Synthesis of Tetrahydroazocino- and Dihydroazepino-1,2-Benzoquinones via Amino-Claisen Rearrangement of 4-(2-Vinyl-Azetidino and Aziridino)-1,2-Benzoquinones

Article abstract of DOI:10.1016/0040-4039(95)00866-B

Amino-Claisen rearrangement of 4-(2-vinyl-azetidino or aziridino)-5-methoxy-1,2-benzoquinones 3a,b selectively gives rise to the new tetrahydroazocino-quinone 4a or dihydroazepino-quinone 4b respectively.Based on paramethoxyphenol as starting material, overall yields for the 3 steps synthesis of heterobicyclic quinones 4a,b are 58 and 52percent.