Heterocycles

Synthesis of 1, 2-dihydrobenz [c] azepin-3-one via acid-catalyzed cyclization of N-arylmethyl-N-methyl-3-phenylsulfanylacrylamide

Y Horiguchi, T Saitoh, T Kashiwagi, L Katura, M Itagaki…

Index: Horiguchi, Yoshie; Saitoh, Toshiaki; Kashiwagi, Tomoko; Katura, Lisa; Itagaki, Mayumi; Toda, Jun; Sano, Takehiro Heterocycles, 2002 , vol. 57, # 6 p. 1063 - 1077

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Citation Number: 4

Abstract

Résumé/Abstract Treatment of N-arylmethyl-N-methyl-cis-3-phenylsulfanyl acrylamide (5) with p-toluenesulfonic acid induced two reactions; cyclization to 1, 2-dihydrobenz [c] azepin- 3-ones (7) and N-dearylmethylation to N-methylacrylamides (9 and 10) depending on the structures of the substrates. The route provides a simple method of preparing 6-methoxy- (7e), 8-methoxy-(7d), 6, 8-dimethoxy-(7f), and 8, 9-dimethoxy-N-methyl-1, 2-dihydrobenz-[ ...