New synthetic approach to azuleno[1,2-c]pyrroles and conversion to benz[a]azulenes

1-Acetyl-2-(bromomethyl)azulenes were obtained as new synthons directed to heterocycle-fused azulenes. 3-Methoxycarbonyl- and 3-cyano-substituted 1-ac etyl-2-(bromomethyl)azulenes (3a,b) reacted with anilines (6a-d) in the pre sence of potassium carbonate to afford 9-substituted 2-aryl-3-methylazuleno [1,2-c]pyrrole (7aa-ad,ba-bd) in moderate to good yields. These azuleno-[1, 2-c]pyrroles (7aa-ad,ba-bd) were condensed with acetylenedicarboxylates to give 1-anilino-2,3-dialkoxycarbonyl-4-methylbenz[a]azulenes (8aa-ad,ba, bb, bd; 10aa-ad,ba-bd) and 2-aryl-1-(1,2-dialkoxycarbonylethenyl)-4-methyl-azul eno[1,2-c]pyrroles (9ab-ad,ba-bd; 11aa-ad,ba-bd) via cycloadducts.