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Paper | Regular issue | Vol 34, No. 1, 1992, pp.103-110
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5897
A Simple Route to 2,3-Dihydronaphtho[1,2-b]thiophenes and Naphtho[1,2-b]thiophenes Bearing Trifluoromethyl Groups by Aromatic Nucleophilic Substitution of N,N-Dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine

Etsuji Okada, Ryoichi Masuda, Masaru Hojo,* Naonori Imazaki, and Hiroshi Miya

*Department of Industrial Chemistry, Faculty of Engineering, Kobe University, Kobe 657, Japan

Abstract

2,3-Dihydronaphtho[1,2-b]thiophenes (2, 4, 5, and 7) and naphtho[1,2-b]thiophenes (3 and 8) bearing trifluoromethyl groups were easily synthesized by aromatic nucleophilic nitrogen-sulfur exchange reaction of N,N-dimethyl-2,4-bis(trifluoroacetyl)-1-naphthylamine (1) with thioglycolic acids and with benzyl mercaptan, followed by cyclization (cyclodehydration).