Open Access Open Access  Restricted Access Subscription Access

3-NITRO-2H-CHROMENES IN [3+2] CYCLOADDITION REACTION WITH AZOMETHINE YLIDES DERIVED FROM N-UNSUBSTITUTED α-AMINO ACIDS AND ISATINS: REGIO- AND STEREOSELECTIVE SYNTHESIS OF SPIROCHROMENO[3,4-c]PYRROLIDINES

Игорь Б. Кутяшев, Алексей Ю. Барков, Владислав Ю. Коротаев, Вячеслав Я. Сосновских
Cover Image

Abstract


A regio- and stereoselective method was developed for the synthesis of tetrahydro-4H-spiro[chromeno[3,4-c]pyrrole-1,3'-indolin]-2'-ones in 72−96% yields, using a three-component reaction of 3-nitro-2-trifluoromethyl- and 3-nitro-2-phenyl-2H-chromenes with azomethine ylides that were generated in situ from N-unsubstituted α-amino acids and isatins.

Keywords


isatins; N-unsubstituted α-amino acids; 3-nitro-2H-chromenes; spirochromeno[3,4-c]pyrrolidines; stabilized azomethine ylides; 1,3-dipolar cycloaddition

Full Text: PDF (Russian) Supplementary File(s): None


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv