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Note | Regular issue | Vol 81, No. 1, 2010, pp.175-184
Published online, 6th November, 2009
DOI: 10.3987/COM-09-11852
Preparation of New Nitrogen-Bridged Heterocycles. 68. One-Pot Synthesis of 4-Substituted 5-Acylthieno[3,2-d]thiazole Derivatives

Akikazu Kakehi,* Hiroyuki Suga, Yukihisa Okumura, and Takashi Nishi

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


The reactions of 5-acyl-3-(1-pyridinio)thiophene-2-thiolates with dimethyl acetylenedicarboxylate in xylene at the reflux temperature afforded the corresponding 2-unsubstituted 5-acylthieno[3,2-d]thiazoles in 2569% yields together with dimethyl phthalate as another fragmentation product. In a few reactions, the unexpected products, dimethyl 2-[2-acylthieno[2’,3’:2,3]-1,4-thiazino[4,5-a]pyrrol-8-ylidene]succinate derivatives, were also isolated, though their yields were very low.