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Your search keyword '"3-NITRO-2H-CHROMENES"' showing total 3 results
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3 results on '"3-NITRO-2H-CHROMENES"'

1. Green and Efficient Construction of Chromeno[3,4-c]pyrrole Core via Barton–Zard Reaction from 3-Nitro-2H-chromenes and Ethyl Isocyanoacetate

Author

Alexey Barkov, Ivan Kochnev, Vyacheslav Sosnovskikh, Vladislav Korotaev, and Nikolay Zimnitskiy

Subjects
3-nitro-2H-chromenes, ethyl isocyanoacetate, Barton–Zard reaction, 2,4-dihydrochromeno[3,4-c]pyrroles, Chemistry (miscellaneous), Organic Chemistry, Drug Discovery, Molecular Medicine, Pharmaceutical Science, Physical and Theoretical Chemistry, Analytical Chemistry
Abstract

A regioselective one-pot method for the synthesis of 1-ethyl 2,4-dihydrochromene[3,4-c]pyrroles in 63–94% yields from available 2-phenyl-, 2-trifluoro(trichloro)methyl- or 2-phenyl-2-(trifluoromethyl)-3-nitro-2H-chromenes and ethyl isocyanoacetate through the Barton–Zard reaction in ethanol at reflux for 0.5 h, using K2CO3 as a base, has been developed.

Published
2022
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2. 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

Author

Vladislav Yu. Korotaev, Mikhail I. Kodess, Evgeniya G. Matochkina, Vyacheslav Ya. Sosnovskikh, Alexey Yu. Barkov, and Vladimir S. Moshkin

Subjects
3-NITRO-2H-CHROMENES, 2 METHYL 8 METHOXY 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE, Azomethine ylide, 2 METHYL 8 METHOXY 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE, UNCLASSIFIED DRUG, 2 METHYL 8 METHOXY 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE, Biochemistry, Medicinal chemistry, 8 BROMO 2 METHYL 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE, chemistry.chemical_compound, Drug Discovery, 2 METHYL 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE, 6A NITRO 6 (TRIFLUOROMETHYL) 6,6A,6B,7,8,9,11,11A OCTAHYDROCHROMENO[3,4 A]PYRROLIZINE, PRIORITY JOURNAL, Paraformaldehyde, STEREOCHEMISTRY, CHROMENE DERIVATIVE, 2 METHYL 3A,8 DINITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE, 2 METHYL 3A,8 DINITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE, Chemistry, 2 BROMO 6A NITRO 6 (TRICHLOROMETHYL) 6,6A,6B,7,8,9,11,11A OCTAHYDROCHROMENO[3,4 A]PYRROLIZINE, 2 BROMO 6A NITRO 6 (TRIFLUOROMETHYL) 6,6A,6B,7,8,9,11,11A OCTAHYDROCHROMENO[3,4 A]PYRROLIZINE, Cycloaddition, Drug synthesis, 2 METHYL 3A,8 DINITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE, 1,3-Dipolar cycloaddition, 6A NITRO 6 PHENYL 6,6A,6B,7,8,9,11,11A OCTAHYDROCHROMENO[3,4 A]PYRROLIZINE, AZOMETHINE YLIDE, 8 BROMO 2 METHYL 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE, CYCLOADDITION, Sarcosine, 1-BENZOPYRANO[3,4-C]PYRROLIDINES, TRIFLUORO, 2 METHYL 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE, METHYL 2 METHYL 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE 3A CARBOXYLATE, PYRROLIDINE DERIVATIVE, PARAFORMALDEHYDE, ARTICLE, 2 METHYL 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE 3A CARBONITRILE, 2 METHYL 8 METHOXY 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE, DRUG SYNTHESIS, Organic Chemistry, 1,3-DIPOLAR CYCLOADDITION, CONTROLLED STUDY, NONSTABILIZED AZOMETHINE YLIDES, 8 BROMO 2 METHYL 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE, Nitro, 2 METHYL 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE, 8 BROMO 2 METHYL 3A NITRO 4 (TRICHLOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE, 2 METHYL 3A NITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE OXALATE, 2 METHYL 3A,8 DINITRO 4 (TRIFLUOROMETHYL) 1,2,3,3A,4,9B HEXAHYDROCHROMENO[3,4 C]PYRROLE
Abstract

Reactions of 3-nitro-2-trifluoro(trichloro)methyl-2H-chromenes, including 2-unsubstituted derivatives, with N-alkyl-α-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 Δ3-bond of the chromene system. © 2013 Elsevier Ltd. All rights reserved.

Published
2013
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3. Synthesis of 5-(trifluoromethyl)-5H-chromeno[3,4-b]pyridines from 3-nitro-2-(trifluoromethyl)-2H-chromenes and aminoenones derived from acetylacetone and cyclic amines

Author

Vyacheslav Ya. Sosnovskikh, Vladislav Yu. Korotaev, and Alexey Yu. Barkov

Subjects
3-NITRO-2H-CHROMENES, NUCLEOPHILICITY, Acetylacetone, 5 (TRIFLUOROMETHYL) 5H CHROMENO[3,4 BETA]PYRIDINE DERIVATIVE, CHROMANES, Substituent, SYNTHESIS, UNCLASSIFIED DRUG, AMINE, Biochemistry, chemistry.chemical_compound, Nucleophile, Drug Discovery, Organic chemistry, ARTICLE, CHROMAN DERIVATIVE, STEREOCHEMISTRY, CHROMENE DERIVATIVE, Trifluoromethyl, Nucleophilic addition, QUANTUM YIELD, Chemistry, CHEMICAL STRUCTURE, Organic Chemistry, ACETYLACETONE, ATOM, METHYL GROUP, 4 ACETOACETONYL 3 NITRO 2 (TRIFLUOROMETHYL) 2H CHROMENE DERIVATIVE, MICHAEL ADDITION, Nitro, Michael reaction, CHROMENO[3,4-B]PYRIDINES, PYRIDINE DERIVATIVE, PUSH-PULL ENAMINES, Methyl group
Abstract

Reactions of 3-nitro-2H-chromenes with aminoenones derived from acetylacetone and cyclic amines proceed diastereoselectively to give functionalized 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, 5-(trifluoromethyl)-5H- chromeno[3,4-b]pyridines and 4-acetoacetonyl-3-nitro-2-(trichloromethyl/phenyl) chromanes, depending on the substituent at the 2-position, were obtained in moderate to good yields. © 2013 Elsevier Ltd. All rights reserved.

Published
2013
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