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Organic & biomolecular chemistry

Chemical generation of o-quinone monoimines for the rapid construction of 1,4-benzoxazine derivatives.


PMID 22286300

Abstract

Highly reactive o-benzoquinone monoimines were chemically generated and successfully trapped with electron-rich olefins that led to the synthesis of hitherto unknown 1,4-benzoxazine derivatives. This unprecedented transformation was achieved by the oxidation of o-aminophenols bearing appropriate functionality on the arene residue with less expensive hypervalent iodine reagent in the presence of vinylic ethers or thioethers.