Triple-Consecutive Isocyanide Insertions with Aldehydes: Synthesis of 4-Cyanooxazoles

Abstract

An efficient TMSOTf-promoted selective triple consecutive insertions of tert -butyl isocyanide into aldehydes has been developed, affording pharmacological interesting 4-cyanooxazoles in high yields in a one pot manner. The given method encompasses a wide range of substrates with tert -butyl isocyanide serving as sources of critical “CN” and “C–N═C” moieties. The versatile transformations of the resulting 4-cyanooxazoles were demonstrated. The key reaction intermediates for plausible mechanisms were determined.