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

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.