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Communication | Regular issue | Vol 19, No. 6, 1982, pp.1033-1037
Published online, 1st January, 1970
DOI: 10.3987/R-1982-06-1033
A Synthesis of Benzo[b]naphthoi[2,3-d]thiophene Derivatives via Benzo[b]thiophene-2,3-quinodimethane Intermediates

Shinzo Kano, Naoki Mochizuki, Yoko Yuasa, Satoshi Hibino, and Shiroshi Shibuya

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


2-Methyl- and 2-ethyl-3-(α-aryl)hydroxymetylbenzo[b]thiophene (6a)-(6d) were heated at 400 °C for 5 min to yield the corresponding benzo[b]naphtho[2,3-d]thiophene derivatives (9a)-(9d), respectively, In a similar fashion, the alcohol (8a) gave 5-methylbenzo[b]naphtho[2,3-d]thiophene (9e) and 5,10-dimethyl derivative (3). 8-Methoxy-5-methyl- (9f) and 5-phenyl derivative (9g) were obtained from the corresponding alcohols (8b) and (8c), respectively.