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Paper | Special issue | Vol 76, No. 1, 2008, pp.391-399
Published online, 25th March, 2008
DOI: 10.3987/COM-08-S(N)20
Preparation of New Nitrogen-Bridged Heterocycles. 63. Unexpected Formation of Thieno[3’,4’:4,5]imidazo[1,2-a]pyridines

Akikazu Kakehi,* Hiroyuki Suga, Atsushi Izumita, and Takashi Abe

*Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, Wakasato, Nagano 380-8553, Japan

Abstract

The alkaline treatment and dehydrogenation of pyridinium salts, obtainable from the S-alkylation of 3,5-dimethylpyridinium 2-alkylthio-1-cyano-2-thioxoethylides with some phenacyl bromides, afforded unexpected heterocycles, 3-alkylthio-1-arylcarbonyl-6,8-dimethylthieno[3’,4’:4,5]imidazo[1,2-a]pyridines, together with the corresponding 2-alkylthio-1-arylcarbonylthio- 6,8-dimethylindolizine-3-carbonitriles.