One-pot Four-component Reaction between Arylamines, Arylglyoxals, Cyclohexyl Isocyanide, and Acetylene Diesters: An Efficient Synthesis of 2H-iminopyran Derivatives

Document Type: Research Paper

Authors

1 Department of chemistry, Vali-e-Asr University, Rafsanjan, 77176, Iran

2 Department of Chemistry, Vali-e-Asr University,Rafsanjan 77176, Iran

Abstract

A facile synthesis of highly functionalized 2H-iminopyran derivatives by the multi-component reaction of cyclohexyl isocyanide, dialkyl acetylenedicarboxylates, arylglyoxals and arylamines is described. The zwitterionic intermediate produced by addition of cyclohexyl isocyanide to electron-deficient acetylene diesters was trapped by the electrophilic imine moiety of α-iminoketones, derived from arylglyoxals and arylamines, to afford an inner salt intermediate which converted to 2H-iminopyran derivatives by an intramolecular cyclization.

Keywords