[4 + 1 + 1] Annulations of α-Bromo Carbonyls and 1-Azadienes toward Fused Benzoazaheterocycles

Abstract

An unexpected [4 + 1 + 1] annulation between α-bromo carbonyls and 1-azadienes, derived from 2-methylenebenzofuran-3(2 H)-ones or 2-methylenebenzo[ b]thiophene-3(2 H)-ones, has been observed in the presence of DABCO and Cs₂CO₃. These reactions stand in contrast to the common [4 + 1] cyclization reactions of azadienes with the related sulfonium ylides. A range of fused benzofuro[3,2- b]pyridines and benzo[4,5]thieno[3,2- b]pyridines have been efficiently constructed in fair to excellent yields.