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Paper | Special issue | Vol 74, No. 1, 2007, pp.521-532
Published online, 2nd October, 2007
DOI: 10.3987/COM-07-S(W)30
First Ring Contraction-Desulfurization of 1-(Arylcarbonyl)pyrido[2,1-c]-1,4-thiazines to 1-(Arylcarbonyl)indolizines and Its Application to 3-Arylthieno[3,2-a]indolizine Synthesis

Akikazu Kakehi,* Hiroyuki Suga, Yuichi Goto, and Nobuhiro Yamaguchi

*Department of Chemistry and Material Engineering, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan


The ring contraction-desulfurization route from transient 1-(arylcarbonyl)pyrido[2,1-c]-1,4-thiazine intermediates, generated in situ from the treatment of the corresponding pyridinium salts with a base and then a dehydrogenation agent, to 1-(arylcarbonyl)indolizines was first observed. By using this route three 1-arylcarbonyl-6,8-dimethylindolizines having the protected 2-thiol group were prepared and their transformation to 2-acyl-3-arylthieno[3,2-a]indolizine derivatives were performed in good yields.