1. 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
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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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