acetylenedicarboxylate 2 (1mmol) in EtOH (5mL) was added triethylamine (6 drops). The mixture was stirred at room temperature. After completion, monitored by TLC, the mixture was filtered and the precipitate washed with ethanol (2×4mL) to afford the pure product 5a-d.

Reference： [1]Alizadeh, Abdolali; Hosseini, Seyed Yasub; Sedighian, Hadi; Bayat, Fahimeh; Zhu, Zhe; Dusek, Michal [Tetrahedron, 2015, vol. 71, # 41, p. 7885 - 7891]

15
[ 2510-03-4 ]
[ 31541-36-3 ]
C₂₉H₂₁N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With <i>L</i>-proline In ethanol; water at 20℃; for 4h; Green chemistry;	Experimental procedure for the synthesis of 6a-e General procedure: 3-(2-Oxo-2-phenylethylidene)indolin-2-one1 5 (1 mmol) and alkylidene malononitrile 3a-e (1 mmol) were stirred in a mixture of EtOH:H2O (2:1) in the presence of L-proline (15 mol%) at room temperature for 3 h. The solid precipitated out was filtered off and recrystallized from methanol to afford product 6a-e as a white solid.

Reference： [1]Kiruthika, Selvarangam E.; Perumal, Paramasivan T; Balachandran; Ignacimuthu [Journal of Chemical Sciences, 2014, vol. 126, # 1, p. 177 - 185]

16
[ 2510-03-4 ]
[ 399-25-7 ]
2-((S)-2-((R)-1-(2-fluorophenyl)-2-nitroethyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]
2-((R)-2-((S)-1-(2-fluorophenyl)-2-nitroethyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea; In toluene; at 5℃; for 60h;	General procedure: To a stirred solution of 4 (0.92 mg, 0.002mmol, 5 mol %) and vinyl malononitriles 1 (0.1mmol) in Toluene (1 mL), nitrostyrene 2 (0.12 mmol) was added. The solution was stirred atambient temperature for mentioned days. After the reaction was completed (monitored by TLC), the resulting mixture was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel to give the product 3.

Reference： [1]Synthesis,2016,vol. 48,p. 2671 - 2678

17
[ 2510-03-4 ]
1-chloro-2-(2-nitrovinyl)benzene [ No CAS ]
2-((S)-2-((R)-1-(2-chlorophenyl)-2-nitroethyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea In toluene at 5℃; for 60h; enantioselective reaction;	II. General procedure for asymmetric vinylogous Michael addition of vinyl malononitriles to nitrostyrene General procedure: To a stirred solution of 4 (0.92 mg, 0.002mmol, 5 mol %) and vinyl malononitriles 1 (0.1mmol) in Toluene (1 mL), nitrostyrene 2 (0.12 mmol) was added. The solution was stirred atambient temperature for mentioned days. After the reaction was completed (monitored by TLC), the resulting mixture was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel to give the product 3.

Reference： [1]Vishwanath, Manjunatha; Prakash, Muthuraj; Vinayagam, Poopathy; Kesavan, Venkitasamy [Synthesis, 2016, vol. 48, # 16, p. 2671 - 2678]

18
[ 2510-03-4 ]
[ 3156-37-4 ]
2-((S)-2-((R)-1-(4-bromophenyl)-2-nitroethyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-((S)-1-methylpyrrolidin-2-yl)(phenyl)methyl)thiourea In toluene at 5℃; for 60h; enantioselective reaction;	II. General procedure for asymmetric vinylogous Michael addition of vinyl malononitriles to nitrostyrene General procedure: To a stirred solution of 4 (0.92 mg, 0.002mmol, 5 mol %) and vinyl malononitriles 1 (0.1mmol) in Toluene (1 mL), nitrostyrene 2 (0.12 mmol) was added. The solution was stirred atambient temperature for mentioned days. After the reaction was completed (monitored by TLC), the resulting mixture was concentrated under reduced pressure and the residue was purified through column chromatography on silica gel to give the product 3.

Reference： [1]Vishwanath, Manjunatha; Prakash, Muthuraj; Vinayagam, Poopathy; Kesavan, Venkitasamy [Synthesis, 2016, vol. 48, # 16, p. 2671 - 2678]

19
[ 2510-03-4 ]
[ 228412-76-8 ]
6-amino-11-tosyl-2,13-dihydro-1H-naphtho[2,1-a]carbazole-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.
49%	With triethylamine In acetonitrile at 50℃; for 24h; Inert atmosphere;

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]
[2]Cao, Dongdong; Ying, Anguo; Mo, Hanjie; Chen, Dingben; Chen, Gang; Wang, Zhiming; Yang, Jianguo [Journal of Organic Chemistry, 2018, vol. 83, # 20, p. 12568 - 12574]

20
[ 2510-03-4 ]
C₁₃H₁₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With formic acid; palladium diacetate at 20℃; for 7h;	General procedure for synthesis of monoamides 2 General procedure: A mixture of 2-substituted methylenemalononitrile (0.325 mmol) and Pd(OAc)2 (1.82mg, 2.5 mol%) in HCOOH (2.0 mL) was stirred at room temperature for 10 min and then diluted with water. The mixture was saturated with sodium carbonate until the pH=7-8, followed by extraction with dichloromethane (3*20 mL). The combined organic phase was washed with saturated brine (320 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, petroleum ether:ethyl acetate = 2:1) to give (E)- Monoamides.

Reference： [1]Liu, Yingtian; Dang, Xinxin; He, Yu; Bai, Hudong; Chen, Xuehong; Li, Jun-Long; Fan, Junting; Jiang, Hezhong; Li, Jiahong [Synthetic Communications, 2019, vol. 49, # 5, p. 662 - 671]

21
[ 2510-03-4 ]
[ 2960-55-6 ]
2-((S)-2-((R)-1-(4-nitrophenyl)-3-oxo-3-phenylpropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	7 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

22
[ 2510-03-4 ]
[ 22966-11-6 ]
2-((S)-2-((R)-1-(2-chlorophenyl)-3-oxo-3-phenylpropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: (2E)-3-(2-chlorophenyl)-1-phenylprop-2-en-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	9 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

23
(E)-3-(4-chlorophenyl)-1-(4-iodophenyl)prop-2-en-1-one [ No CAS ]
[ 2510-03-4 ]
2-((S)-2-((R)-1-(4-chlorophenyl)-3-(4-iodophenyl)-3-oxopropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: (E)-3-(4-chlorophenyl)-1-(4-iodophenyl)prop-2-en-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	10 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

24
[ 2510-03-4 ]
[ 947675-12-9 ]
2-((S)-2-((R)-3-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)-3-oxopropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	Stage #1: (E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-bromophenyl)prop-2-en-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	11 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

25
[ 2510-03-4 ]
[ 32120-33-5 ]
2-((S)-2-((R)-3-oxo-1-phenyl-3-(4-(trifluoromethyl)phenyl)propyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: trans-4'-(trifluoromethyl)chalcone With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	12 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

26
[ 2510-03-4 ]
[ 126443-12-7 ]
2-((S)-2-((R)-3-(4-bromophenyl)-1-(4-methoxyphenyl)-3-oxopropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 4'-bromo-4-methoxy-<i>trans</i>-chalcone With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	13 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

27
[ 2510-03-4 ]
[ 36716-01-5 ]
2-((S)-2-((R)-1-(benzo[d][1,3]dioxol-4-yl)-3-(4-bromophenyl)-3-oxopropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-(4-bromophenyl)prop-2-en-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	14 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

28
[ 2510-03-4 ]
[ 39511-11-0 ]
2-((S)-2-((R)-3-oxo-3-phenyl-1-(thiophen-2-yl)propyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	Stage #1: (E)-1-phenyl-3-(thiophen-2-yl)-2-propen-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	16 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

29
[ 2510-03-4 ]
[ 35225-79-7 ]
2-((S)-2-((R,E)-3-oxo-1,5-diphenylpent-4-en-1-yl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: dibenzylideneacetone With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	22 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

30
[ 2510-03-4 ]
[ 614-47-1 ]
2-((S)-2-((R)-3-oxo-1,3-diphenylpropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: 1,3-diphenyl-propen-3-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	1 4.3. Synthesis of Michael adducts 4a-x In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature. 4.3.1. 2-((S)-2-((R)-3-oxo-1,3-diphenylpropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile (4a). The product was obtained as a white solid in 61% yield (122 mg, 0.3 mmol) after purification by chromatography column using 95: 5 Hexane-EtOAc as eluent. 1H NMR (400 MHz, CDCl3) δ: 8.03 (d, J = 7.4 Hz, 1H), 7.74 (dd, J = 8.3, 1.1 Hz, 2H), 7.62-7.48 (m, 2H), 7.43-7.34 (m, 3H), 7.32 (dd, J = 4.2, 3.4 Hz, 5H), 7.25-7.19 m, 1H), 3.66 (dt, J = 11.2, 3.5 Hz, 1H), 3.53 (dd, J = 16.4, 9.6 Hz, 1H), 3.40 (ddd, J = 4.14, 9.70, 11.17 Hz, 1H), 3.08 (ddd, J = 16.5, 11.9, 4.8 Hz, 2H), 2.83 (dd, J = 19.0, 6.5 Hz, 1H), 2.03-1.86 (m, 1H), 1.77 (ddd, J = 9.0, 6.5, 3.2 Hz, 1H). 13C NMR (100 MHz, CDCl3) δ: 197.1; 177.3; 140.9; 140.1; 136.4; 134.1; 133.3; 130.0; 128.9; 128.8; 128.7; 128.6; 128.0; 127.9; 127.4; 127.0; 113.8; 113.6; 80.5; 47.5; 43.2; 41.7; 25.7; 24.4. ee: 96% measured by UPC2 on a Trefoil AMY1 column, CO2/iPrOH gradient [CO2 (1 min), CO2 at 60:40 (4 min), 60:40 (3 min)], 2 mL/min, 35 °C, 137.89 bar, λ = 250.0 nm, tmajor = 3.448 min, tminor = 3.136 min [α]D22 = -140.3 (c = 0.068, CHCl3). HRMS-ES+ m/z: [M + H]+ calcd for C24H22N2O 403.1805; found 403.1804. IR (λmax): 2233, 1687, 1546 cm-1. mp: 161.4-162.9 °C.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

31
[ 2510-03-4 ]
[ 20432-02-4 ]
2-((S)-2-((R)-3-(4-nitrophenyl)-3-oxo-1-phenylpropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: (E)-4'-nitrochalcone With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	2 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

32
[ 2510-03-4 ]
(E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one [ No CAS ]
2-((S)-2-((R)-3-(4-bromophenyl)-3-oxo-1-phenylpropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: (E)-1-(4-bromophenyl)-3-phenylprop-2-en-1-one With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	3 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

33
[ 2510-03-4 ]
[ 22966-19-4 ]
2-((S)-2-((R)-3-(4-methoxyphenyl)-3-oxo-1-phenylpropyl)-3,4-dihydronaphthalen-1(2H)-ylidene)malononitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: trans-4'-methoxychalcone With 9-amino-9-deoxy-epiquinine In 2-methyltetrahydrofuran at 20℃; for 0.5h; Green chemistry; Stage #2: 1,2,3,4-tetrahydro-1-naphthylidene malononitrile In 2-methyltetrahydrofuran at 20℃; for 0.25h; Green chemistry; Stage #3: With trifluoroacetic acid In 2-methyltetrahydrofuran at 20℃; for 96h; Green chemistry; stereoselective reaction;	4 4.3. Synthesis of Michael adducts 4a-x General procedure: In a 10 mL vial was added catalyst 3a (24 mg, 0.075 mmol), chalcone 1a (104 mg, 0.5 mmol) and 2-MeTHF (2.5 mL). This mixture was stirred for 30 min and then added α,α-dicyanoolefin 2a (146 mg, 0.75 mmol). After 15 min, TFA (5.74 μL, 0.075 mmol) was added and the reaction mixture was stirred for 4 days at room temperature.

Reference： [1]Martelli, Lorena S.R.; Vieira, Lucas C.C.; Paixão, Márcio W.; Zukerman-Schpector, Julio; de Souza, Juliana O.; Aguiar, Anna Caroline C.; Oliva, Glaucius; Guido, Rafael V.C.; Corrêa, Arlene G. [Tetrahedron, 2019, vol. 75, # 25, p. 3530 - 3542]

34
[ 33094-66-5 ]
[ 2510-03-4 ]
6-amino-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With cetyltrimethylammonim bromide In water at 20℃; for 24h;	1; 1-6 Example 1 Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90%
90%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product. 4.2.1. 6-Amino-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile (3aa) White solid; 27.9 mg, 90% yield; mp 182.3-183.1 °C; 1H NMR(300 MHz, DMSO-d6) δ 8.20 (d, J = 7.7 Hz, 1H), 8.07 (d, J = 7.5 Hz, 1H), 7.75 (d, J = 8.3 Hz, 1H), 7.60 (t, J = 7.8 Hz, 1H), 7.49-7.41 (m,1H), 7.41-7.29 (m, 3H), 6.36 (s, 2H), 3.17-3.06 (m, 2H), 2.89-2.78 (m,2H); 13C NMR (75 MHz, DMSO-d6) δ 156.2, 142.0, 138.5, 138.0, 132.1,131.2, 128.5, 127.9, 127.9, 126.6, 126.1, 124.8, 123.7, 123.6, 123.5, 121.8,118.7, 112.1, 88.6, 28.5, 24.3; HRMS (ESI-TOF) calcd. for C21H15N2O [M + H]+ 311.1179; found: 311.1170.

Reference： [1]Current Patent Assignee: ZUNYI MEDICAL AND PHARMACEUTICAL COLLEGE - CN110724120, 2020, A Location in patent: Paragraph 0031-0039
[2]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

35
[ 2510-03-4 ]
5-fluoro-2-nitrobenzofuran [ No CAS ]
6-amino-10-fluoro-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With cetyltrimethylammonim bromide In water at 20℃; for 18h;	Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90%
90%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 18h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Current Patent Assignee: ZUNYI MEDICAL AND PHARMACEUTICAL COLLEGE - CN110724120, 2020, A Location in patent: Paragraph 0031-0032; 0040-0043
[2]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

36
[ 2510-03-4 ]
7-fluoro-2-nitrobenzofuran [ No CAS ]
6-amino-8-fluoro-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With cetyltrimethylammonim bromide In water at 20℃; for 20h;	Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90%
87%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 20h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Current Patent Assignee: ZUNYI MEDICAL AND PHARMACEUTICAL COLLEGE - CN110724120, 2020, A Location in patent: Paragraph 0031-0032; 0040-0043
[2]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

37
[ 30335-71-8 ]
[ 2510-03-4 ]
6-amino-8-methoxy-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With cetyltrimethylammonim bromide In water at 20℃; for 36h;	Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90%
87%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Current Patent Assignee: ZUNYI MEDICAL AND PHARMACEUTICAL COLLEGE - CN110724120, 2020, A Location in patent: Paragraph 0031-0032; 0040-0043
[2]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

38
[ 17402-80-1 ]
[ 2510-03-4 ]
C₂₁H₁₄N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With cetyltrimethylammonim bromide In water at 20℃; for 30h;	Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90%
72%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 30h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Current Patent Assignee: ZUNYI MEDICAL AND PHARMACEUTICAL COLLEGE - CN110724120, 2020, A Location in patent: Paragraph 0031-0032; 0040; 0044-0046
[2]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

39
[ 2510-03-4 ]
1-(3-nitro-1H-indol-1-yl)ethanone [ No CAS ]
C₂₃H₁₇N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With cetyltrimethylammonim bromide In water at 20℃; for 48h;	Example 1 General procedure: Add benzo in order to the reaction tubeSix-membered ring dicyanoolefin1a (0.10 mmol),2-nitrobenzofuran 2a (0.12 mmol), adding Cs2CO3 (1 eq, 0.1 mmol),Cetyltrimethylammonium bromide CTAB (5mol%, 0.005mmol) and 1.0mL of water,Stir at room temperature for 24h. TLC detects the basic reaction is complete. The reaction solution is filtered to obtain a filter cake.After dissolving in a small amount of dichloromethane, the sample was loaded and subjected to column chromatography (eluent: V (petroleum ether):V (ethyl acetate) = 5: 1) to obtain compound 4aa as a white solid,Melting point: 182.3-183.1 ° C; yield 90%
62%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 48h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Current Patent Assignee: ZUNYI MEDICAL AND PHARMACEUTICAL COLLEGE - CN110724120, 2020, A Location in patent: Paragraph 0031-0032; 0040; 0044-0046
[2]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

40
[ 2510-03-4 ]
5-chloro-2-nitrobenzo[b]thiophene [ No CAS ]
6-amino-10-chloro-12,13-dihydrobenzo[b]phenanthro [1,2-d]thiophene-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

41
[ 2510-03-4 ]
5-methyl-2-nitrobenzo[b]thiophene [ No CAS ]
6-amino-10-methyl-12,13-dihydrobenzo[b]phenanthro[1,2-d] thiophene-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

42
[ 2510-03-4 ]
C₁₄H₉NO₂S [ No CAS ]
6-amino-9-phenyl-12,13-dihydrobenzo[b]phenanthro[1,2-d]thiophene-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 36h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

43
[ 2510-03-4 ]
5-fluoro-3-nitrobenzo[b]thiophene [ No CAS ]
C₂₁H₁₃FN₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

44
[ 2510-03-4 ]
5-chloro-3-nitrobenzo[b]thiophene [ No CAS ]
C₂₁H₁₃ClN₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

45
[ 2510-03-4 ]
C₁₄H₉NO₂S [ No CAS ]
C₂₇H₁₈N₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 30h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

46
[ 2510-03-4 ]
[ 198135-71-6 ]
C₂₆H₂₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With cetyltrimethylammonim bromide; caesium carbonate; In water; at 20℃; for 36h;	General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Tetrahedron,2020

47
[ 2510-03-4 ]
5-fluoro-3-nitro-N-tosyl-indole [ No CAS ]
C₂₈H₂₀FN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

48
[ 2510-03-4 ]
5-chloro-3-nitro-N-tosyl indole [ No CAS ]
C₂₈H₂₀ClN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

49
[ 2510-03-4 ]
C₁₅H₁₁BrN₂O₄S [ No CAS ]
C₂₈H₂₀BrN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

50
[ 69267-51-2 ]
[ 2510-03-4 ]
6-amino-14,15-dihydronaphtho[2,1-b]phenanthro[1,2-d]furan-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

51
[ 10133-33-2 ]
[ 2510-03-4 ]
6-amino-12,13-dihydrobenzo[b]phenanthro[1,2-d]thiophene-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

52
[ 30335-66-1 ]
[ 2510-03-4 ]
6-amino-10-chloro-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 18h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

53
[ 2510-03-4 ]
C₈H₄ClNO₃ [ No CAS ]
6-amino-11-chloro-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 18h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

54
[ 2510-03-4 ]
[ 30335-67-2 ]
6-amino-10-bromo-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

55
[ 2510-03-4 ]
C₈H₄BrNO₃ [ No CAS ]
6-amino-9-bromo-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

56
[ 2510-03-4 ]
7-bromo-2-nitrobenzofuran [ No CAS ]
6-amino-8-bromo-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

57
[ 2510-03-4 ]
5-methyl-2-nitrobenzofuran [ No CAS ]
6-amino-10-methyl-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

58
[ 2510-03-4 ]
6-methyl-2-nitrobenzofuran [ No CAS ]
6-amino-9-methyl-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

59
[ 30335-72-9 ]
[ 2510-03-4 ]
6-amino-10-methoxy-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

60
[ 2510-03-4 ]
[ 36687-17-9 ]
6-amino-9-methoxy-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

61
[ 56897-23-5 ]
[ 2510-03-4 ]
6-amino-8-ethoxy-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

62
[ 2510-03-4 ]
[ 1541175-01-2 ]
6-amino-10-(tert-butyl)-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

63
[ 2510-03-4 ]
[ 96089-51-9 ]
6-amino-8,10-dibromo-12,13-dihydrophenanthro[2,1-b]benzofuran-5-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With cetyltrimethylammonim bromide; caesium carbonate In water at 20℃; for 24h;	4.2. General procedure for the synthesis of compounds 3, 5, 7, 9 General procedure: To a solution of 1 or 4 or 6 or 8 (0.12 mmol) and 2 (0.10 mmol) in H2O (1 mL) was added Cs2CO3 (32.5 mg, 0.10 mmol) and CTAB(2.0 mg, 5 mol%). The mixture was further stirred at room temperature for the indicated time. Once starting material was consumed (monitored by TLC), the mixture was filtered and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate 8:1 to 3:1) to afford the corresponding product.

Reference： [1]Chen, Yong-Zheng; Quan, Bao-Xue; Yuan, Wei-Cheng; Zhang, Ming-Liang; Zhang, Xiao-Mei; Zhao, Jian-Qiang; Zhuo, Jun-Rui [Tetrahedron, 2020]

64
[ 2510-03-4 ]
[ 66377-63-7 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium tetrahydroborate; oxygen; potassium carbonate In N,N-dimethyl-formamide at 50℃; Molecular sieve;	One-Pot Oxidative Decyanation of Alkylidenemalononitriles to Alcohols; General Procedures A-1 and A-2 General procedure: The corresponding alkylidenemalononitrile (procedure A-1) or alkylmalononitrile (procedure A-2) substrate (1 equiv.) was dissolved in DMF (0.1 M) in a flame-dried Schlenk flask under positive pressure N2 along with 3 Å molecular sieves (~20 mg/mL of solvent). Using an O2 balloon, O2 gas was gently bubbled though the reaction mixture using a long needle through the reaction flask septum. O2 was bubbled for 10 min. After 10 min, NaBH4 (4 equiv. for alkylidenemalononitriles and 2 equiv. for alkylmalononitriles) was then added and the reaction mixture was stirred for 2-5 min (until effervescence stopped). Then, K2CO3 (2 equiv.) was added and the reaction mixture was heated at 50 °C. O2 was bubbled through the mixture until reaction completion. Once completion was achieved (monitored by TLC), the reaction mixture was cooled to rt and the O2 balloon was removed. The excess NaBH4 was slowly quenched with H2O (1 mL) and the reaction mixture was diluted with 2 M HCl(aq) (5 times the reaction volume). The resulting aqueous mixture was extracted with EtOAc three times (2 times the aqueous phase volume). The combined organic layers were washed with 2 M HCl(aq) (equal volume as the organic phase) and brine (equal volume as the organic phase), and dried over Na2SO4. The EtOAc was removed under reduced pressure and the crude was purified via silica gel column chromatography (Hex/EtOAc).

Reference： [1]Emmetiere, Fabien; Grenning, Alexander J. [Synthesis, 2020, vol. 52, # 2, p. 3077 - 3085]

65
[ 2510-03-4 ]
C₁₈H₁₁ClO₃ [ No CAS ]
7-oxo-6-(2-oxo-2-phenylethyl)-13,14-dihydro-6H-phenanthro[2,1-c]chromene-5,5(7H)-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine In ethanol at 80℃; for 10h; Green chemistry; chemoselective reaction;	7,8-Dihydro-6H-benzo[c]chromen-6-ones 3a-i; General Procedure General procedure: Et3N (0.5 mmol) was added to a mixture of the appropriatealkylidene malononitrile derivative 1 (0.5 mmol) and 4-chloro-3-(3-oxo-3-phenylprop-1-en-1-yl)-2H-chromen-2-one 2 (0.5mmol) in anhyd EtOH (1 mL), and the mixture was stirred at 80°C for 10 h until the reaction was complete (TLC). The resultingsolid was isolated by simple filtration and washed twice with96% EtOH.

Reference： [1]Alizadeh, Abdolali; Farajpour, Behnaz; Khanpour, Mojtaba [Synlett, 2021, vol. 32, # 7, p. 697 - 700]

66
[ 2510-03-4 ]
C₁₈H₁₀Cl₂O₃ [ No CAS ]
6-[2-(4-chlorophenyl)-2-oxoethyl]-7-oxo-13,14-dihydro-6H-phenanthro[2,1-c]chromene-5,5(7H)-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine In ethanol at 80℃; for 10h; Green chemistry; chemoselective reaction;	7,8-Dihydro-6H-benzo[c]chromen-6-ones 3a-i; General Procedure General procedure: Et3N (0.5 mmol) was added to a mixture of the appropriatealkylidene malononitrile derivative 1 (0.5 mmol) and 4-chloro-3-(3-oxo-3-phenylprop-1-en-1-yl)-2H-chromen-2-one 2 (0.5mmol) in anhyd EtOH (1 mL), and the mixture was stirred at 80°C for 10 h until the reaction was complete (TLC). The resultingsolid was isolated by simple filtration and washed twice with96% EtOH.

Reference： [1]Alizadeh, Abdolali; Farajpour, Behnaz; Khanpour, Mojtaba [Synlett, 2021, vol. 32, # 7, p. 697 - 700]

67
[ 2510-03-4 ]
C₁₉H₁₃ClO₄ [ No CAS ]
6-[2-(4-methoxyphenyl)-2-oxoethyl]-7-oxo-13,14-dihydro-6H-phenanthro[2,1-c]chromene-5,5(7H)-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With triethylamine In ethanol at 80℃; for 10h; Green chemistry; chemoselective reaction;	7,8-Dihydro-6H-benzo[c]chromen-6-ones 3a-i; General Procedure General procedure: Et3N (0.5 mmol) was added to a mixture of the appropriatealkylidene malononitrile derivative 1 (0.5 mmol) and 4-chloro-3-(3-oxo-3-phenylprop-1-en-1-yl)-2H-chromen-2-one 2 (0.5mmol) in anhyd EtOH (1 mL), and the mixture was stirred at 80°C for 10 h until the reaction was complete (TLC). The resultingsolid was isolated by simple filtration and washed twice with96% EtOH.

Reference： [1]Alizadeh, Abdolali; Farajpour, Behnaz; Khanpour, Mojtaba [Synlett, 2021, vol. 32, # 7, p. 697 - 700]

68
[ 2510-03-4 ]
C₁₉H₁₃ClO₃ [ No CAS ]
6-[2-(4-methylphenyl)-2-oxoethyl]-7-oxo-13,14-dihydro-6H-phenanthro[2,1-c]chromene-5,5(7H)-dicarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With triethylamine In ethanol at 80℃; for 10h; Green chemistry; chemoselective reaction;	7,8-Dihydro-6H-benzo[c]chromen-6-ones 3a-i; General Procedure General procedure: Et3N (0.5 mmol) was added to a mixture of the appropriatealkylidene malononitrile derivative 1 (0.5 mmol) and 4-chloro-3-(3-oxo-3-phenylprop-1-en-1-yl)-2H-chromen-2-one 2 (0.5mmol) in anhyd EtOH (1 mL), and the mixture was stirred at 80°C for 10 h until the reaction was complete (TLC). The resultingsolid was isolated by simple filtration and washed twice with96% EtOH.

Reference： [1]Alizadeh, Abdolali; Farajpour, Behnaz; Khanpour, Mojtaba [Synlett, 2021, vol. 32, # 7, p. 697 - 700]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	2510-03-4	MDL No. :	MFCD00089254
Formula :	C₁₃H₁₀N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ZEJZIWLBVDFZEK-UHFFFAOYSA-N
M.W :	194.23	Pubchem ID :	3586445
Synonyms :

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.23
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	58.11
TPSA :	47.58 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.75 cm/s

Log Po/w (iLOGP) :	2.07
Log Po/w (XLOGP3) :	2.45
Log Po/w (WLOGP) :	2.82
Log Po/w (MLOGP) :	1.76
Log Po/w (SILICOS-IT) :	3.02
Consensus Log Po/w :	2.42

[ CAS No. 2510-03-4 ]

Quality Control of [ 2510-03-4 ]

Related Doc. of [ 2510-03-4 ]

Product Details of [ 2510-03-4 ]

Calculated chemistry of [ 2510-03-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2510-03-4 ]

Application In Synthesis of [ 2510-03-4 ]

[ 2510-03-4 ] Synthesis Path-Upstream 1~2

[ 2510-03-4 ] Synthesis Path-Downstream 1~68

Related Functional Groups of
[ 2510-03-4 ]

Aryls

Alkenyls

Nitriles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-2.88
Solubility :	0.254 mg/ml ; 0.00131 mol/l
Class :	Soluble
Log S (Ali) :	-3.09
Solubility :	0.157 mg/ml ; 0.000808 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.71
Solubility :	0.0377 mg/ml ; 0.000194 mol/l
Class :	Soluble

PAINS :	1.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.4

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 2510-03-4 ]

Quality Control of [ 2510-03-4 ]

Related Doc. of [ 2510-03-4 ]

Product Details of [ 2510-03-4 ]

Calculated chemistry of [ 2510-03-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2510-03-4 ]

Application In Synthesis of [ 2510-03-4 ]

[ 2510-03-4 ] Synthesis Path-Upstream 1~2

[ 2510-03-4 ] Synthesis Path-Downstream 1~68

Related Functional Groups of [ 2510-03-4 ]

Aryls

Alkenyls

Nitriles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 2510-03-4 ]