Synthesis of benzopyranopyrrolidines via 1,3-dipolar cycloaddition of nonstabilized azomethine ylides with 3-substituted coumarins

Abstract

A three-component reaction of 3-substituted coumarins with N-alkyl-α-amino acids and aldehydes gave 1-benzopyrano[3,4-c]pyrrolidines as a result of a 1,3-dipolar cycloaddition of an intermediate nonstabilized azomethine ylide at the double bond of the coumarin system in moderate to good yields. In most cases, high regio- and stereo-selectivity of the [3+2] cycloaddition was observed. © 2013 Elsevier Ltd. All rights reserved.