Simultaneously electrogenerated diene and dienophile: A unique access to novel polyfunctionalized 1,4-benzoxazine derivatives as neuroprotective agents

Abstract

New insights into the scope of a multistep one-pot electrochemical synthesis of polyfunctionalized 2-alkylamino-1,4-benzoxazine derivatives are delineated. This cascade sequence, wherein both cycloaddition partners are generated in situ, at room temperature, under metal-free conditions, should be useful to generate libraries of heterocycles which constitute the molecular framework of medicinally relevant compounds. In this respect, 2-alkylamino-1,4-benzoxazine derivatives proved to be potent neuroprotective agents in vitro, on immortalized HT22 hippocampal cell cultures, and in vivo, in an animal model mimicking the cerebral palsy in human newborns.