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[ CAS No. 17649-86-4 ] {[proInfo.proName]}

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Product Details of [ 17649-86-4 ]

CAS No. :17649-86-4 MDL No. :MFCD21604100
Formula : C6H10OS2 Boiling Point : -
Linear Structure Formula :- InChI Key :ICADXNGCMYDRDQ-UHFFFAOYSA-N
M.W : 162.27 Pubchem ID :10942778
Synonyms :

Safety of [ 17649-86-4 ]

Signal Word:Danger Class:9
Precautionary Statements:P261-P264-P270-P271-P273-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:3335
Hazard Statements:H302-H312-H315-H319-H332-H335-H410-H372 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 17649-86-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 17649-86-4 ]

[ 17649-86-4 ] Synthesis Path-Downstream   1~85

  • 2
  • [ 100643-27-4 ]
  • [ 17649-86-4 ]
  • 5-methylthio-7-methyl-5-deazapteridine [ No CAS ]
  • 3
  • [ 17649-86-4 ]
  • [ 870-63-3 ]
  • [ 84735-54-6 ]
YieldReaction ConditionsOperation in experiment
85% With lithium diisopropyl amide In tetrahydrofuran at -70℃;
With lithium diisopropyl amide 1) THF, -78 deg C, 15 min., 2) RT, 1h; Yield given. Multistep reaction;
With lithium diisopropyl amide 1.) THF, -78 deg C, 15 min, 2.) THF, from -78 deg C to RT, 1.5 h; Yield given. Multistep reaction;
  • 4
  • [ 5780-61-0 ]
  • [ 14527-26-5 ]
  • [ 17649-86-4 ]
  • 5
  • [ 5780-61-0 ]
  • [ 5188-07-8 ]
  • [ 17649-86-4 ]
YieldReaction ConditionsOperation in experiment
87% In diethyl ether for 1h; Heating / reflux; 23 Example 23: Synthesis of 3-amino-4- (4-methanesulfonyl-phenyl)-6-methyl-thieno [2,3- [B] PYRIDINE-2-CARBOXYLIC] acid amide Sodium thiomethoxide (1.40 g, 20 mmol) was suspended in ether (20 mL) and the above dichlorovinyl ketone (10 mmol), dissolved in ether (10 mL), was added dropwise. The resulting solution was refluxed for 1 h, filtered, and the precipitate washed with ether. The combined filtrates were evaporated to yield 1.4 g (87%) of the desired dimethylthiovinyl ketone.
75% In diethyl ether for 0.5h; Heating;
  • 6
  • [ 17649-86-4 ]
  • [ 77953-59-4 ]
YieldReaction ConditionsOperation in experiment
94% With zinc In tetrahydrofuran; water; acetic acid at 0℃;
55% With sodium tetrahydroborate; acetic acid for 3h; Ambient temperature;
With sodium tetrahydroborate In acetic acid
  • 7
  • [ 75-15-0 ]
  • [ 67-64-1 ]
  • [ 74-88-4 ]
  • [ 17649-86-4 ]
YieldReaction ConditionsOperation in experiment
70% Stage #1: acetone With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.25h; Stage #2: carbon disulfide; methyl iodide In tetrahydrofuran at 20℃; for 10h;
65% Stage #1: carbon disulfide; acetone With sodium tert-butoxide In benzene at 10 - 20℃; for 3h; Stage #2: methyl iodide In benzene at 10 - 20℃;
64% Stage #1: carbon disulfide; acetone With sodium t-butanolate In tetrahydrofuran at 20℃; for 3h; Stage #2: methyl iodide In tetrahydrofuran at 10 - 20℃;
61% Stage #1: carbon disulfide; acetone With sodium t-butanolate In tetrahydrofuran at 10 - 20℃; for 3h; Stage #2: methyl iodide In tetrahydrofuran at 10 - 20℃; A solution of acetone (0.96 mL, 13.1 mmol) in carbon disulfide (1 g, 13.1 mmol) was added to a suspension of sodium tert-butoxide (2.5 g, 26.2 mmol) in THF (30 mL) whilenot allowing the temperature to exceed 10 °C. The reaction mixture was stirred at RT for 3 h and Mel (1.6 mL, 26.2 mmol) was added at 10 °C and the resulting solution was stirred overnight at RT. The reaction mixture was diluted with EtOAc (100 mL), washed with water (30 mL x 2) and the organic layer was dried over MgSO4, and filtered. The filtrate was concentrated in vacuo and the crude was purified by triturating with PE (30 mL) to give 4,4-bis(methylthio)but-3-en-2-one (500 mg, 61%) as a yellow solid.
59% Stage #1: carbon disulfide; acetone With potassium <i>tert</i>-butylate Inert atmosphere; Stage #2: methyl iodide at 0 - 20℃;
51% Stage #1: acetone With sodium hydride In tetrahydrofuran at 0℃; for 0.333333h; Stage #2: carbon disulfide In tetrahydrofuran at 0℃; for 0.5h; Stage #3: methyl iodide In tetrahydrofuran at 0 - 20℃; for 3h;
41% Stage #1: carbon disulfide; acetone With sodium t-butanolate In toluene at 0℃; for 4h; Inert atmosphere; Stage #2: methyl iodide In methanol; toluene for 0.25h; Reflux;
KF/Al2O3; multistep reaction: one-pot synthesis of ketene dithioacetals; other active methylene compounds;
With sodium hydride Multistep reaction;
With lithium diisopropyl amide LHMDS, THF, HMPT; Yield given. Multistep reaction;
With potassium fluoride on basic alumina 1.) r.t., 1 h, 2.) 16 h; Yield given. Multistep reaction;
With lithium diisopropyl amide In tetrahydrofuran
With sodium hydride 1.) 0 deg C; 2.) benzene; Multistep reaction;
Stage #1: acetone With potassium <i>tert</i>-butylate In tetrahydrofuran for 0.25h; Stage #2: carbon disulfide; methyl iodide In tetrahydrofuran at 20℃; for 14h; 3.1. General procedure for the synthesis of 3-oxo-bis(methylthio)ketenacetals 2a-p General procedure: To a solution of KOtBu (2.0 equiv) in dry THF (1.0 mL/mmol) was dropwise added 1a-p (1.0 equiv) and the mixture was stirred for 15 min. Subsequently, carbon disulfide (1.0 equiv) and iodomethane (2.0 equiv) were added and the mixture was stirred at 20 °C for 14 h. Water was added and the organic layer was separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by chromatography (silica gel, heptanes/EtOAc20:1). The synthesis of 2a-m and 2o,p has been previously reported.
With sodium hydride In N,N-dimethyl-formamide; toluene; mineral oil at 0℃; for 24h;
With sodium hydride In tetrahydrofuran Cooling;
With sodium hydride In N,N-dimethyl-formamide; toluene at 0℃; for 24h;
With sodium t-butanolate In tetrahydrofuran at 20℃; 6 F1 synthesis In acetone (30 mmol) solution in tetrahydrofuran (30 ml), Carbon disulfide (30 mmol),was added to the methyliodide (60 mmol) and sodium t- butoxide (60 mmol).The reaction mixture was stirred at room temperature overnight. When the reaction iscomplete, the mixture was diluted with ethyl acetate and washed with brine. The organiclayer was dried over anhydrous MgSO4 and concentrated in vacuo. Purification of thecrude residue by silica gel flash column chromatography to generate the F1.
6.8 g Stage #1: carbon disulfide; acetone With sodium t-butanolate In toluene at 0℃; for 4h; Inert atmosphere; Stage #2: methyl iodide In methanol at 70℃; for 1h;

Reference: [1]Location in patent: scheme or table Lubbe, Mathias; Klassen, Renske; Trabhardt, Tiana; Villinger, Alexander; Langer, Peter [Synlett, 2008, # 15, p. 2331 - 2333]
[2]Dhanalakshmi, Pandi; Shanmugam, Sivakumar [RSC Advances, 2014, vol. 4, # 56, p. 29493 - 29501]
[3]Soares De Melo, Candice; Singh, Vinayak; Myrick, Alissa; Simelane, Sandile B.; Taylor, Dale; Brunschwig, Christel; Lawrence, Nina; Schnappinger, Dirk; Engelhart, Curtis A.; Kumar, Anuradha; Parish, Tanya; Su, Qin; Myers, Timothy G.; Boshoff, Helena I. M.; Barry, Clifton E.; Sirgel, Frederick A.; Van Helden, Paul D.; Buchanan, Kirsteen I.; Bayliss, Tracy; Green, Simon R.; Ray, Peter C.; Wyatt, Paul G.; Basarab, Gregory S.; Eyermann, Charles J.; Chibale, Kelly; Ghorpade, Sandeep R. [Journal of Medicinal Chemistry, 2021, vol. 64, # 1, p. 719 - 740]
[4]Current Patent Assignee: BIAL R D INVESTMENTS - WO2017/176960, 2017, A1 Location in patent: Paragraph 00296
[5]Zhang, Jinsong; Chang, Xiao; Bowman, Erich C.; Holt, Carter J.; Lodewyk, Michael W.; Miller, Randy M.; Xia, Guangming [Journal of Organic Chemistry, 2015, vol. 80, # 18, p. 9292 - 9296]
[6]He, Jun; Man, Zengming; Shi, Yinping; Li, Chuan-Ying [Journal of Organic Chemistry, 2015, vol. 80, # 9, p. 4816 - 4823]
[7]Location in patent: experimental part Smyth, Lynette A.; Matthews, Thomas P.; Horton, Peter N.; Hursthouse, Michael B.; Collins, Ian [Tetrahedron, 2010, vol. 66, # 15, p. 2843 - 2854]
[8]Villemin; Alloum [Synthesis, 1991, # 4, p. 301 - 303]
[9]Huang, Zhi-Tang; Shi, Xian [Chemische Berichte, 1990, vol. 123, p. 541 - 547]
[10]Dieter; Lin; Dieter [Journal of Organic Chemistry, 1984, vol. 49, # 17, p. 3183 - 3195]
[11]Villemin; Alloum [Synthesis, 1991, # 4, p. 301 - 303]
[12]Dieter,R.K.; Silks,L.A.; Fishpaugh,J.R. [Journal of the American Chemical Society, 1985, vol. 107, p. 4679]
[13]Mohanalingam; Nethaji; Das, Puspendu Kumar [Journal of Molecular Structure, 1996, vol. 378, # 3, p. 177 - 188]
[14]Lubbe, Mathias; Bendrath, Franziska; Trabhardt, Tiana; Villinger, Alexander; Fischer, Christine; Langer, Peter [Tetrahedron, 2013, vol. 69, # 29, p. 5998 - 6007]
[15]Mao, Zhifeng; Huang, Fei; Yu, Haifeng; Chen, Jiping; Yu, Zhengkun; Xu, Zhaoqing [Chemistry - A European Journal, 2014, vol. 20, # 12, p. 3439 - 3445]
[16]Singh, Surjeet; Althagafi, Ismail; Yadav, Pratik; Panwar, Rahul; Kumar, Abhinav; Pratap, Ramendra [Tetrahedron, 2014, vol. 70, # 46, p. 8879 - 8884]
[17]Wu, Ping; Wang, Liandi; Wu, Kaikai; Yu, Zhengkun [Organic Letters, 2015, vol. 17, # 4, p. 868 - 871]
[18]Current Patent Assignee: INSTITUT PASTEUR; JUSIKHOESA QUROSCIENCE - KR101480674, 2015, B1 Location in patent: Paragraph 0121-0123
[19]Apte, Shruti; Arora, Shilpi; Audia, James E.; Bradley, William D.; Brenneman, Jehrod; Bruderek, Kamil; Cantone, Nico; Cummings, Richard T.; Gehling, Victor S.; Khanna, Avinash; Levell, Julian R.; Moine, Ludivine; Ramakrishnan, Ashwin; Sims, Robert J.; Stuckey, Jacob I.; Trojer, Patrick; Côté, Alexandre [ACS Medicinal Chemistry Letters, 2020, vol. 11, # 6, p. 1205 - 1212]
  • 8
  • [ 13781-53-8 ]
  • [ 17649-86-4 ]
  • (E)-3-Methylsulfanyl-5-oxo-2-thiophen-3-yl-hex-3-enenitrile [ No CAS ]
  • 9
  • [ 17649-86-4 ]
  • trans-decalin-2-one [ No CAS ]
  • 3-hydroxy-1-(methylthio)-5,6,7,8,8a,9,10,10a-octahydroanthracene [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;
  • 10
  • [ 17649-86-4 ]
  • [ 589-92-4 ]
  • 7-hydroxy-3-methyl-5-(methylthio)-1,2,3,4-tetrahydronaphthalene [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;
  • 11
  • [ 17649-86-4 ]
  • [ 830-13-7 ]
  • 3-hydroxy-1-(methylthio)-5,6,7,8,9,10,11,12,13,14-decahydrobenzododecene [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;
  • 12
  • [ 17649-86-4 ]
  • [ 502-42-1 ]
  • 3-hydroxy-1-(methylthio)-6,7,8,9-tetrahydro-5H-benzocycloheptene [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃;
68% With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;
  • 13
  • [ 615-15-6 ]
  • [ 17649-86-4 ]
  • [ 528877-71-6 ]
YieldReaction ConditionsOperation in experiment
92% Stage #1: 2-Methyl-1H-benzimidazole With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Stage #2: 4,4-bis(methylthio)but-3-en-2-one In tetrahydrofuran at 0 - 20℃;
  • 15
  • [ 17649-86-4 ]
  • [ 123-11-5 ]
  • [ 89812-52-2 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide In ethanol at 10 - 20℃; for 0.5h;
90% With sodium hydroxide In ethanol at 0 - 20℃; for 1.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
57% With potassium hydroxide In methanol; water at 20℃; for 12h;
With sodium hydroxide In ethanol at 20℃; for 2h;

  • 16
  • [ 17649-86-4 ]
  • [ 120-14-9 ]
  • [ 117672-14-7 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide In ethanol at 10 - 20℃; for 0.5h;
57.09% With potassium hydroxide In methanol; water at 20℃; for 12h;
  • 17
  • [ 7357-70-2 ]
  • [ 17649-86-4 ]
  • C8H8N2S2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With sodium isopropylate In isopropyl alcohol Reflux;
95% With sodium In isopropyl alcohol for 30h; Heating / reflux; 23 Example 23: Synthesis of 3-amino-4- (4-methanesulfonyl-phenyl)-6-methyl-thieno [2,3- [B] PYRIDINE-2-CARBOXYLIC] acid amide Sodium (533 mg, 23.2 mmol) was dissolved in isopropanol (50 mL) under heating. 2- Cyanothioacetamide (2.1 g, 21 mmol) was added and the solution was stirred for 5 min of at room temperature. The above dimethylthiovinyl ketone (3.4 g, 21 mmol) was added to the reaction mixture and the solution was refluxed until starting material disappeared (-30 h). The solvent was evaporated and the residue was dissolved in water. The aqueous solution was filtered, acidified to pH 3, and the precipitate was filtered off. The precipitate was washed with ether and then with hexane to give 3.9 g (95%) of the desired thiopyridine.
  • 18
  • [ 50-00-0 ]
  • [ 17649-86-4 ]
  • [ 1059605-54-7 ]
YieldReaction ConditionsOperation in experiment
85% With hydrogenchloride In tetrahydrofuran; water at 20℃; for 2h;
  • 19
  • [ 15908-50-6 ]
  • [ 17649-86-4 ]
YieldReaction ConditionsOperation in experiment
95% With sulfuric acid In dichloromethane at 0 - 20℃; for 10h;
95% With sulfuric acid In dichloromethane at 0 - 20℃; for 10h;
95% With sulfuric acid In dichloromethane at 0 - 20℃; for 10h;
80% With sodium hydroxide In acetonitrile for 0.5h; Reflux;
74.3% With sulfuric acid In dichloromethane 34.2 Step 2. 4,4-bis(methylthio)-3-buten-2-one (34c) Compound 34b (17g, 83.3mmol) was dissolved in dichloromethane,Slowly add 10 mL of concentrated sulfuric acid dropwise and stir overnight. After the reaction, the reaction solution was neutralized to weak acidity with dilute hydrochloric acid (2N) in an ice bath, extracted with ethyl acetate and water, the organic phases were combined, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain The yellow solid is 10.0 g, and the yield is 74.3%.
With sulfuric acid In dichloromethane at 20℃; for 10h;
With sulfuric acid In dichloromethane at 0 - 20℃;
With sulfuric acid In dichloromethane at 0 - 20℃;

  • 20
  • [ 17649-86-4 ]
  • [ 78133-88-7 ]
  • [ 1088703-79-0 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 4,4-bis(methylthio)but-3-en-2-one; 1,3-bis(trimethylsiloxy)-1-methoxypenta-1,3-diene With titanium tetrachloride In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere; Stage #2: With hydrogenchloride In dichloromethane; water regioselective reaction;
65% With titanium tetrachloride In dichloromethane at -78 - 20℃; for 14h; Inert atmosphere; regioselective reaction; 3.3. General procedure for the synthesis of 5a-ap General procedure: To a solution of 2 (1.0 mmol) and diene 4 (2.0 mmol) in CH2Cl2(2 mL) was added TiCl4 (1.0 mmol) at -78 °C under argon. The temperature of the reaction mixture was allowed to rise to 20 °C during 14 h, and an aqueous HCl solution (10%, 10 mL) was added. The organic layer was separated, and the aqueous layer was extracted with CH2Cl2 (310 mL). The combined organic layers weredried (Na2SO4), filtered and concentrated in vacuo. After column chromatography (silica gel, heptanes/EtOAc10:1), 5 was isolated.
  • 21
  • 3,3,9-trimethyl-3,4-dihydro-2H-acridin-1-one [ No CAS ]
  • [ 17649-86-4 ]
  • [ 1194451-71-2 ]
YieldReaction ConditionsOperation in experiment
72% Stage #1: 3,3,9-trimethyl-3,4-dihydro-2H-acridin-1-one; 4,4-bis(methylthio)but-3-en-2-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With hydrogenchloride In water Cooling with ice;
  • 22
  • [ 14428-46-7 ]
  • [ 17649-86-4 ]
  • [ 1194451-68-7 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 9-methyl-3,4-dihydroacridin-1(2H)-one; 4,4-bis(methylthio)but-3-en-2-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: With hydrogenchloride In water Cooling with ice;
  • 23
  • [ 17649-86-4 ]
  • [ 107-91-5 ]
  • [ 57663-05-5 ]
YieldReaction ConditionsOperation in experiment
91.9% With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol at 85℃; 34.3 Step 3. 6-Methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile (34d) Compound 34c (10 g, 61.6 mmol), cyanoacetamide (5.2 g, 61.6 mmol), potassium tert-butoxide (13.8 g, 112.2 mmol) were dissolved in 250 mL tert-butanol, and reacted at 85°C overnight. After the reaction, water was added to the reaction solution until it was clear, and then the reaction solution was neutralized to acidity with dilute hydrochloric acid (2N), stirred uniformly, and filtered to obtain 10.2 g of a light yellow solid, with a yield of 91.9%.
74% With sodium t-butanolate In <i>tert</i>-butyl alcohol at 80℃; for 12h; 3 Step 3:
Synthesis of 6-methyl-4-(methylthio)-2-oxo-1,2-dihydropyridine-3-carbonitrile
To a solution of 4,4-bis(methylthio)but-3-en-2-one (2.9 g, 18 mmol) and 2-cyanoacetamide (1.5 g, 18 mmol) in tert-butanol (50 mL) was added sodium tert-butoxide (1.9 g, 20 mmol). The mixture was stirred at 80° C. for 12 h (two batches of the reaction were performed and combined at this stage). Water (20 mL) was added and the pH adjusted to 5-6 with 10% hydrochloric acid. The resulting mixture was filtered, and the filter cake was washed with petroleum ether (20 mL*2) then the cake was dried under vacuum to give the title compound (4.8 g, 74% yield) as an off-white solid, which was used in the next step without further purification. LCMS [M+H]+ m/z: calc'd 181.0; found 181.0. 1H NMR (400 MHz, Dimethylsulfoxide-d6) δ 6.27 (s, 1H), 2.56 (s, 3H), 2.25 (s, 3H).
74% With sodium t-butanolate In <i>tert</i>-butyl alcohol at 80℃; for 12h; 1.3 Step 3: Synthesis of 6-methyl-4-(methylthio)-2-oxo-l,2-dihydropyridine-3- carbonitrile To a solution of 4,4-bis(methylthio)but-3-en-2-one (2.9 g, 18 mmol) and 2- cyanoacetamide (1.5 g, 18 mmol) in tert-butanol (50 mL) was added sodium tert-butoxide (1.9 g, 20 mmol). The mixture was stirred at 80 °C for 12 h (two batches of the reaction were performed and combined at this stage). Water (20 mL) was added and the pH adjusted to 5-6 with 10% hydrochloric acid. The resulting mixture was filtered, and the filter cake was washed with petroleum ether (20 mL x 2) then the cake was dried under vacuum to give the title compound (4.8 g, 74% yield) as an off-white solid, which was used in the next step without further purification. LCMS [M+H]+ m/z: calc’d 181.0; found 181.0. 1H NMR (400 MHz, dimethylsulfoxide-i/6) d 6.27 (s, 1H), 2.56 (s, 3H), 2.25 (s, 3H).
59% With sodium isopropylate In isopropyl alcohol for 2h; Reflux;
With sodium t-butanolate In <i>tert</i>-butyl alcohol at 80℃; for 12h; 3 Step 3: Synthesis of 6-methyl-4-(methylthio)-2-oxo-l,2-dihydropyridine-3- carbonitrile (A3) To a solution of 4,4-bis(methylthio)but-3-en-2-one (2.9 g, 18 mmol, 1.0 equiv) and 2-cyanoacetamide (1.5 g, 18 mmol, 1.0 equiv) in 2-methylpropan-2-ol (50 mL) was added i-BuONa (1.9 g, 20 mmol, 1.1 equiv). The mixture was stirred at 80 °C for 12 h. Two batches of the reaction were performed and combined at this stage. Water (20 mL) was added and the pH was adjusted to 5-6 with 10% HC1 solution. Then the resulting mixture was filtered, and the filter cake was washed with petroleum ether (petroleum ether) (20 mL * 2) to give crude A3, 6-methyl-4-(methylthio)-2-oxo-l,2-dihydropyridine-3- carbonitrile (4.8 g, 27 mmol, 74% yield), as an off-white solid. LCMS [M+H]+ m/z: calc'd 181.04; found 181.0. 1H NMR (400 MHz, DMSO-i) δ 6.27 (s, 1H), 2.56 (s, 3H), 2.25 (s, 3H)
In <i>tert</i>-butyl alcohol at 80℃; for 12h;

  • 24
  • [ 17649-86-4 ]
  • [ 1271024-67-9 ]
  • [ 1271025-08-1 ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 4,4-bis(methylthio)but-3-en-2-one In N,N-dimethyl-formamide at 20℃; for 22h; Inert atmosphere;
61.5% Stage #1: 4-amino-N,N-dicyclopropyl-6-ethyl-1-methyl-1,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7-carboxamide With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 4,4-bis(methylthio)but-3-en-2-one In N,N-dimethyl-formamide for 72h; 72.72B 72B Preparation of (Z)-N.N-dicvclopropyl-6-ethyl- 1 -methyl-4-( 1 - (methylthio)-3-oxobut-l-enylamino)-1.6-dihydroimidazo[4.5-dlpyrrolo[2.3- blpyridine-7-carboxamide[00351] Sodium hydride (2.84 g, 71.1 mmol) was added to a solution of 4-amino- N,N-dicyclopropyl-6-ethyl-l-methyl-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3- b]pyridine-7-carboxamide (example 1J, 8.02 g, 23.70 mmol) in DMF (60 mL) and the reaction mixture stirred at room temperature for 1 h. 4,4-bis(methylthio)but-3-en-2- one (example 70A, 5.77 g, 35.5 mmol) in DMF (10 ml) was added and stirring continued for three days. LC/MS showed about 75% completion. The reaction mixture was diluted with ethyl acetate and water was added. An off-white precipitate formed and was collected by filtration to give 5.1 g of product. The filtrate was transferred to a separatory funnel. The layers were separated and the aqueous layer was extracted with dichloromethane (3x50 ml), the combined organic layers were washed with saturated sodium bicarbonate and dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using an ISCO system (220 g column, eluting with 2-8% methanol / dichloromethane) to give (Z)-N,N-dicyclopropyl-6-ethyl-l-methyl-4-(l-(methylthio)- 3-oxobut-l-enylamino)-l,6-dihydroimidazo[4,5-d]pyrrolo[2,3-b]pyridine-7- carboxamide (6.6 g, 61.5% yield) along with 2.2 g of recovered 1J.[00352] MS (ESI) m/z 453.3 (M+H).[00353] XH NMR (400 MHz, DMSO-d6) δ: 14.42 (s, 1H), 8.16 (s, 1H), 7.24 (s, 1H), 5.54 (s, 1H), 4.52 (q, J = 7.0 Hz, 2H), 4.05 (s, 3H), 2.89 - 2.97 (m, 2H), 2.43 (s, 3H), 2.14 (s, 3H), 1.34 (t, J = 7.0 Hz, 3H), 0.71 - 0.80 (m, 4H), 0.63 - 0.70 (m, 4H).
  • 25
  • [ 75-15-0 ]
  • [ 67-64-1 ]
  • [ 17649-86-4 ]
YieldReaction ConditionsOperation in experiment
71% With sodium t-butanolate In benzene at 10 - 20℃; 72.72A 72A Preparation of 4,4-bis(methyrthio)but-3-en-2-one[00349] A solution of acetone (2.205 mL, 30.0 mmol) in carbon disulfide (1.81 mL, 30.0 mmol) was added to a suspension of sodium tert-butoxide (5.76 g, 60.0 mmol) in benzene (30 mL) while keeping the reaction temperature not exceeding 10 °C. The reaction mixture was stirred at room temperature for 3h and iodomethane (3.75 mL, 60.0 mmol) was added at 10 °C. The resulting reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate and washed twice with water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using an automated ISCO system (80 g column, eluting with 10-35% ethyl acetate / hexanes) to give 4,4-bis(methylthio)but-3-en-2-one (3.456 g, 71.0 % yield) as a yellow solid.[00350] XH NMR (400 MHz, CDC13) δ: 6.04 (s, 1H), 2.47 (s, 3H), 2.45 (s, 3H), 2.20 (s, 3H).
  • 26
  • [ 17649-86-4 ]
  • [ 1679-18-1 ]
  • [ 1315282-85-9 ]
YieldReaction ConditionsOperation in experiment
75% With tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate; caesium carbonate In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; optical yield given as %de; stereoselective reaction;
  • 27
  • [ 17649-86-4 ]
  • [ 98-80-6 ]
  • (E)-4-Methylthio-4-phenyl-3-buten-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate; caesium carbonate In tetrahydrofuran at 50℃; for 2h; Inert atmosphere; optical yield given as %de; stereoselective reaction;
  • 28
  • [ 17649-86-4 ]
  • [ 1146-43-6 ]
  • [ 1413391-82-8 ]
YieldReaction ConditionsOperation in experiment
42% Stage #1: N-(4-hydroxyphenyl)-4-methylbenzenesulfonamide With [bis(acetoxy)iodo]benzene; boron trifluoride diethyl etherate In dichloromethane; acetonitrile at 20℃; for 0.166667h; Stage #2: 4,4-bis(methylthio)but-3-en-2-one With copper(ll) bromide In dichloromethane; acetonitrile at 20℃; for 0.5h; 4.3.5 N-[3-Acetyl-2-(methylthio)benzofuran-5-yl]-4-methylbenzenesulfonamide (3e) General procedure: To a 50 mL round bottomed flask containing N-(4-hydroxyphenyl)-benzenesulfonamide (1 mmol) dissolved in 10 mL of acetonitrile was added dropwise PhI(OAc)2 (483 mg, 1.5 mmol) in 5 mL of CH2Cl2 and 0.1 mL of 1 mol/L BF3·Et2O. After stirring at room temperature for 10 min, ketene S,S-acetals or N,S-acetals (1 mmol) and CuBr2 (4.6 mg, 0.02 mmol) were added and the solution was continued to stir, while monitoring the reaction by TLC. After the completion of the reaction (about 30 min), the solvent was evaporated under reduced pressure and 20 mL of saturated sodium carbonate aqueous was added. CH2Cl2 was used to extract (3×20 mL), the combined organic layers were washed with brine and dried over anhydrous MgSO4. The expected benzofurans were obtained after column chromatography; elution used a mixed solvent of petroleum ether and acetone.
  • 29
  • [ 17649-86-4 ]
  • [ 104-88-1 ]
  • [ 89812-53-3 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide In ethanol at 10 - 20℃; for 0.5h;
99% With sodium hydroxide In ethanol at 0 - 20℃; for 0.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
76% With potassium hydroxide In methanol; water at 20℃; for 12h; General procedure :(E)-5-(4-Substitutedphenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one (6a-h) General procedure: To a solution of 1,1-dithiomethyl-1-en-3-butenone (5) (1.62 gm, 10 mmol) in methanol (40 ml), substituted benzaldehydes (4) (10 mmol) were added, followed by aqueous KOH solution (1.12 gm, 20 mmol, in 10 ml of water), the resulting reaction mixture was stirred at room temperature for 12 hr. It was concentrated in vacuo, poured into water (100 ml) and extracted with dichloromethane (50 ml x 3). The combined extract was washed with water (100 ml x 2), brine solution (50 ml x 2), and dried(Na2SO4). The solvent was removed in vacuo and the resulting crude product was column chromatographed (SiO2, 60-120 mesh). Elution with mixture of ethylacetate in hexane furnished compounds 6a-h.
With sodium hydroxide In ethanol at 20℃; for 2h;

  • 30
  • [ 17649-86-4 ]
  • [ 89-98-5 ]
  • [ 128951-04-2 ]
YieldReaction ConditionsOperation in experiment
50% With potassium hydroxide In methanol; water at 20℃; for 12h; (E)-5-(2-Chlorophenyl)-1,1-bis (methylthio)penta-1,4-dien-3-one (6b) General procedure: To a solution of 1,1-dithiomethyl-1-en-3-butenone (5) (1.62 gm, 10 mmol) in methanol (40 ml), substituted benzaldehydes (4) (10 mmol) were added, followed by aqueous KOH solution (1.12 gm, 20 mmol, in 10 ml of water), the resulting reaction mixture was stirred at room temperature for 12 hr. It was concentrated in vacuo, poured into water (100 ml) and extracted with dichloromethane (50 ml x 3). The combined extract was washed with water (100 ml x 2), brine solution (50 ml x 2), and dried(Na2SO4). The solvent was removed in vacuo and the resulting crude product was column chromatographed (SiO2, 60-120 mesh). Elution with mixture of ethylacetate in hexane furnished compounds 6a-h.
  • 31
  • [ 17649-86-4 ]
  • [ 555-16-8 ]
  • [ 128951-03-1 ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide In ethanol at 0 - 20℃; for 2h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
71% With potassium hydroxide In methanol; water at 20℃; for 12h; (E)-5-(4-Nitrophenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one (6c) General procedure: To a solution of 1,1-dithiomethyl-1-en-3-butenone (5) (1.62 gm, 10 mmol) in methanol (40 ml), substituted benzaldehydes (4) (10 mmol) were added, followed by aqueous KOH solution (1.12 gm, 20 mmol, in 10 ml of water), the resulting reaction mixture was stirred at room temperature for 12 hr. It was concentrated in vacuo, poured into water (100 ml) and extracted with dichloromethane (50 ml x 3). The combined extract was washed with water (100 ml x 2), brine solution (50 ml x 2), and dried(Na2SO4). The solvent was removed in vacuo and the resulting crude product was column chromatographed (SiO2, 60-120 mesh). Elution with mixture of ethylacetate in hexane furnished compounds 6a-h.
  • 32
  • [ 17649-86-4 ]
  • [ 99-61-6 ]
  • [ 1374036-04-0 ]
YieldReaction ConditionsOperation in experiment
64% With potassium hydroxide In methanol; water at 20℃; for 12h; (E)-5-(3-Nitrophenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one (6d) General procedure: To a solution of 1,1-dithiomethyl-1-en-3-butenone (5) (1.62 gm, 10 mmol) in methanol (40 ml), substituted benzaldehydes (4) (10 mmol) were added, followed by aqueous KOH solution (1.12 gm, 20 mmol, in 10 ml of water), the resulting reaction mixture was stirred at room temperature for 12 hr. It was concentrated in vacuo, poured into water (100 ml) and extracted with dichloromethane (50 ml x 3). The combined extract was washed with water (100 ml x 2), brine solution (50 ml x 2), and dried(Na2SO4). The solvent was removed in vacuo and the resulting crude product was column chromatographed (SiO2, 60-120 mesh). Elution with mixture of ethylacetate in hexane furnished compounds 6a-h.
  • 33
  • [ 17649-86-4 ]
  • [ 459-57-4 ]
  • [ 1374036-03-9 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide In ethanol at 0 - 20℃; for 1.33333h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
34% With potassium hydroxide In methanol; water at 20℃; for 12h; (E)-5-(4-Fluorophenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one (6e) General procedure: To a solution of 1,1-dithiomethyl-1-en-3-butenone (5) (1.62 gm, 10 mmol) in methanol (40 ml), substituted benzaldehydes (4) (10 mmol) were added, followed by aqueous KOH solution (1.12 gm, 20 mmol, in 10 ml of water), the resulting reaction mixture was stirred at room temperature for 12 hr. It was concentrated in vacuo, poured into water (100 ml) and extracted with dichloromethane (50 ml x 3). The combined extract was washed with water (100 ml x 2), brine solution (50 ml x 2), and dried(Na2SO4). The solvent was removed in vacuo and the resulting crude product was column chromatographed (SiO2, 60-120 mesh). Elution with mixture of ethylacetate in hexane furnished compounds 6a-h.
  • 34
  • [ 2426-87-1 ]
  • [ 17649-86-4 ]
  • [ 1374036-06-2 ]
YieldReaction ConditionsOperation in experiment
67% With potassium hydroxide In methanol; water at 20℃; for 12h; (E)-5-(4-(benzyloxy)-3-methoxyphenyl)-1,1-bis (methylthio)penta-1,4-dien-3-one (6f) General procedure: To a solution of 1,1-dithiomethyl-1-en-3-butenone (5) (1.62 gm, 10 mmol) in methanol (40 ml), substituted benzaldehydes (4) (10 mmol) were added, followed by aqueous KOH solution (1.12 gm, 20 mmol, in 10 ml of water), the resulting reaction mixture was stirred at room temperature for 12 hr. It was concentrated in vacuo, poured into water (100 ml) and extracted with dichloromethane (50 ml x 3). The combined extract was washed with water (100 ml x 2), brine solution (50 ml x 2), and dried(Na2SO4). The solvent was removed in vacuo and the resulting crude product was column chromatographed (SiO2, 60-120 mesh). Elution with mixture of ethylacetate in hexane furnished compounds 6a-h.
  • 35
  • [ 17649-86-4 ]
  • [ 10040-98-9 ]
  • [ 1374036-07-3 ]
YieldReaction ConditionsOperation in experiment
33% With potassium hydroxide In methanol; water at 20℃; for 12h; (E)-5-(4-(1H-imidazol-1-yl)phenyl)-1,1-bis(methylthio) penta-1,4-dien-3-one (6g) General procedure: To a solution of 1,1-dithiomethyl-1-en-3-butenone (5) (1.62 gm, 10 mmol) in methanol (40 ml), substituted benzaldehydes (4) (10 mmol) were added, followed by aqueous KOH solution (1.12 gm, 20 mmol, in 10 ml of water), the resulting reaction mixture was stirred at room temperature for 12 hr. It was concentrated in vacuo, poured into water (100 ml) and extracted with dichloromethane (50 ml x 3). The combined extract was washed with water (100 ml x 2), brine solution (50 ml x 2), and dried(Na2SO4). The solvent was removed in vacuo and the resulting crude product was column chromatographed (SiO2, 60-120 mesh). Elution with mixture of ethylacetate in hexane furnished compounds 6a-h.
  • 36
  • 4-(1,3,4-triazol-1-yl)-benzaldehyde [ No CAS ]
  • [ 17649-86-4 ]
  • [ 1412454-66-0 ]
YieldReaction ConditionsOperation in experiment
29% With potassium hydroxide In methanol; water at 20℃; for 12h; (E)-5-(4-(4H-1,2,4-triazol-4-yl)phenyl)-1,1-bis(methylthio) penta-1, 4-dien-3-one (6h) General procedure: To a solution of 1,1-dithiomethyl-1-en-3-butenone (5) (1.62 gm, 10 mmol) in methanol (40 ml), substituted benzaldehydes (4) (10 mmol) were added, followed by aqueous KOH solution (1.12 gm, 20 mmol, in 10 ml of water), the resulting reaction mixture was stirred at room temperature for 12 hr. It was concentrated in vacuo, poured into water (100 ml) and extracted with dichloromethane (50 ml x 3). The combined extract was washed with water (100 ml x 2), brine solution (50 ml x 2), and dried(Na2SO4). The solvent was removed in vacuo and the resulting crude product was column chromatographed (SiO2, 60-120 mesh). Elution with mixture of ethylacetate in hexane furnished compounds 6a-h.
  • 37
  • [ 17649-86-4 ]
  • 4,4-bis(methylthio)-3-bromo-but-3-en-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-Bromosuccinimide In dichloromethane at 20℃; for 1.5h; To a solution of 1,1-bis(methylthio)-but-1-en-3-one (2a) (1.0 equiv) in CH2Cl2 (5 mL/mmol) was added N-bromosuccinimide at 20 °C (1.2 equiv) and the solution was stirred for 1.5 h. Subsequently, 1,3-bis(trimethylsilyloxy)-1,3-butadiene 3 (2.0 equiv) and titanium tetrachloride (1.0 equiv) were added at -78 °C under argon atmosphere. The mixture was allowed to slowly warm to 20 °C and the mixture was stirred for 12 h. To the mixture was added hydrochloric acid (10%) and the organic layer was separated. Die aqueous layer was extracted with dichloromethane and the combined organic layers were dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography (silica gel, heptanes/EtOAc20:1).
  • 38
  • [ 17649-86-4 ]
  • [ 1443426-43-4 ]
YieldReaction ConditionsOperation in experiment
98% With N-chloro-succinimide In Carbon tetrachloride at 20℃; for 1.5h;
80% With N-chloro-succinimide In dichloromethane at 20℃; for 2h;
  • 39
  • [ 17649-86-4 ]
  • [ 81290-20-2 ]
  • 4,4-b is(methylthio)-3-(trifluoromethyl)but-3-en-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With potassium fluoride; 1,10-Phenanthroline; silver(I) carbonate; copper hydroxide In 1,2-dichloro-ethane at 100℃; for 24h; Inert atmosphere;
74% With potassium fluoride; [bis(acetoxy)iodo]benzene In acetonitrile at 20℃; for 0.5h; Sealed tube; Glovebox;
  • 40
  • [ 17649-86-4 ]
  • 4-(trifluoromethyl)-4-((trimethylsilyl)oxy)cyclohexa-2,5-dienone [ No CAS ]
  • methyl 3-hydroxy-2-(5-(methylthio)-2-(trifluoromethyl)phenyl)but-2-enethioate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With indium(III) triflate In 1,2-dichloro-ethane at 70℃; for 0.9h; regioselective reaction;
  • 41
  • [ 17649-86-4 ]
  • 4-(trifluoromethyl)-4-((trimethylsilyl)oxy)cyclohexa-2,5-dienone [ No CAS ]
  • [ 1493776-44-5 ]
YieldReaction ConditionsOperation in experiment
82% With indium(III) triflate; chloro-trimethyl-silane In 1,2-dichloro-ethane at 70℃; for 1.3h; regioselective reaction;
  • 42
  • [ 17649-86-4 ]
  • [ 1493776-61-6 ]
  • [ 1493776-51-4 ]
YieldReaction ConditionsOperation in experiment
80% With indium(III) triflate; chloro-trimethyl-silane In 1,2-dichloro-ethane at 70℃; for 1.4h; regioselective reaction;
  • 43
  • [ 17649-86-4 ]
  • [ 874-42-0 ]
  • [ 114577-52-5 ]
YieldReaction ConditionsOperation in experiment
99% With sodium hydroxide In ethanol at 10 - 20℃; for 0.5h;
99% With sodium hydroxide In ethanol at 0 - 20℃; for 0.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 44
  • [ 17649-86-4 ]
  • [ 587-04-2 ]
  • [ 1636155-19-5 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide In ethanol at 10 - 20℃; for 0.75h;
85% With sodium hydroxide In ethanol at 0 - 20℃; for 0.75h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 45
  • [ 17649-86-4 ]
  • [ 100-52-7 ]
  • [ 89812-50-0 ]
YieldReaction ConditionsOperation in experiment
81% With sodium hydroxide In ethanol at 10 - 20℃; for 0.75h;
81% With sodium hydroxide In ethanol at 0 - 20℃; for 0.75h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 46
  • [ 17649-86-4 ]
  • [ 1550-35-2 ]
  • [ 1636155-20-8 ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide In ethanol at 10 - 20℃; for 0.5h;
88% With sodium hydroxide In ethanol at 0 - 20℃; for 0.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 47
  • [ 17649-86-4 ]
  • [ 25016-01-7 ]
  • [ 1636155-21-9 ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide In ethanol at 10 - 20℃; for 0.666667h;
87% With sodium hydroxide In ethanol at 0 - 20℃; for 0.666667h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 48
  • [ 17649-86-4 ]
  • [ 446-52-6 ]
  • [ 1636155-23-1 ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide In ethanol at 10 - 20℃; for 0.75h;
92% With sodium hydroxide In ethanol at 0 - 20℃; for 0.75h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 49
  • [ 98-01-1 ]
  • [ 17649-86-4 ]
  • (E)-5-(furan-2-yl)-1,1-bis(methylthio)penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide In ethanol at 10 - 20℃; for 1.5h;
87% With sodium hydroxide In ethanol at 0 - 20℃; for 1.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 50
  • [ 98-03-3 ]
  • [ 17649-86-4 ]
  • (E)-1,1-bis(methylthio)-5-(thiophen-2-yl)-penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydroxide In ethanol at 10 - 20℃; for 1h;
86% With sodium hydroxide In ethanol at 0 - 20℃; for 1h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 51
  • [ 113118-81-3 ]
  • [ 17649-86-4 ]
  • [ 1636155-25-3 ]
YieldReaction ConditionsOperation in experiment
82% With sodium hydroxide In ethanol at 10 - 20℃; for 1h;
82% With sodium hydroxide In ethanol at 0 - 20℃; for 1h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 52
  • [ 603-76-9 ]
  • [ 17649-86-4 ]
  • [ 1160710-23-5 ]
YieldReaction ConditionsOperation in experiment
85% With indium(III) chloride In neat (no solvent) at 80℃; for 2h; Typical Procedure for Bis-indolyl Synthesis. General procedure: The α-oxoketenedithioacetal (2.0 mmol) and indole (4.0 mmol) were mixed throughly to get a paste like mixture. InCl3 (5 mol %)was added to the pasty mixture, which was then stirred at 80oC for the stipulated period of time. After completion of thereaction (as monitored by TLC), CH2Cl2 (10 mL) was addedto the mixture and then 20 mL of H2O was poured to the mixture. The organic layer was dried over anhydrous Na2S3and the solvent was evaporated under reduced pressure and purification by column chromatography over silica gel, elutingwith ethyl acetate-hexane (2:8, v/v), to give a yellow solid with 83% yield.
  • 53
  • [ 120-72-9 ]
  • [ 17649-86-4 ]
  • [ 1160710-39-3 ]
YieldReaction ConditionsOperation in experiment
73% With indium(III) chloride In neat (no solvent) at 80℃; for 2h; Typical Procedure for Bis-indolyl Synthesis. General procedure: The α-oxoketenedithioacetal (2.0 mmol) and indole (4.0 mmol) were mixed throughly to get a paste like mixture. InCl3 (5 mol %)was added to the pasty mixture, which was then stirred at 80oC for the stipulated period of time. After completion of thereaction (as monitored by TLC), CH2Cl2 (10 mL) was addedto the mixture and then 20 mL of H2O was poured to the mixture. The organic layer was dried over anhydrous Na2S3and the solvent was evaporated under reduced pressure and purification by column chromatography over silica gel, elutingwith ethyl acetate-hexane (2:8, v/v), to give a yellow solid with 83% yield.
  • 54
  • [ 17649-86-4 ]
  • [ 3759-28-2 ]
  • [ 1616775-92-8 ]
YieldReaction ConditionsOperation in experiment
63% With potassium hydroxide; In dimethyl sulfoxide; at 25 - 30℃; for 2h; General procedure: A mixture of 1-aryl/alkyl-3,3-bis-methylsulfanyl-propenone (1.0 mmol), <strong>[3759-28-2]2-cyanomethyl-benzonitrile</strong> (1 mmol, 142.0 mg), and powdered KOH (2 mmol, 112.0 mg) in dry DMSO (5 mL) was stirred at room temperature for 2 h. Completion of reaction was monitored by TLC. After completion, reaction mixture was poured onto ice-water with constant stirring and then neutralized with 10% HCl. The precipitate obtained was filtered, washed with water and dried over dry sodium sulfate. Many compounds were purified by recrystallization in dry methanol. Some compounds were purified through column chromatography using 15% ethylacetate in hexane as an eluent. Characterization data for some of the synthesized compounds are reported earlier.17
  • 55
  • [ 100-42-5 ]
  • [ 71098-88-9 ]
  • [ 17649-86-4 ]
  • 3-(bis(methylthio)methylene)-4-phenyl-5-(phenylselanyl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: N-phenylselanylphthalimide; 4,4-bis(methylthio)but-3-en-2-one With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h; Stage #2: styrene In 1,2-dichloro-ethane at 25℃; for 2h;
  • 56
  • [ 71098-88-9 ]
  • [ 17649-86-4 ]
  • [ 611-15-4 ]
  • 3-(bis(methylthio)methylene)-5-(phenylselanyl)-4-(o-tolyl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: N-phenylselanylphthalimide; 4,4-bis(methylthio)but-3-en-2-one With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h; Stage #2: 1-methyl-2-vinyl-benzene In 1,2-dichloro-ethane at 25℃; for 18h;
  • 57
  • [ 100-80-1 ]
  • [ 71098-88-9 ]
  • [ 17649-86-4 ]
  • 3-(bis(methylthio)methylene)-5-(phenylselanyl)-4-(m-tolyl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: N-phenylselanylphthalimide; 4,4-bis(methylthio)but-3-en-2-one With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h; Stage #2: 3-methylstyrene In 1,2-dichloro-ethane at 25℃; for 1h;
  • 58
  • [ 622-97-9 ]
  • [ 71098-88-9 ]
  • [ 17649-86-4 ]
  • 3-(bis(methylthio)methylene)-5-(phenylselanyl)-4-(p-tolyl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% Stage #1: N-phenylselanylphthalimide; 4,4-bis(methylthio)but-3-en-2-one With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h; Stage #2: 1-ethenyl-4-methylbenzene In 1,2-dichloro-ethane at 25℃; for 1h;
  • 59
  • [ 1073-67-2 ]
  • [ 71098-88-9 ]
  • [ 17649-86-4 ]
  • 3-(bis(methylthio)methylene)-4-(4-chlorophenyl)-5-(phenylselanyl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: N-phenylselanylphthalimide; 4,4-bis(methylthio)but-3-en-2-one With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h; Stage #2: 4-vinylbenzyl chloride In 1,2-dichloro-ethane at 25℃; for 2h;
  • 60
  • [ 71098-88-9 ]
  • [ 2039-82-9 ]
  • [ 17649-86-4 ]
  • 3-(bis(methylthio)methylene)-4-(4-bromophenyl)-5-(phenylselanyl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Stage #1: N-phenylselanylphthalimide; 4,4-bis(methylthio)but-3-en-2-one With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h; Stage #2: 1-bromo-4-ethenyl-benzene In 1,2-dichloro-ethane at 25℃; for 1.5h;
  • 61
  • [ 71098-88-9 ]
  • [ 17649-86-4 ]
  • [ 2350-89-2 ]
  • 4-([1,1'-biphenyl]-4-yl)-3-(bis(methylthio)methylene)-5-(phenylselanyl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: N-phenylselanylphthalimide; 4,4-bis(methylthio)but-3-en-2-one With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h; Stage #2: p-vinylbiphenyl In 1,2-dichloro-ethane at 25℃; for 1h;
  • 62
  • [ 71098-88-9 ]
  • [ 17649-86-4 ]
  • [ 1746-23-2 ]
  • 3-(bis(methylthio)methylene)-4-(4-(tert-butyl)phenyl)-5-(phenylselanyl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: N-phenylselanylphthalimide; 4,4-bis(methylthio)but-3-en-2-one With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h; Stage #2: 4-tert-Butylstyrene In 1,2-dichloro-ethane at 25℃; for 1h;
  • 63
  • [ 71098-88-9 ]
  • [ 17649-86-4 ]
  • [ 827-54-3 ]
  • 3-(bis(methylthio)methylene)-4-(naphthalen-2-yl)-5-(phenylselanyl)pentan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% Stage #1: N-phenylselanylphthalimide; 4,4-bis(methylthio)but-3-en-2-one With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h; Stage #2: 2-naphthylethylene In 1,2-dichloro-ethane at 25℃; for 4h;
  • 64
  • [ 17649-86-4 ]
  • [ 620-23-5 ]
  • (E)-1,1-bis(methylthio)-5-m-tolylpenta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydroxide In ethanol at 20℃; for 2h;
  • 65
  • [ 71098-88-9 ]
  • [ 17649-86-4 ]
  • 4,4-bis(methylthio)-3-(phenylselanyl)but-3-en-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 25℃; for 5h;
96% With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 30℃; for 5h; 1 In 25mL reaction tube were successively added p-TsOH · H2O (2.9mg, 0.015mmol), 3,3- dioxane-2- propen-1-one 2a (48.7mg, 0.30mmol), organic selenium reagents 3a (99.7mg, 0.33mmol) and 3mL solvent 1,2-dichloroethane, 30 reaction 5h. After completion of the reaction, volatile components were removed under reduced pressure, and then purified by silica gel column chromatography (eluent petroleum ether (60-90 / dichloromethane, v / v = 2: 1), to give a pale yellow solid target The product 1a (91.4mg, yield 96%).
  • 66
  • [ 17649-86-4 ]
  • [ 4559-70-0 ]
  • 3-(diphenylphosphoryl)-4,4-bis(methylthio)but-3-en-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With potassium 1,2-ethanedisulfonate In water; N,N-dimethyl-formamide at 80℃; for 5h;
  • 67
  • [ 17649-86-4 ]
  • [ 135-02-4 ]
  • (E)-5-(2-methoxyphenyl)-1,1-bis(methylthio)-penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide In ethanol at 0 - 20℃; for 0.333333h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 68
  • [ 17649-86-4 ]
  • [ 591-31-1 ]
  • [ 114577-54-7 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide In ethanol at 0 - 20℃; for 1.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 69
  • [ 17649-86-4 ]
  • [ 456-48-4 ]
  • (E)-5-(3-fluorophenyl)-1,1-bis(methylthio)-penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydroxide In ethanol at 0 - 20℃; for 0.833333h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 70
  • [ 17649-86-4 ]
  • [ 6630-33-7 ]
  • (E)-5-(2-bromophenyl)-1,1-bis(methylthio)-penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With sodium hydroxide In ethanol at 0 - 20℃; for 0.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 71
  • [ 17649-86-4 ]
  • [ 1122-91-4 ]
  • (E)-5-(4-b romophenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydroxide In ethanol at 0 - 20℃; for 0.666667h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 72
  • [ 17649-86-4 ]
  • [ 105-07-7 ]
  • (E)-4-(5,5-bis(methylthio)-3-oxopenta-1,4-dien-1-yl)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide In ethanol at 0 - 20℃; for 1.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 73
  • [ 17649-86-4 ]
  • [ 77771-02-9 ]
  • (E)-5-(3-bromo-4-fluorophenyl)-1,1-bis(methylthio)-penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% With sodium hydroxide; In ethanol; at 0 - 20℃; for 0.75h; General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 74
  • [ 17649-86-4 ]
  • [ 6361-21-3 ]
  • (E)-5-(2-chloro-5-nitrophenyl)-1,1-bis(methylthio)penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With sodium hydroxide In ethanol at 0 - 20℃; for 1.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 75
  • [ 17649-86-4 ]
  • [ 66-77-3 ]
  • (E)-1,1-bis(methylthio)-5-(naphthalene-1-yl)penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide In ethanol at 0 - 20℃; for 1.66667h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 76
  • [ 17649-86-4 ]
  • [ 642-31-9 ]
  • (E)-5-(anthra-cen-9-yl)-1,1-bis(methylthio)penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With sodium hydroxide In ethanol at 0 - 20℃; for 1.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 77
  • [ 17649-86-4 ]
  • [ 3029-19-4 ]
  • (E)-1,1-bis(methylthio)-5-(pyren-1-yl)penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With sodium hydroxide In ethanol at 0 - 20℃; for 1.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 78
  • [ 4701-17-1 ]
  • [ 17649-86-4 ]
  • (E)-5-(5-bromothiophen-2-yl)-1,1-bis(methylthio)-penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With sodium hydroxide In ethanol at 0 - 20℃; for 1.5h; General procedure for the synthesis of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one (2a-y) General procedure: To a solution of 4,4-bis(methylthio)but-3-en-2-one (1mol) in ethanol (10 ml) were added NaOH (1.5mol) and aryl aldehyde (1.1 mol) under constant stirring. After the starting material was consumed as indicated by TLC, the reaction mixture was poured into ice water and the resulting solid was filtered, washed well with water (20 ml). The solid material obtained was crystallized from ethanol to furnish 81-99% of 1,1-bis(methylthio)-5-arylpenta-1,4-dien-3-one as a yellow solid.
  • 79
  • [ 61-54-1 ]
  • [ 17649-86-4 ]
  • C14H14N2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
89% Stage #1: tryptamine; 4,4-bis(methylthio)but-3-en-2-one With indium(III) chloride In acetonitrile for 2h; Reflux; Stage #2: With trifluoroacetic acid In acetonitrile Reflux; 2.2 General procedure for the synthesis of 1-(substituted)methylene-1,2,3,4-tetrahydro-β-carbolines (5a-l) General procedure: To a solution of the ketene S,S-acetal (3 mmol) and tryptamine (3 mmol) in CH3CN (15 mL), InCl3 (2 mol%) was added and refluxed. After refluxing for 2 h, TFA (15 mol %) was added to the reaction mixture and refluxing was continued for 1-2 h (monitored by TLC).Then, the reaction mixture was poured into ice-cold water and extracted with CH2Cl2 (30 mL). The combined organic layer was washed with H2O (25 mL),dried (Na2SO4) and the solvent was evaporated under reduced pressure to afford the crude product whic hwas purified by column chromatography over silica gel using hexane-EtOAc (8:2) as eluent.
  • 80
  • [ 17649-86-4 ]
  • C6H9FOS2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
61% With Selectfluor In acetonitrile at 20℃; for 4h; General method for the preparation of α-fluoro-α-oxoketenedithioacetals. Route 1 3a-l General procedure: To a well stirred solution of selectfluor (0.797 g, 2.25 mmol) in MeCN (8 ml) at 0 °C, a solution of 1 (0.336 g, 1.5 mmol) in MeCN (5 ml) was added drop wise and stirring was continued at room temperature for 3-6 h (Monitored by TLC). The reaction mixture was poured into ice cold water and extracted with 30 ml of ethyl acetate. The ethyl acetate extract was dried with sodium sulfate and evaporated under vacuum to give crude α-fluoro-α-oxoketenedithioacetals 3 which were further purified through a silica gel column using petroleum ether and ethyl acetate (9:1) as eluent.
  • 81
  • [ 5707-04-0 ]
  • [ 17649-86-4 ]
  • 4,4-bis(methylthio)-3-(phenylselanyl)but-3-en-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
50% With toluene-4-sulfonic acid In 1,2-dichloro-ethane at 30℃; for 5h; 2 In 25mL reaction tube were successively added p-TsOH · H2O (2.9mg, 0.015mmol), 3,3- dioxane-2- propen-1-one 2a (48.7mg, 0.30mmol), organic selenium reagents 3a (99.7mg, 0.33mmol) and 3mL solvent 1,2-dichloroethane, 30 reaction 5h. After completion of the reaction, volatile components were removed under reduced pressure, and then purified by silica gel column chromatography (eluent petroleum ether (60-90 / dichloromethane, v / v = 2: 1), to give a pale yellow solid target. The reaction procedure as in Example 1 with the operation of Example 1 except that the organic reagent is selenium 3b phenylselenyl chloride (63.2mg, 0.33mmol). The reaction was stopped after treatment to give the desired product 1a (47.6mg, 50% yield).
  • 82
  • [ 12093-10-6 ]
  • [ 17649-86-4 ]
  • 5-ferrocenyl-1,1-bis(methylthio)penta-1,4-dien-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Stage #1: 4,4-bis(methylthio)but-3-en-2-one With ethanol; sodium at 0℃; for 0.0833333h; Stage #2: ferrocenecarboxaldehyde at 0 - 20℃; for 12h; 5-Ferrocenyl-1,1-bis(methylthio)penta-1,4-dien-3-one (10) Ketene dithioacetal 9 (1.0 mmol) was added to a stirred solution of NaOEt [4 mmol, prepared in situ from Na (0.09 g) and EtOH (3 mL)] in EtOH (10 mL) at 0 °C. After 5 min, ferrocenecarbaldehyde (8, 1.1 mmol) was added and the mixture was stirred for 12 h at r.t. (monitored by TLC), the solvent was evaporated under reduced pressure and the residue was treated with ice-cold water (20 mL). It was then extracted with CHCl3 (3 × 30 mL). The combined organic extracts were washed with water (3 × 40 mL) and brine (1 × 30 mL) and dried (anhyd Na2SO4). The solvent was evaporated under reduced pressure and the crude product was purified by column chromatography (neutral alumina) to give the product as a pink solid; yield: 0.22 g (60%); mp 144-146 °C; Rf = 0.5 (hexane/EtOAc, 9:1). FTIR (KBr): 3094, 2917, 1641, 1585, 1487, 1126 cm-1. 1H NMR (400 MHz, CDCl3): δ = 7.49 (d, J = 15.3 Hz, 1 H, vinylic-H), 6.41 (d, J = 15.3 Hz, 1 H, vinylic-H), 6.11 (s, 1 H, vinylic-H), 4.49 (s, 2 H, Fc-H), 4.39 (s, 2 H, Fc-H), 4.12 (s, 5 H, Fc-H), 2.48 (s, 6 H, SMe). 13C NMR (100 MHz, CDCl3): δ = 183.5, 163.7, 142.4, 124.5, 113.5, 79.5, 70.7, 69.5, 68.5, 17.1, 14.9. Anal. Calcd for C17H18FeOS2: C, 56.99; H, 5.06. Found: C, 56.97; H, 5.09.
  • 83
  • [ 17649-86-4 ]
  • [ 24922-02-9 ]
  • ethyl 4-acetyl-2-cyclopropyl-5-(methylthio)furan-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% With tert-Butyl peroxybenzoate; iron(II) acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere; regioselective reaction;
  • 84
  • [ 17649-86-4 ]
  • [ 94-02-0 ]
  • ethyl 4-acetyl-5-(methylthio)-2-phenylfuran-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% With tert-Butyl peroxybenzoate; iron(II) acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere; regioselective reaction;
  • 85
  • [ 17649-86-4 ]
  • [ 372-31-6 ]
  • ethyl 4-acetyl-5-(methylthio)-2-(trifluoromethyl)furan-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
74% With tert-Butyl peroxybenzoate; iron(II) acetate In N,N-dimethyl acetamide at 120℃; for 20h; Inert atmosphere; regioselective reaction;
Same Skeleton Products
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