Synthesis and chemiluminescent reactions of some 3-alkoxycarbamoylbenzo[b]furan-2(3H)-ones

The 3-alkoxycarbamoylbenzo[b]furan-2(3H)-ones (1)–(9) have been synthesised, and were found to chemiluminesce in dipolar aprotic solvents in the presence of oxygen and a base. The end products of the chemiluminescent reactions are benzoxazinediones (23), and a mechanism for their formation and the light emission is proposed. A side-reaction gives dehydrodimers (22) which are slowly converted into the benzoxazinediones with weak chemiluminescence