The NH(C)Br functionality of heteroaromatic compounds as a synthon for fused dihydrooxazoles

Fused dihydrooxazoles are produced by the reaction of 8-bromoteophylline (1), 6-bromo-2-pyridone (7), or 2-bromobenzimidazole (11) with an N-substituted N-(2,3-epoxypropyl)amine. The product derived from 1 undergoes rearrangement to a fused dihydrooxazine while the fused dihydrooxazoles derived from 7 and 11 are stable. J. Heterocyclic Chem., (2011).