Isocyanoalkene Addition–Cyclization–Decarboxylation Cascades

Abstract

A rare conjugate addition to isocyanoalkenes with ethyl cyanoacetate triggers an efficient addition–cyclization–decarboxylation cascade. Using finely dispersed NaOH in THF as a base and nucleophile, is critical in facilitating the proton transfers, the ester hydrolysis, and the subsequent decarboxylation. The strategy provides an efficient route to valuable nitrile-substituted 2,3-dihydro-1H-pyrroles while providing fundamental insight into conjugate additions to isocyanoalkenes.

Key words

isocyanides - isocyanoalkenes - additions - cyclizations - cascades

Publication History

Received: 16 May 2024

Accepted after revision: 13 June 2024

Article published online:
15 July 2024

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