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Communication | Regular issue | Vol 85, No. 2, 2012, pp.305-312
Published online, 22nd December, 2011
DOI: 10.3987/COM-11-12398
Novel Rearrangements of a 8aH-Pyrido[1,2-d]thieno[2’,3’-b][1,4]thiazepine Derivative

Akikazu Kakehi,* Kennosuke Itoh, Hiroyuki Suga, Yuuki Ohkubo, Ayaka Kobayashi, and Takashi Nishi

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


The reaction of 5-ethoxycarbonyl-3-[1-(4-methylpyridinio)]-4-phenythiopene-2-thiolate with dimethyl acetylenedicarboxylate in refluxing chloroform or tetrahydrofuran afforded the corresponding 10H-pyrrolo[1,2-d]thieno[2’,3’-b][1,4]thiazocines or the 6,8-dithia-2-azatetracyclo[,10.03,7]-tetradeca-Δ3,7,4,11,13-tetraene derivative. Also, the thermal conversion from the former product to dimethyl (Z)- and (E)-2-[thieno[2’,3’:2,3][1,4]thiazino[4,5-a]pyrrol-8-ylidene]succinates was confirmed.