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Paper | Special issue | Vol 54, No. 2, 2001, pp.647-665
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)36
New Synthetic Approach to Azuleno[1,2-c]pyrroles and Conversion to Benz[a]azulenes

Dao-Lin Wang and Kimiaki Imafuku*

*Department of Chemistry, Faculty of Science, Kumamoto University, Kurokami, Kumamoto 860-8555, Japan

Abstract

1-Acetyl-2-(bromomethyl)azulenes were obtained as new synthons directed to heterocycle-fused azulenes. 3-Methoxycarbonyl- and 3-cyano-substituted 1-acetyl-2-(bromomethyl)azulenes (3a,b) reacted with anilines (6a-d) in the presence 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-methylazuleno[1,2-c]pyrroles (9ab-ad,ba-bd; 11aa-ad,ba-bd) via cycloadducts.