Microwave-assisted synthesis of heterocycles from aryldiazoacetates.

Abstract

A novel microwave-assisted method for generation of heterocycles have been explored. A range of 3,4 dihydroquinoxalin-2-ones have been prepared via an N-H insertion/cyclization cascade of dinucleophiles and aryldiazoacetates in moderate to good yields (12 - 80%). Reactions of aryldiazoacetates with o-phenylenediamine generated the best yields, while reactions with aliphatic and benzylic dinucleophiles resulted products in lower yields. Oxidation of 3,4-dihydroquinoxalin-2-one products afforded quinoxaline-2-ol derivatives in good to excellent yields (67 – 95 %).