Stereochemistry of 1,3‐dipolar‐cycloaddition of 3,4‐dihydroisoquinoline‐ and 3,4‐dihydro‐carboline‐<i>N</i>‐methoxycarbonyl‐ and <i>N</i>‐phenacyl‐methylides with maleic and fumaric nitrile

Abstract

Abstract magnified image The 1,3‐dipolar‐cycloadditions of two kind of isoquinolinium and carbolinium ylides with fumaric and maleic nitrile resulted in pyrroloisoquinoline and indolizino[8,7‐ b ]indole derivatives, respectively, which are analogues of biologically active alkaloids. The cycloadditions were performed in good yield and proved to be stereoselective. The structure elucidation and complete 1 H and 13 C assignments have been achieved by a combination of various one‐ and two‐dimensional NMR experiments.