A facile entry into a novel class of dispiroheterocycles through 1,3-dipolar cycloaddition

Abstract

The cycloaddition reaction of non-stabilized azomethine ylides, generated through decarboxylation and deprotonation, with (E)-2-arylidene-1-tetralones as dipolarophile has been investigated. A high degree of regioselectivity has been observed in the synthesis of a new class of functionalised dispiroheterocyclic compounds bearing a tetralone, acenapthenequinone and oxindole framework.

Regio- and Stereoselective Synthesis of a Library of Bioactive Dispiro-Oxindolo/Acenaphthoquino Andrographolides via 1,3-Dipolar Cycloaddition Reaction Under Microwave Irradiation

“…Anti -ylides are involved in the reactions which add to dipolarophiles to form the cycloadducts. Formation of syn -ylide is not observed because of the unfavorable steric repulsion between the carbonyl group of oxindole and methyl group of sarcosine or benzyl group of N -benzyl glycine …”

Heterogeneous graphene oxide as recyclable catalyst for azomethine ylide mediated 1,3 dipolar cycloaddition reaction in aqueous medium

“…12 a There are very few reports in the literature on aqueous 1,3 dipolar cycloaddition reactions involving azomethine ylides is reported. 18 We believe a robust, rapid, highly selective, green method for the synthesis of spiro molecules is of high value.…”