I2-Catalyzed cross dehydrogenative coupling: rapid access to benzoxazinones and quinazolinones?

Organic & Biomolecular Chemistry Pub Date: 2017-10-03 DOI: 10.1039/C7OB02038D

Abstract

An efficient and applicable I2-catalyzed intramolecular dehydrogenative C–O/C–N coupling reaction via activating the C–H bond adjacent to the N atom has been developed to provide dozens of substituted benzoxazinones (31 examples) and quinazolinones (5 examples) in good to excellent yields (up to 98%). This one-pot methodology has significant advantages, including a metal-free process, broad substrate scope, high atom economy, and simple operation. This strategy goes through an iminium intermediate followed by nucleophilic attack to provide the desired products.

Graphical abstract: I2-Catalyzed cross dehydrogenative coupling: rapid access to benzoxazinones and quinazolinones
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