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Paper | Regular issue | Vol 65, No. 10, 2005, pp.2451-2459
Published online, 12th August, 2005
DOI: 10.3987/COM-05-10514
Syntheses and Reactions of 2-Cyclohexyl-1,3,4,5-tetrahydro-10H-pyrrolo[3,4-b][1,5]benzodiazepine-1,4-dione and 4-Aryl-2-cyclohexyl-1,3,4,10-tetrahydropyrrolo[4,3-c][1,5]benzothiazepin-1-ones

Keizo Matsuo,* Junko Kawanishi, Mariko Kobayashi, and Sachiko Ueno

*Faculty of Pharmaceutical Sciences, Kinki University, 3-4-1, Kowakae, Higashi-Osaka 577-8502, Japan

Abstract

2-Cyclohexyl-1,3,4,5-tetrahydro-10H-pyrrolo[3,4-b][1,5]benzodiazepine-1,4-dione was synthesized by heating a solution of ethyl 1-cyclohexyl-2,3-dioxopyrrolidine-4-carboxylate and o-phenylenediamine in acetic acid. Alkylation and acylation of the synthesized compound were examined. 4-Aryl-2-cyclohexyl-1,3,4,10-tetrahydropyrrolo[4,3-c][1,5]benzothiazepin-1-ones were synthesized by Michael addition of 2-aminothiophenol to 4-arylidene-1-cyclohexyl-2,3-dioxopyrrolidines and concomitant dehydrative cyclization.