[ CAS No. 42248-31-7 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 42248-31-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 42248-31-7 ]

Product Details of [ 42248-31-7 ]

CAS No. :	42248-31-7	MDL No. :	MFCD00139138
Formula :	C₁₀H₅ClO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LIGLNCRTMDRUAO-UHFFFAOYSA-N
M.W :	208.60	Pubchem ID :	463777
Synonyms :

Safety of [ 42248-31-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 42248-31-7 ]

* 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 [ 42248-31-7 ]

[ 42248-31-7 ] Synthesis Path-Downstream 1~50

1
[ 1004-40-6 ]
[ 42248-31-7 ]
[ 84668-98-4 ]

Reference： [1]Archiv der Pharmazie,1983,vol. 316,p. 55 - 62

2
[ 42248-31-7 ]
[ 41939-61-1 ]
6-Chloro-3-[(Z)-2-methylamino-5-nitro-phenylimino]-methyl}-chromen-4-one [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1988,vol. 65,p. 567 - 570

3
[ 42248-31-7 ]
[ 41939-61-1 ]
9-Chloro-5-methyl-2-nitro-5a,13-dihydro-5H-6-oxa-5,13-diaza-benzo[4,5]cyclohepta[1,2-b]naphthalen-11-one [ No CAS ]

Reference： [1]Journal of the Indian Chemical Society,1988,vol. 65,p. 567 - 570

4
[ 42248-31-7 ]
[ 66108-86-9 ]
3-[(Z)-2-Benzylamino-5-nitro-phenylimino]-methyl}-6-chloro-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In acetic acid Heating;

Reference： [1]Devi; Achaiah; Malla Reddy [Journal of the Indian Chemical Society, 1988, vol. 65, # 8, p. 567 - 570]

5
[ 42248-31-7 ]
[ 66108-86-9 ]
5-Benzyl-9-chloro-2-nitro-5a,13-dihydro-5H-6-oxa-5,13-diaza-benzo[4,5]cyclohepta[1,2-b]naphthalen-11-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With toluene-4-sulfonic acid In benzene for 2h; Heating;

Reference： [1]Devi; Achaiah; Malla Reddy [Journal of the Indian Chemical Society, 1988, vol. 65, # 8, p. 567 - 570]

6
[ 64-17-5 ]
[ 570-23-0 ]
[ 42248-31-7 ]
3-(3-carboxy-2-hydroxyphenyl)aminomethylene-6-chloro-2-ethoxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With toluene-4-sulfonic acid for 2h; Ambient temperature;
73%	With toluene-4-sulfonic acid at 20℃; for 12h;
	With toluene-4-sulfonic acid at 40.5℃;

Reference： [1]Lacova; Stankovicova; Odlerova [Il Farmaco, 1995, vol. 50, # 12, p. 885 - 888]
[2]Stankovičová, Henrieta; Lácová, Margita; Gáplovský, Anton; Chovancová, Jarmila; Prónayová, Nad'A [Tetrahedron, 2001, vol. 57, # 16, p. 3455 - 3464]
[3]Stankovičová, Henrieta; Lácová, Margita; Gáplovský, Anton; Chovancová, Jarmila; Prónayová, Nad'A [Tetrahedron, 2001, vol. 57, # 16, p. 3455 - 3464]

7
[ 37674-72-9 ]
[ 42248-31-7 ]
6-Chloro-3-[6-chloro-4-oxo-chroman-(3Z)-ylidenemethyl]-chromen-4-one [ No CAS ]

Reference： [1]Organic Preparations and Procedures International,1996,vol. 28,p. 325 - 332

8
[ 5782-85-4 ]
[ 42248-31-7 ]
3,4,5-Trihydroxy-benzoic acid [1-(6-chloro-4-oxo-4H-chromen-3-yl)-meth-(E)-ylidene]-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid In ethanol
	With toluene-4-sulfonic acid In ethanol at 60℃; for 1h; Yield given;

Reference： [1]Foltinova, Pavlina; Lacova, Margita; Loos, Dusan [Il Farmaco, 2000, vol. 55, # 1, p. 21 - 26]
[2]El-Shaaer, Hafez M.; Foltinova, Pavlina; Lacova, Margita; Chovancova, Jarmila; Stankovicova, Henrieta [Il Farmaco, 1998, vol. 53, # 3, p. 224 - 232]

9
[ 112393-45-0 ]
[ 42248-31-7 ]
6-Chloro-3-[(E)-2-(4-chloro-benzenesulfonyl)-3-(4-chloro-phenyl)-3-oxo-propenyl]-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20%	With benzylamine In acetic anhydride for 8h; Heating;

Reference： [1]Naidu, M. S. R.; Naidu, R. Ravi [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1997, vol. 36, # 1, p. 99 - 100]

10
[ 60-27-5 ]
[ 541-41-3 ]
[ 42248-31-7 ]
[5-(6-chloro-4-oxo-4H-chromen-3-ylmethylene)-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl]-carbamic acid [ No CAS ]

Reference： [1]Molecules,2000,vol. 5,p. 167 - 178

11
[ 60-27-5 ]
[ 108-24-7 ]
[ 42248-31-7 ]
N-[5-(6-chloro-4-oxo-4H-chromen-3-ylmethylene)-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl]-acetamide [ No CAS ]

Reference： [1]Molecules,2000,vol. 5,p. 167 - 178

12
[ 60-27-5 ]
[ 42248-31-7 ]
5-[1-(6-Chloro-4-oxo-4H-chromen-3-yl)-meth-(Z)-ylidene]-2-imino-1-methyl-imidazolidin-4-one [ No CAS ]

Reference： [1]Molecules,2000,vol. 5,p. 167 - 178

13
[ 570-23-0 ]
[ 42248-31-7 ]
3-(3-carboxy-2-hydroxyphenyl)aminomethylene-6-chloro-2-hydroxychroman-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With toluene-4-sulfonic acid for 3h; Heating;

Reference： [1]Stankovičová, Henrieta; Lácová, Margita; Gáplovský, Anton; Chovancová, Jarmila; Prónayová, Nad'A [Tetrahedron, 2001, vol. 57, # 16, p. 3455 - 3464]

14
[ 42248-31-7 ]
[ 51347-93-4 ]
[ 293738-33-7 ]

Yield	Reaction Conditions	Operation in experiment
84%	In chloroform at 20℃; for 3h;

Reference： [1]Reddy, G. Jagath; Latha; Thirupathaiah [Heterocyclic Communications, 2003, vol. 9, # 3, p. 243 - 246]

15
[ 42248-31-7 ]
[ 4865-84-3 ]
3-(2-benzo[d]isoxazol-3-yl-vinyl)-6-chloro-chromen-4-one [ No CAS ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2006,vol. 45,p. 288 - 291

16
[ 42248-31-7 ]
[ 168837-89-6 ]
2-methyl-4H-furo[3,2-b]pyrrole-5-carboxylic acid (6-chloro-4-oxo-4H-chromen-3-ylmethylene)-hydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With toluene-4-sulfonic acid In ethanol for 0.0833333h; microwave irradiation;

Reference： [1]Gasparova, Renata; Lacova, Margita; Krutosikova, Alzbeta [Collection of Czechoslovak Chemical Communications, 2005, vol. 70, # 12, p. 2101 - 2111]

17
[ 65235-90-7 ]
[ 42248-31-7 ]
[ 42059-70-1 ]
[ 1263273-24-0 ]
[ 1263273-34-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 60% 2: 17% 3: 5%	With pyridine In tetrahydrofuran at 50 - 60℃; for 2h;	2. General procedure for pyranochromene-3-carboxamides 11a-h, pyranothiazine-4,7-diones 12a-h and (2E)-3-(4-oxo-4H-chromen-3-yl)prop-2-enoic acids 13a-g 2-Aryl-4-hydroxy-6H-1,3-thiazin-6-one 7 (0.01 mol) was dissolved in 20 ml of THF, then 1 ml of pyridine was added. The solution was heated to 50 °C and the respective 3-formylchromone 1 was added (0.011 mol). Heating was continued at 50-60 °C for 2 h with intermittent stirring. The solvent was removed in vacuo (20 mmHg), EtOH (10 ml) was added to the residue, and the formed precipitate filtered, washed with EtOH (3 × 10 ml), and recrystallized from THF to give pyranochromenes 11 as brownish-orange powder. The ethanolic rinses were evaporated under a current of air to a volume of 5 ml. CH2Cl2 (20 ml) was added, the formed precipitate filtered, washed with CH2Cl2 (3 × 10 ml), and recrystallized from EtOH to give propenoic acids 13 as yellowish powders. The CH2Cl2 rinses were evaporated under a current of air to a volume of 5 ml and n-hexane (20 ml) was added. The formed precipitate was filtered, washed with n-hexane (3 × 10 ml), and recrystallized from CH2Cl2-C6H14 (1:1) to give pyranothiazines 12 as yellow powders.

Reference： [1]Location in patent: experimental part Shutov, Roman V.; Kuklina, Elizaveta V.; Ivin, Boris A. [Tetrahedron Letters, 2011, vol. 52, # 2, p. 266 - 269]

18
[ 14542-93-9 ]
[ 42248-31-7 ]
(1Z)-7-chloro-1-[(6-chloro-4-oxo-4H-chromen-3-yl)methylene]-3-[(1,1,3,3-tetramethylbutyl)imino]-1,3-dihydro-9H-furo[3,4-b]chromen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In dichloromethane at 25℃; for 96h; stereoselective reaction;	2.2. Typical procedure for preparation of (1Z)-1-[(4-oxo-4H-chromen-3-yl)methylene]-3-[(1,1,3,3-tetramethylbutyl)imino]-1,3-dihydro-9H-furo[3,4-b]chromen-9-one (3a) General procedure: To a magnetically stirred solution of 3-formylchromone (0.348 g, 2.0 mmol) in dry CH2Cl2 (10 mL) in a screw-capped vial, was added tert-octyl isocyanide (0.140 g, 1.0 mmol) via a syringe at room temperature (25 °C). The reaction mixture was then stirred for 4 days and the completion of reaction was confirmed by TLC (EtOAc/hexane 1:1). Then, the resulting solids were filtered and washed with acetone (5 mL) to yield 3a as a yellow powder (0.390 g, 83%). The dried product thus obtained showed a single spot on TLC and was pure enough for all analytical purposes.

Reference： [1]Location in patent: experimental part Teimouri, Mohammad Bagher [Tetrahedron, 2011, vol. 67, # 10, p. 1837 - 1843]

19
[ 119-65-3 ]
[ 99-81-0 ]
[ 42248-31-7 ]
[ 1286733-59-2 ]

Yield	Reaction Conditions	Operation in experiment
94%	With cetyltrimethylammonim bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 20℃; for 1h;	General reaction procedure for the synthesis of pyrrolo[2,1-a]isoquinolines: One mmol each of the isoquinoline (1a-b), phenacyl bromide/bromoacetic acid ester (2a-j), and chromone-3-carboxaldehyde (3a-c) derivatives were taken in a 100 ml RB flask. Then water (50 ml), CTAB (4 mmol) and DBU (1 mmol) were added and the mixture was stirred continuously for 1 h at room temperature. After completion of the reaction (monitored by TLC), the contents of the reaction mixture were poured into a separating funnel and extracted with ethyl acetate (3 × 25 ml). The organic layer was washed thoroughly with water until free from CTAB and base, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over a column of silica gel (60-120 mesh) eluting with a mixture of hexane and ethyl acetate in different ratios, to yield the pyrrolo[2,1-a]isoquinolines (4a-x).

Reference： [1]Naskar, Subhendu; Banerjee, Maitreyee; Hazra, Abhijit; Mondal, Shyamal; Maity, Arindam; Paira, Rupankar; Sahu, Krishnendu B.; Saha, Pritam; Banerjee, Sukdeb; Mondal, Nirup B. [Tetrahedron Letters, 2011, vol. 52, # 13, p. 1527 - 1531]

20
[ 119-65-3 ]
[ 42248-31-7 ]
[ 105-36-2 ]
[ 1286733-73-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cetyltrimethylammonim bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 20℃; for 1h;	General reaction procedure for the synthesis of pyrrolo[2,1-a]isoquinolines: One mmol each of the isoquinoline (1a-b), phenacyl bromide/bromoacetic acid ester (2a-j), and chromone-3-carboxaldehyde (3a-c) derivatives were taken in a 100 ml RB flask. Then water (50 ml), CTAB (4 mmol) and DBU (1 mmol) were added and the mixture was stirred continuously for 1 h at room temperature. After completion of the reaction (monitored by TLC), the contents of the reaction mixture were poured into a separating funnel and extracted with ethyl acetate (3 × 25 ml). The organic layer was washed thoroughly with water until free from CTAB and base, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over a column of silica gel (60-120 mesh) eluting with a mixture of hexane and ethyl acetate in different ratios, to yield the pyrrolo[2,1-a]isoquinolines (4a-x).

21
[ 119-65-3 ]
[ 42248-31-7 ]
[ 2632-10-2 ]
[ 1286733-67-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cetyltrimethylammonim bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In water; at 20℃; for 1h;	One mmol each of the isoquinoline (1a-b), phenacyl bromide/bromoacetic acid ester (2a-j), and chromone-3-carboxaldehyde (3a-c) derivatives were taken in a 100 ml RB flask. Then water (50 ml), CTAB (4 mmol) and DBU (1 mmol) were added and the mixture was stirred continuously for 1 h at room temperature. After completion of the reaction (monitored by TLC), the contents of the reaction mixture were poured into a separating funnel and extracted with ethyl acetate (3 × 25 ml). The organic layer was washed thoroughly with water until free from CTAB and base, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over a column of silica gel (60-120 mesh) eluting with a mixture of hexane and ethyl acetate in different ratios, to yield the pyrrolo[2,1-a]isoquinolines (4a-x).

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1527 - 1531

22
[ 119-65-3 ]
[ 42248-31-7 ]
[ 135-73-9 ]
[ 1286733-65-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cetyltrimethylammonim bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 20℃; for 1h;	General reaction procedure for the synthesis of pyrrolo[2,1-a]isoquinolines: One mmol each of the isoquinoline (1a-b), phenacyl bromide/bromoacetic acid ester (2a-j), and chromone-3-carboxaldehyde (3a-c) derivatives were taken in a 100 ml RB flask. Then water (50 ml), CTAB (4 mmol) and DBU (1 mmol) were added and the mixture was stirred continuously for 1 h at room temperature. After completion of the reaction (monitored by TLC), the contents of the reaction mixture were poured into a separating funnel and extracted with ethyl acetate (3 × 25 ml). The organic layer was washed thoroughly with water until free from CTAB and base, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over a column of silica gel (60-120 mesh) eluting with a mixture of hexane and ethyl acetate in different ratios, to yield the pyrrolo[2,1-a]isoquinolines (4a-x).

23
[ 119-65-3 ]
[ 42248-31-7 ]
[ 70-11-1 ]
[ 1286733-53-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With cetyltrimethylammonim bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 20℃; for 1h;	General reaction procedure for the synthesis of pyrrolo[2,1-a]isoquinolines: One mmol each of the isoquinoline (1a-b), phenacyl bromide/bromoacetic acid ester (2a-j), and chromone-3-carboxaldehyde (3a-c) derivatives were taken in a 100 ml RB flask. Then water (50 ml), CTAB (4 mmol) and DBU (1 mmol) were added and the mixture was stirred continuously for 1 h at room temperature. After completion of the reaction (monitored by TLC), the contents of the reaction mixture were poured into a separating funnel and extracted with ethyl acetate (3 × 25 ml). The organic layer was washed thoroughly with water until free from CTAB and base, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over a column of silica gel (60-120 mesh) eluting with a mixture of hexane and ethyl acetate in different ratios, to yield the pyrrolo[2,1-a]isoquinolines (4a-x).

24
[ 119-65-3 ]
[ 42248-31-7 ]
[ 619-41-0 ]
[ 1286733-62-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With cetyltrimethylammonim bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 20℃; for 1h;	General reaction procedure for the synthesis of pyrrolo[2,1-a]isoquinolines: One mmol each of the isoquinoline (1a-b), phenacyl bromide/bromoacetic acid ester (2a-j), and chromone-3-carboxaldehyde (3a-c) derivatives were taken in a 100 ml RB flask. Then water (50 ml), CTAB (4 mmol) and DBU (1 mmol) were added and the mixture was stirred continuously for 1 h at room temperature. After completion of the reaction (monitored by TLC), the contents of the reaction mixture were poured into a separating funnel and extracted with ethyl acetate (3 × 25 ml). The organic layer was washed thoroughly with water until free from CTAB and base, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over a column of silica gel (60-120 mesh) eluting with a mixture of hexane and ethyl acetate in different ratios, to yield the pyrrolo[2,1-a]isoquinolines (4a-x).

25
[ 119-65-3 ]
[ 42248-31-7 ]
[ 403-29-2 ]
[ 1286733-56-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With cetyltrimethylammonim bromide; 1,8-diazabicyclo[5.4.0]undec-7-ene In water at 20℃; for 1h;	General reaction procedure for the synthesis of pyrrolo[2,1-a]isoquinolines: One mmol each of the isoquinoline (1a-b), phenacyl bromide/bromoacetic acid ester (2a-j), and chromone-3-carboxaldehyde (3a-c) derivatives were taken in a 100 ml RB flask. Then water (50 ml), CTAB (4 mmol) and DBU (1 mmol) were added and the mixture was stirred continuously for 1 h at room temperature. After completion of the reaction (monitored by TLC), the contents of the reaction mixture were poured into a separating funnel and extracted with ethyl acetate (3 × 25 ml). The organic layer was washed thoroughly with water until free from CTAB and base, dried over sodium sulfate, and evaporated to dryness in a rotary evaporator under reduced pressure. The residue was chromatographed over a column of silica gel (60-120 mesh) eluting with a mixture of hexane and ethyl acetate in different ratios, to yield the pyrrolo[2,1-a]isoquinolines (4a-x).

26
[ 2555-37-5 ]
[ 42248-31-7 ]
[ 1316841-05-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With zinc(II) L-prolinate complex In water for 0.25h; Reflux;	General method for the preparation of chromonyl chalcones (3a-o) General procedure: To a partially suspended Zn(l-Proline)2 (10 mol %) in water (10 mL), 3-formylchromones (1a-c) (4 mmol) and heteroaryl active methyl compounds (2a-e) (4 mmol) were added successively and heated under reflux condition for appropriate time (Table 1). After the completion of reaction, as monitored by TLC, the product was extracted with dichloromethane (3 × 15 mL) until complete removal of organic component, dried over anhydrous Na2SO4, concentrated to furnish crude product, which was then recrystallized from chloroform or methanol-DMF mixture. The catalyst was recovered by precipitating the aqueous layer by addition of acetone. The catalyst recovered from the aqueous layer was used for the subsequent cycle.Table 1). After the completion of reaction, as monitored by TLC, the product was extracted with dichloromethane (3 × 15 mL) until complete removal of organic component, dried over anhydrous Na2SO4, concentrated to furnish crude product, which was then recrystallized from chloroform or methanol-DMF mixture. The catalyst was recovered by precipitating the aqueous layer by addition of acetone. The catalyst recovered from the aqueous layer was used for the subsequent cycle.

Reference： [1]Location in patent: experimental part Siddiqui, Zeba N.; Musthafa, T.N. Mohammed [Tetrahedron Letters, 2011, vol. 52, # 31, p. 4008 - 4013]

27
[ 141-82-2 ]
[ 42248-31-7 ]
[ 42059-70-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	With aluminum potassium sulfate dodecahydrate for 0.0916667h; Microwave irradiation;
82%	With pyridine for 0.75h; Reflux;

Reference： [1]Location in patent: experimental part Suresh, Dhruva Kumar; Sandhu, Jagir S. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 10, p. 1479 - 1483]
[2]Gao, Yuqi; Guo, Lei; Huang, Yi-You; Lai, Zengwei; Li, Xiangmin; Li, Zhe; Luo, Hai-Bin; Wu, Deyan; Wu, Yinuo; Yu, Yan-Fa; Zhang, Chen; Zhang, Sirui; Zhou, Qian [ACS Chemical Neuroscience, 2020]

28
[ 40928-13-0 ]
[ 104-94-9 ]
[ 42248-31-7 ]
C₂₄H₁₆Cl₂N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%		General procedure: Typical procedure for the preparation of benzochromenodiazocines 4: A mixture of isatoic anhydride (1 mmol) and NH4OAc (1.5 mmol) or an amine (1 mmol) was stirred in refluxing toluene (5 mL) for 1 h. 3-Formylchromone 1 (1 mmol) was added and the mixture was stirred at reflux for 4 h. After completion of the reaction, the mixture was filtered and the precipitate washed with EtOH to afford the pure product 4. 13a,14-dihydro-5H-benzo[g]chromeno[2,3-b][1,5]diazocine-5,8(6H)-dione (4a): Light yellow powder (0.25 g, 87%). Mp 169-171 C; IR (KBr) (numax/cm-1): 3410, 3304, 1652, 1608. 1H NMR (300 MHz, DMSO-d6): deltaH 6.85 (1H, s, CH), 7.07-7.16 (3H, m, Ar-H), 7.49-7.84 (5H, m, Ar-H), 8.01 (1H, d, J = 12.9 Hz, =CH), 8.13 (1H, br s, NH), 13.01 (1H, d, J = 12.9 Hz, NHCO). 13C NMR (75 MHz, DMSO-d6): deltaC 54.8, 101.8, 104.6, 114.8, 117.5, 121.4, 122.2, 122.7, 125.9, 128.9, 132.0, 133.7, 140.1, 141.8, 155.4, 169.3, 179.5. MS (EI, 70 eV) m/z: 291 (M+-1). Anal. Calcd for C17H12N2O3: C, 69.86; H, 4.14; N, 9.58. Found: C, 69.74; H, 4.07; N, 9.50. 6-Methyl-13a,14-dihydro-5H-benzo[g]chromeno[2,3-b][1,5]diazocine-5,8(6H)-dione (4b): White powder (0.29 g, 95%). Mp 214-216 C; IR (KBr) (numax/cm-1): 3315, 1633, 1606. 1H NMR (300 MHz, DMSO-d6): deltaH 2.96 (3H, s, CH3), 6.49 (1H, s, CH), 6.65-6.74 (2H, m, Ar-H), 6.97 (1H, br s, NH), 7.16-7.84 (5H, m, Ar-H), 8.03 (1H, s, =CH), 8.09 (1H, d, J = 7.9 Hz, Ar-H). 13C NMR (75 MHz, DMSO-d6): deltaC 32.6, 66.3, 114.7, 115.0, 118.1, 119.0, 121.0, 123.5, 125.4, 126.4, 127.8, 133.9, 135.2, 146.3, 153.9, 156.2, 164.5, 176.7. Anal. Calcd for C18H14N2O3: C, 70.58; H, 4.61; N, 9.15. Found: C, 70.69; H, 4.56; N, 9.08.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1960 - 1962

29
[ 40928-13-0 ]
[ 42248-31-7 ]
[ 62-53-3 ]
C₂₃H₁₄Cl₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%		General procedure: Typical procedure for the preparation of benzochromenodiazocines 4: A mixture of isatoic anhydride (1 mmol) and NH4OAc (1.5 mmol) or an amine (1 mmol) was stirred in refluxing toluene (5 mL) for 1 h. 3-Formylchromone 1 (1 mmol) was added and the mixture was stirred at reflux for 4 h. After completion of the reaction, the mixture was filtered and the precipitate washed with EtOH to afford the pure product 4. 13a,14-dihydro-5H-benzo[g]chromeno[2,3-b][1,5]diazocine-5,8(6H)-dione (4a): Light yellow powder (0.25 g, 87%). Mp 169-171 C; IR (KBr) (numax/cm-1): 3410, 3304, 1652, 1608. 1H NMR (300 MHz, DMSO-d6): deltaH 6.85 (1H, s, CH), 7.07-7.16 (3H, m, Ar-H), 7.49-7.84 (5H, m, Ar-H), 8.01 (1H, d, J = 12.9 Hz, =CH), 8.13 (1H, br s, NH), 13.01 (1H, d, J = 12.9 Hz, NHCO). 13C NMR (75 MHz, DMSO-d6): deltaC 54.8, 101.8, 104.6, 114.8, 117.5, 121.4, 122.2, 122.7, 125.9, 128.9, 132.0, 133.7, 140.1, 141.8, 155.4, 169.3, 179.5. MS (EI, 70 eV) m/z: 291 (M+-1). Anal. Calcd for C17H12N2O3: C, 69.86; H, 4.14; N, 9.58. Found: C, 69.74; H, 4.07; N, 9.50. 6-Methyl-13a,14-dihydro-5H-benzo[g]chromeno[2,3-b][1,5]diazocine-5,8(6H)-dione (4b): White powder (0.29 g, 95%). Mp 214-216 C; IR (KBr) (numax/cm-1): 3315, 1633, 1606. 1H NMR (300 MHz, DMSO-d6): deltaH 2.96 (3H, s, CH3), 6.49 (1H, s, CH), 6.65-6.74 (2H, m, Ar-H), 6.97 (1H, br s, NH), 7.16-7.84 (5H, m, Ar-H), 8.03 (1H, s, =CH), 8.09 (1H, d, J = 7.9 Hz, Ar-H). 13C NMR (75 MHz, DMSO-d6): deltaC 32.6, 66.3, 114.7, 115.0, 118.1, 119.0, 121.0, 123.5, 125.4, 126.4, 127.8, 133.9, 135.2, 146.3, 153.9, 156.2, 164.5, 176.7. Anal. Calcd for C18H14N2O3: C, 70.58; H, 4.61; N, 9.15. Found: C, 70.69; H, 4.56; N, 9.08.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1960 - 1962

30
[ 39115-96-3 ]
[ 42248-31-7 ]
[ 351470-23-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With acetic acid; In ethanol; at 20℃; for 6h;	General procedure: to a mixture solution of 3-formylchromone d1 (174 mg, 1 mmol) and benzohydrazide e1 (136 mg, 1 mmol) in 25 mL ethanol was added three drops of acetic acid with stirring for 6 h at room temperature. Insoluble solid was gradually generated, then filtered and washed several times with ethanol. After drying, pure target compound f1 was afforded (227 mg, yield 78%).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 2826 - 2831

31
[ 73870-25-4 ]
[ 42248-31-7 ]
[ 1550910-08-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	Stage #1: (pyridin-4-ylmethyl)triphenylphosphonium chloride With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: 6-Chloro-4-oxo-4H-chromene-3-carbaldehyde In tetrahydrofuran at 20℃; for 20h;	General procedure for the synthesis of [2-(2H-chromen-3-yl)vinyl]pyridines (5a, 5b, 6a, 6b, 7a, 7b, 8a, 9a) and 3-[2-(pyridinyl)vinyl]-4H-chromen-4-ones (11a, 11b, 12a, 12b, 13a, 13b) General procedure: Potassium tert-butoxide (20 mmol) was added to a stirred suspension of the appropriate pyridilmethyltriphenylphosphonium chloride (2, 3 or 4) (10 mmol) in dry THF (63 mL). After stirring for 10min at room temperature, a solution of the appropriate 2H-chromene-3-carbaldehyde (1a or 1b) (10 mmol) or 4-oxo-4H-chromene-3-carbaldehyde (10a or 10b) (10 mmol) in dry THF (43 mL) was added dropwise. The resulting mixture was stirred at room temperature for 20 h. After this period, water was added, THF was removed under reduced pressure and the residue was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulphate, filtered and evaporated to dryness. In the cases of 3-[2-(2H-chromen-3-yl)vinyl]pyridines (6a, 8a) and 4-[2-(2H-chromen-3-yl)vinyl]pyridines (7a, 9a), the obtained mixtures of (E) and (Z) isomers were separated by column chromatography on silica gel, eluting with ethyl acetate/light petroleum (1:1). The (Z) isomer was eluted at first. For the other compounds only one isomer was purified eluting with ethyl acetate/light petroleum (1:1) (6b, 12b), (1:2) (5a, 11a), or (1:3) (5b, 7b, 11b, 12a, 13a, 13b). Compounds 11a, 11b, 13a and 13b were crystallized as hydrochlorides.

Reference： [1]Conti, Cinzia; Proietti Monaco, Luca; Desideri, Nicoletta [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 3, p. 1201 - 1207]

32
[ 42248-31-7 ]
[ 40594-29-4 ]
C₁₆H₉ClF₂N₂O₂ [ No CAS ]

Reference： [1]Indian Journal of Heterocyclic Chemistry,2011,vol. 20,p. 221 - 224

33
[ 13166-10-4 ]
[ 42248-31-7 ]
[ 1609181-45-4 ]

Yield	Reaction Conditions	Operation in experiment
57%	With triethylamine In dichloromethane at 20℃; for 1h; stereoselective reaction;	3 General procedure for the synthesis of compounds (7a-l) General procedure: A solution of 3-formylchromone (1.0mmol), ylidenemalononitrile or ethyl α-cyano-β-methylcinnamate (1.0mmol), and triethylamine (0.014mL, 10%-mol) in dichloromethane (3.0mL) was kept for several hours at room temperature (see Scheme 1). After evaporation of the solvent the product was washed with hot ethanol to give compounds 7 as a colorless powder.

Reference： [1]Korotaev, Vladislav Yu.; Barkov, Alexey Yu.; Kutyashev, Igor B.; Safrygin, Alexander V.; Sosnovskikh, Vyacheslav Ya. [Tetrahedron, 2014, vol. 70, # 22, p. 3584 - 3589]

34
[ 42248-31-7 ]
[ 4865-84-3 ]
C₁₈H₁₀ClNO₃ [ No CAS ]

Reference： [1]Indian Journal of Heterocyclic Chemistry,2012,vol. 22,p. 53 - 60

35
[ 42248-31-7 ]
[ 5818-06-4 ]
(E)-N'-((6-chloro-4-oxo-4H-chromen-3-yl)methylene)-3-hydroxybenzohydrazide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With acetic acid In ethanol at 85℃; for 5h;
77%	With acetic acid In ethanol at 85℃; for 5h;	9.2 Step 2: The purified 6-chloro-3-formylchromone (Compound 35; 60 mg, 0.3 mmol) was reacted with m-Hydroxybenzohydrazide (Compound 36; 45 mg, 0.3 mmol) was reacted with Was dissolved in ethanol (10 mL) contained. Glacial acetic acid was added in a catalytic amount, and the reaction mixture was refluxed at 85 DEG C for 5 hours. Next, the reaction mixture was cooled to room temperature, the solvent was removed in vacuo, The resulting residue was purified by column chromatography to obtain the desired compound (Yield: 77%; m.p: 196-202 [deg.]

Reference： [1]Koh, Dongsoo; Jung, Yearam; Ahn, Seunghyun; Mok, Kenneth Hun; Shin, Soon Young; Lim, Yoongho [Magnetic Resonance in Chemistry, 2017, vol. 55, # 9, p. 864 - 876]
[2]Current Patent Assignee: KONKUK UNIVERSITY - KR2018/130974, 2018, A Location in patent: Paragraph 0148; 0152-0153

36
[ 637-04-7 ]
[ 42248-31-7 ]
(E)-6-chloro-3-((2-m-tolylhydrazono)methyl)-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With acetic acid; In methanol; water; at 60℃; for 0.5h;	General procedure: The warmed solution of phenylhydrazine hydrochloride 2a (0.172 g, 1.2 mmol) and acetic acid (0.5 mL in 1 mL H2O) was added to a stirred solution of 3-formylchromone(0.174 g, 1 mmol) in methanol (2 mL) at room temperature.The reaction mixture was heated to 60 °C for 30 min and then cooled to room temperature. The solid separated was filtered, washed with ice-cold water (5 mL) and then recrystallized from hot methanol providing the corresponding hydrazone 3a. Similarly, the other hydrazones 3b?z were prepared from the corresponding 3-formylchromones 1a?f and phenylhydrazine hydrochlorides 2a?i under optimized reaction conditions

Reference： [1]Acta Chimica Slovenica,2018,vol. 65,p. 34 - 49

37
[ 42248-31-7 ]
[ 57-00-1 ]
[{5-[(5-chloro-2-hydroxyphenyl)carbonyl]pyrimidin-2-yl}(methyl)amino]acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium hydroxide; In ethanol; for 14h;Reflux;	General procedure: A mixture of substituted 3-formylchromones 1(0.01 mol) and compound 2 (0.02 mol) was dissolvedin 20 ml of ethanol and KOH (0.02 mol) was added tothis. The reaction mixture was refluxed for 14 hr. Theprogress of the reaction was monitored by TLC. Aftercompletion of reaction the contents were cooled,poured over crushed ice and acidified with gl aceticacid. The solid obtained was filtered and purified bycrystallization from ethanol to get compound 3.

Reference： [1]Indian Journal of Heterocyclic Chemistry,2015,vol. 24,p. 275 - 280

38
[ 67-56-1 ]
[ 42248-31-7 ]
[ 119256-40-5 ]
C₁₈H₁₁ClF₂N₂O₃S [ No CAS ]

Reference： [1]RSC Advances,2019,vol. 9,p. 20573 - 20581

39
[ 5031-78-7 ]
[ 42248-31-7 ]
6-chloro-3-(3-oxo-3-(4-phenoxy-phenyl)prop-1-enyl)-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With silica supported perchloric acid; In methanol; at 20℃;	General procedure: A mixture of 6/7/8-substituted-3-formyl-4H-chromen-4-one (1a-i, 1.414 moles) and substituted acetophenone/pacetylphenylboronicacid (2a-c/4, 0.9433 moles) was dissolvedin methanol (7.5 ml) and silica-supported perchloricacid (0.035 g, 0.22 mmol) was added to the above solutionand stirred at room temperature till the reactants were completelyconsumed (Scheme 1 & 2, monitored by TLC,EtOAc/CHCl3:C6H14, variable ratio). The methanol wasevaporated under reduced pressure and the resultant cruderesidue was extracted with dichloromethane. The organiclayer was separated and dried over sodium sulfate. The solvent was evaporated to get the crude mixture. Thereafter, theobtained products were purified through recrystallizationusing EtOAc as a solvent and the remaining were subjected toflash column chromatography (silica gel 60-120 mesh, eluentHexane::EtOAc) to yield the purified chromen-4-one-3-ylchalcones (3a-u & 5a-h) as solid powders. The structures ofthese newly obtained chromeno-chalcones (3a-u & 5a-h) werecharacterized spectroscopically (1H-NMR, 13C-NMR, UV, IRand Mass Spectroscopy) [22,23].

Reference： [1]Medicinal Chemistry,2020,vol. 16,p. 212 - 228

40
[ 2252-44-0 ]
[ 42248-31-7 ]
6-chloro-3-(3-(trifluoromethoxy)benzoyl)-4H-chromen-4-one [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 7152 - 7174

41
[ 123-73-9 ]
[ 1576-87-0 ]
[ 42248-31-7 ]
C₁₉H₁₃ClO₃ [ No CAS ]