Synthesis of 2‐Alkyl‐Substituted Benzimidazoles by Thermal Decomposition of 2‐Azidobenzenamines in thePresence of an Aldehyde

Abstract

2‐Substituted benzimidazoles were prepared by reaction of 2‐azidoaminobenzenes with aldehydes under thermal conditions. The reaction probably proceeds via a sequential imine formation, azide decomposition forming a nitrene, and electrocyclization.

Keywords:

• Alkaloids
• azide
• benzimidazole
• nitrene

Acknowledgment

Support has been provided by a grant from the National Institutes of Health (R01 GM57416). National Science Foundation's Experimental Program to Stimulate Competitive Research (NSF‐EPSCoR) (grant no. 1002165R) is gratefully acknowledged for the funding of a 600‐MHz Varian Inova NMR and the NMR facility in the C. Eugene Bennett Department of Chemistry at West Virginia University.