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

Anary-Abbasinejad, Mohammad; Jaafari, Maryam; Talebizadeh, Mahdiyeh

doi:10.22036/org.chem.2018.135033.1159

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

Document Type : Full Paper

Authors

Mohammad Anary-Abbasinejad ¹

Maryam Jaafari ²

Mahdiyeh Talebizadeh ²

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

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

10.22036/org.chem.2018.135033.1159

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

α-Iminoketones

Isocyanide

Iminopyrans

Four-component reaction

Arylglyoxals