Photoinduced and N-bromosuccinimide-mediated cyclization of 2-azido-N-phenylacetamides

Org Lett. 2013 Aug 2;15(15):3820-3. doi: 10.1021/ol401338e. Epub 2013 Jul 22.

Abstract

An efficient synthesis of quinoxalin-2(1H)-ones or spiro[cyclohexene-1,2'-imidazol]-4'-ones has been achieved in moderate to high yields by the visible light-induced and N-bromosuccinimide-mediated cyclization reaction of 2-azido-N-phenylacetamides at ambient temperature. Both the regioselectivity and the speed of cyclization are affected by the substituents attached to the phenyl ring. For example, quinoxalin-2-ones are produced as the main products when the substrates bear electron-withdrawing groups at the para-position of the phenyl ring; in contrast, spiro[cyclohexene-1,2'-imidazol]-4'-ones are obtained as the main products when the substrates bear electron-donating groups at the para-position.