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Report | Regular issue | Vol 20, No. 12, 1983, pp.2411-2416
Published online, 1st January, 1970
DOI: 10.3987/R-1983-12-2411
Synthesis of Thieno[3,4-c]pyridine and Thieno[3,4-c]azepine Derivatives by N-Acyliminiun Ion-induced Cyclization

Shinzo Kano, Yoko Yuasa, Tsutomu Yokomatsu, and Shoroshi Shibuya

*School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan


Reduction of N-[2-(3-thienyl)]ethylthiazolidine-2,4-diones (3a and 3b) with diisobutylaluminum hydride followed by treatment of the reduction products with formic acid at 60 °C for 14 h yielded the corresponding thieno[3,4-c]pyridines (5a and 5b), respectively. In a similar way, thieno[3,4-c]pyridines (5c - 5e) and thieno[3,4-c]azepines (9a, 9b and 9d) were obtained from the corresponding N-substituted hydroxyoxazolidinone, hydroxyimidazolidinones and hydroxythiazolidinones.