Light-induced reactions of heteroaryl N-methylanilinomethyl ketones: formation of 3-heteroaryl-1-phenylazetidin-3-ols

Abstract

A series of heteroaryl N-methylanilinomethyl ketones, PhNMe·CH₂COR (R = heteroaryl), were irradiated with ether as the solvent. The corresponding 3-heteroaryl-1-phenylazetidin-3-ols (type II cyclisation products) were formed when R was 2-furyl, benzo[b]furan-2-yl, 2-thienyl, 1-methylpyrrol-2-yl, and 2,4-dimethylthiazol-5-yl, but such products were not isolated when R was pyrrol-2-yl or 3-pyridyl. In some cases, products formed via type II fission were obtained.