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Vyacheslav Ya. Sosnovskikh - One of the best experts on this subject based on the ideXlab platform.
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uncatalyzed highly stereoselective addition of α morpholinostyrene to 3 nitro 2 trihalomethyl 2h chromenes synthesis of trans cis and trans trans 3 nitro 4 phenacyl 2 trihalomethyl chromanes
ChemInform, 2016Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Mikhail I Kodess, Igor B Kutyashev, Ivan V Kotovich, Vyacheslav Ya. SosnovskikhAbstract:Abstract Reactions of 2-R-3-nitro-2H-chromenes (R=CF3, CCl3, Ph) with α-morpholinostyrene in acetonitrile proceed diastereoselectively to give mainly trans–cis-2,3,4-trisubstituted chromane enamines at room temperature and trans–trans-chromane enamines at 60 °C as a result of nucleophilic addition at the C-4 atom of the chromene system. Acid hydrolysis of these compounds proceeded with retention of the configuration of the pyran ring and gave 4-phenacylchromanes. The stereochemistry of the products was established by X-ray diffraction analysis.
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highly regio and stereoselective addition of aminoenones to 2 substituted 3 nitro 2h chromenes unexpected synthesis of 5 trifluoromethyl 5h chromeno 3 4 b pyridines
Tetrahedron, 2015Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Marina A Ezhikova, Mikhail I Kodess, Igor B Kutyashev, Ivan V Kotovich, Vyacheslav Ya. SosnovskikhAbstract:Reactions of 2-R-3-nitro-2H-chromenes (R=CF3, CCl3, Ph) with aminoenones derived from acetylacetone and cyclic amines (morpholine, piperidine) proceed diastereoselectively to give mainly cis–trans-2,3,4-trisubstituted chromanes as a result of nucleophilic addition of the vinylogous β-methyl group at the C-4 atom of the chromene system. From these compounds, under acidic conditions, 4-acetoacetonyl-3-nitrochromanes and 5H-chromeno[3,4-b]pyridines, depending on the substituent at the 2-position, were obtained in moderate to good yields. Similar results, except for the synthesis of 5H-chromeno[3,4-b]pyridines, were obtained by replacing acetylacetone with benzoylacetone. The stereochemistry of the products was established by X-ray diffraction analysis.
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synthesis of chromeno 3 4 c 1 2 oxazine n oxides via formal 4 2 cycloaddition of 3 nitro 2 trihalomethyl 2h chromenes with cyclohexanone and pinacolone enamines
Tetrahedron, 2014Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Mikhail I Kodess, Evgeniya G Matochkina, Vyacheslav Ya. SosnovskikhAbstract:Abstract 3-Nitro-2-trichloro(trifluoro)methyl-2H-chromenes undergo a formal [4+2] cycloaddition reaction to cyclohexanone and pinacolone enamines, producing chromeno[3,4-c][1,2]benzoxazin-6-oxides with high diastereoselectivity and in good yields. In addition, some novel 2,3,4-trisubstituted chromanes were obtained. The stereochemistry of the products was established based on a 2D NOESY experiment and an X-ray diffraction study.
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highly diastereoselective 1 3 dipolar cycloaddition of nonstabilized azomethine ylides to 3 nitro 2 trihalomethyl 2h chromenes synthesis of 1 benzopyrano 3 4 c pyrrolidines
ChemInform, 2014Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Mikhail I Kodess, Evgeniya G Matochkina, Vladimir S Moshkin, Vyacheslav Ya. SosnovskikhAbstract:Reactions of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes, including 2-unsubstituted derivatives, with N-alkyl-a-amino acids (sarcosine, proline) and paraformaldehyde proceed diastereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate nonstabilized azomethine ylide at the D 3 -bond of the chromene system.
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domino reaction of 3 nitro 2 trifluoromethyl 2h chromenes with 2 1 phenylalkylidene malononitriles synthesis of functionalized 6 trifluoromethyl 6h dibenzo b d pyrans and a rare case of 1 5 sigmatropic shift of the nitro group
Tetrahedron, 2013Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Vyacheslav Ya. SosnovskikhAbstract:Abstract A variety of functionalized 6-(trifluoromethyl)-6H-dibenzo[b,d]pyrans were easily synthesized in good yields under mild conditions by a domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylethylidene)- and 2-(1-phenylpropylidene)malononitriles. In the latter case, intermediate 7-amino-10-methyl-10-nitro-9-phenyl-6-(trifluoromethyl)-10,10a-dihydro-6H-benzo[c]chromene-8-carbonitriles were isolated as a result of a rare [1,5] sigmatropic shift of the nitro group.
M P S Ishar - One of the best experts on this subject based on the ideXlab platform.
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cytotoxic activity of 3 5 phenyl 3h 1 2 4 dithiazol 3 yl chromen 4 ones and 4 oxo 4h chromene 3 carbothioic acid n phenylamides
European Journal of Medicinal Chemistry, 2010Co-Authors: Tilak Raj, Richa Kaur Bhatia, Ashish Kapur, Madhunika Sharma, Ajit Kumar Saxena, M P S IsharAbstract:Abstract 6/6,7-Substituted-3-formylchromones (8a–g) were reacted with 2 equivalents thiobenzamide (9) in refluxing toluene to furnish substituted-3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones (10a–g) in high yields. Similarly, when substituted-2-anilino-3-formylchromones (8a–d) were reacted with thiobenzamide (9, 2 equivalents) in refluxing xylene, 4-oxo-4H-Chromene-3-carbothioic acid N-phenylamides (11a–d) were obtained in high yields. All the compounds (10a–g) and (11a–d) display significant cytotoxic activity against a number of human cancer cell lines. Among these compounds 10e (IC50 = 10 μM), 10b (IC50 = 14.6 μM) and 10a (IC50 = 10.5 μM) showed maximum cytotoxic activity on neuroblastoma. Also, the compound 10c (IC50 = 10.5 μM) showed maximum cytotoxic activity on ovarian cancer cell line.
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mechanism of unusual formation of 3 5 phenyl 3h 1 2 4 dithiazol 3 yl chromen 4 ones and 4 oxo 4h chromene 3 carbothioic acid n phenylamides and their antimicrobial evaluation
European Journal of Medicinal Chemistry, 2009Co-Authors: Tilak Raj, Vivek K Gupta, Richa Kaur Bhatia, Rakesh Kumar Sharma, Deepak Sharma, M P S IsharAbstract:Abstract 6/6,7-Substituted 3-formylchromones (9a–e) react with 2 equivalents of 2-phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene (10) or thiobenzamide (11) in refluxing toluene to furnish novel substituted 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones (12a–e). However, reactions of substituted 2-anilino-3-formylchromones (15a–d) with thiobenzamide (11, 2 equivalents) in refluxing xylene furnish 4-oxo-4H-Chromene-3-carbothioic acid N-phenylamide (17a–d) in high yields. A mechanistic rationalization of the conversion of 2-anilino-3-formylchromones (15a–d) to N-phenylamides (17a–d), and 3-formylchromones (9a–e) to the corresponding thioaldehydes, is proffered. All the compounds (12a–e, 17a–d) display very high antifungal and antibacterial activities against a number of strains. Dithiazole 12d exhibits a very high antifungal activity (MIC 5 μg/ml) against Geotrichum candidum, better than fluconazole (MIC 09 μg/ml) and also possesses good antibacterial activity (MIC 52 μg/ml) against Shigella flexneri.
Vladislav Yu. Korotaev - One of the best experts on this subject based on the ideXlab platform.
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uncatalyzed highly stereoselective addition of α morpholinostyrene to 3 nitro 2 trihalomethyl 2h chromenes synthesis of trans cis and trans trans 3 nitro 4 phenacyl 2 trihalomethyl chromanes
ChemInform, 2016Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Mikhail I Kodess, Igor B Kutyashev, Ivan V Kotovich, Vyacheslav Ya. SosnovskikhAbstract:Abstract Reactions of 2-R-3-nitro-2H-chromenes (R=CF3, CCl3, Ph) with α-morpholinostyrene in acetonitrile proceed diastereoselectively to give mainly trans–cis-2,3,4-trisubstituted chromane enamines at room temperature and trans–trans-chromane enamines at 60 °C as a result of nucleophilic addition at the C-4 atom of the chromene system. Acid hydrolysis of these compounds proceeded with retention of the configuration of the pyran ring and gave 4-phenacylchromanes. The stereochemistry of the products was established by X-ray diffraction analysis.
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highly regio and stereoselective addition of aminoenones to 2 substituted 3 nitro 2h chromenes unexpected synthesis of 5 trifluoromethyl 5h chromeno 3 4 b pyridines
Tetrahedron, 2015Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Marina A Ezhikova, Mikhail I Kodess, Igor B Kutyashev, Ivan V Kotovich, Vyacheslav Ya. SosnovskikhAbstract:Reactions of 2-R-3-nitro-2H-chromenes (R=CF3, CCl3, Ph) with aminoenones derived from acetylacetone and cyclic amines (morpholine, piperidine) proceed diastereoselectively to give mainly cis–trans-2,3,4-trisubstituted chromanes as a result of nucleophilic addition of the vinylogous β-methyl group at the C-4 atom of the chromene system. From these compounds, under acidic conditions, 4-acetoacetonyl-3-nitrochromanes and 5H-chromeno[3,4-b]pyridines, depending on the substituent at the 2-position, were obtained in moderate to good yields. Similar results, except for the synthesis of 5H-chromeno[3,4-b]pyridines, were obtained by replacing acetylacetone with benzoylacetone. The stereochemistry of the products was established by X-ray diffraction analysis.
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synthesis of chromeno 3 4 c 1 2 oxazine n oxides via formal 4 2 cycloaddition of 3 nitro 2 trihalomethyl 2h chromenes with cyclohexanone and pinacolone enamines
Tetrahedron, 2014Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Mikhail I Kodess, Evgeniya G Matochkina, Vyacheslav Ya. SosnovskikhAbstract:Abstract 3-Nitro-2-trichloro(trifluoro)methyl-2H-chromenes undergo a formal [4+2] cycloaddition reaction to cyclohexanone and pinacolone enamines, producing chromeno[3,4-c][1,2]benzoxazin-6-oxides with high diastereoselectivity and in good yields. In addition, some novel 2,3,4-trisubstituted chromanes were obtained. The stereochemistry of the products was established based on a 2D NOESY experiment and an X-ray diffraction study.
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highly diastereoselective 1 3 dipolar cycloaddition of nonstabilized azomethine ylides to 3 nitro 2 trihalomethyl 2h chromenes synthesis of 1 benzopyrano 3 4 c pyrrolidines
ChemInform, 2014Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Mikhail I Kodess, Evgeniya G Matochkina, Vladimir S Moshkin, Vyacheslav Ya. SosnovskikhAbstract:Reactions of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes, including 2-unsubstituted derivatives, with N-alkyl-a-amino acids (sarcosine, proline) and paraformaldehyde proceed diastereoselectively to give 1-benzopyrano[3,4-c]pyrrolidines in good yields as a result of a 1,3-dipolar cycloaddition of the intermediate nonstabilized azomethine ylide at the D 3 -bond of the chromene system.
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domino reaction of 3 nitro 2 trifluoromethyl 2h chromenes with 2 1 phenylalkylidene malononitriles synthesis of functionalized 6 trifluoromethyl 6h dibenzo b d pyrans and a rare case of 1 5 sigmatropic shift of the nitro group
Tetrahedron, 2013Co-Authors: Vladislav Yu. Korotaev, Alexey Yu. Barkov, Vyacheslav Ya. SosnovskikhAbstract:Abstract A variety of functionalized 6-(trifluoromethyl)-6H-dibenzo[b,d]pyrans were easily synthesized in good yields under mild conditions by a domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylethylidene)- and 2-(1-phenylpropylidene)malononitriles. In the latter case, intermediate 7-amino-10-methyl-10-nitro-9-phenyl-6-(trifluoromethyl)-10,10a-dihydro-6H-benzo[c]chromene-8-carbonitriles were isolated as a result of a rare [1,5] sigmatropic shift of the nitro group.
Tilak Raj - One of the best experts on this subject based on the ideXlab platform.
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cytotoxic activity of 3 5 phenyl 3h 1 2 4 dithiazol 3 yl chromen 4 ones and 4 oxo 4h chromene 3 carbothioic acid n phenylamides
European Journal of Medicinal Chemistry, 2010Co-Authors: Tilak Raj, Richa Kaur Bhatia, Ashish Kapur, Madhunika Sharma, Ajit Kumar Saxena, M P S IsharAbstract:Abstract 6/6,7-Substituted-3-formylchromones (8a–g) were reacted with 2 equivalents thiobenzamide (9) in refluxing toluene to furnish substituted-3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones (10a–g) in high yields. Similarly, when substituted-2-anilino-3-formylchromones (8a–d) were reacted with thiobenzamide (9, 2 equivalents) in refluxing xylene, 4-oxo-4H-Chromene-3-carbothioic acid N-phenylamides (11a–d) were obtained in high yields. All the compounds (10a–g) and (11a–d) display significant cytotoxic activity against a number of human cancer cell lines. Among these compounds 10e (IC50 = 10 μM), 10b (IC50 = 14.6 μM) and 10a (IC50 = 10.5 μM) showed maximum cytotoxic activity on neuroblastoma. Also, the compound 10c (IC50 = 10.5 μM) showed maximum cytotoxic activity on ovarian cancer cell line.
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mechanism of unusual formation of 3 5 phenyl 3h 1 2 4 dithiazol 3 yl chromen 4 ones and 4 oxo 4h chromene 3 carbothioic acid n phenylamides and their antimicrobial evaluation
European Journal of Medicinal Chemistry, 2009Co-Authors: Tilak Raj, Vivek K Gupta, Richa Kaur Bhatia, Rakesh Kumar Sharma, Deepak Sharma, M P S IsharAbstract:Abstract 6/6,7-Substituted 3-formylchromones (9a–e) react with 2 equivalents of 2-phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene (10) or thiobenzamide (11) in refluxing toluene to furnish novel substituted 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones (12a–e). However, reactions of substituted 2-anilino-3-formylchromones (15a–d) with thiobenzamide (11, 2 equivalents) in refluxing xylene furnish 4-oxo-4H-Chromene-3-carbothioic acid N-phenylamide (17a–d) in high yields. A mechanistic rationalization of the conversion of 2-anilino-3-formylchromones (15a–d) to N-phenylamides (17a–d), and 3-formylchromones (9a–e) to the corresponding thioaldehydes, is proffered. All the compounds (12a–e, 17a–d) display very high antifungal and antibacterial activities against a number of strains. Dithiazole 12d exhibits a very high antifungal activity (MIC 5 μg/ml) against Geotrichum candidum, better than fluconazole (MIC 09 μg/ml) and also possesses good antibacterial activity (MIC 52 μg/ml) against Shigella flexneri.
Vivek K Gupta - One of the best experts on this subject based on the ideXlab platform.
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salicyldimine based schiff s complex of copper ii as an efficient catalyst for the synthesis of nitrogen and oxygen heterocycles
New Journal of Chemistry, 2015Co-Authors: Manjulla Gupta, Monika Gupta, Vivek K GuptaAbstract:In the present paper, we have reported the synthesis of an imine-based silica-functionalized copper(II) catalyst using salicyldehyde as a ligand. Furthermore, the catalyst is characterized through various spectroscopic techniques, namely FTIR, XRD, TGA, EDX, XPS, SEM, TEM and AAS. Herein, we have studied its applications in the synthesis of the oxygen-containing heterocyclic 2-amino-4H-Chromenes and the nitrogen-containing heterocyclic acridinones. A single crystal X-ray analysis of 2-amino-4-(4-chlorophenyl)-6,6,8,8-tetrahydro-7,7-dimethyl-5-oxo-4H-Chromene-3-carbonitrile has revealed that the compound crystallizes in a monoclinic crystal system with space group P21/n.
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mechanism of unusual formation of 3 5 phenyl 3h 1 2 4 dithiazol 3 yl chromen 4 ones and 4 oxo 4h chromene 3 carbothioic acid n phenylamides and their antimicrobial evaluation
European Journal of Medicinal Chemistry, 2009Co-Authors: Tilak Raj, Vivek K Gupta, Richa Kaur Bhatia, Rakesh Kumar Sharma, Deepak Sharma, M P S IsharAbstract:Abstract 6/6,7-Substituted 3-formylchromones (9a–e) react with 2 equivalents of 2-phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene (10) or thiobenzamide (11) in refluxing toluene to furnish novel substituted 3-(5-phenyl-3H-[1,2,4]dithiazol-3-yl)chromen-4-ones (12a–e). However, reactions of substituted 2-anilino-3-formylchromones (15a–d) with thiobenzamide (11, 2 equivalents) in refluxing xylene furnish 4-oxo-4H-Chromene-3-carbothioic acid N-phenylamide (17a–d) in high yields. A mechanistic rationalization of the conversion of 2-anilino-3-formylchromones (15a–d) to N-phenylamides (17a–d), and 3-formylchromones (9a–e) to the corresponding thioaldehydes, is proffered. All the compounds (12a–e, 17a–d) display very high antifungal and antibacterial activities against a number of strains. Dithiazole 12d exhibits a very high antifungal activity (MIC 5 μg/ml) against Geotrichum candidum, better than fluconazole (MIC 09 μg/ml) and also possesses good antibacterial activity (MIC 52 μg/ml) against Shigella flexneri.
