Diastereoselective Synthesis of Structurally and Stereochemically Diversified 2-Oxa-7-azabicyclo[4.1.0]hept-3-enyl Carboxylates and Their Potential Application toward the Synthesis of Functionalized Pyranooxazolone and Pyrrole Derivatives through Skeletal Transformations.

Abstract

An advanced protocol for the diastereoselective intramolecular aziridination reaction has been developed to synthesize 2-oxa-7-azabicyclo[4.1.0]hept-3-en-1-yl carboxylates from their corresponding 4-H-pyrans and spiropyrans analogues employing iodosylbenznene as the exclusive oxidant in the presence of carboxylic acid and triethylamine. High structural and stereochemical diversity of these pyran fused NH-azridine scaffolds makes them useful in evaluating their biological and pharmacological activities by SAR studies. Additionally, their potential synthetic application has been uncovered by efficient transformation into biologically relevant novel pyranooxazolone and pyrrole derivatives.