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Paper | Regular issue | Vol 55, No. 10, 2001, pp.1919-1926
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9325
Heterocyclization of 4-Trifluoroacetyl-1,3-oxazolium-5-olates with 1,4-Bis-nucleophiles

Masami Kawase,* Hiromi Koiwai, Toru Tanaka, Satoru Tani, and Hiroshi Miyamae

*Josai University, Faculty of Pharmaceutical Sciences, Faculty of Pharmaceutical Sciences1-1 Keyakidai, Sakado, Saitama 350-0295, Japana

Abstract

Reactions of aromatic 1,4-bis -nucleophiles such as o-phenylenediamine and o-aminothiophenol, with mesoionic 4-trifluoroacetyl-1,3-oxazolium-5-olates (1) gave regiospecifically seven member trifluoromethylated heterocycles such as 1,5-benzodiazepines (3) and 1,5-benzothiazepines (4). The reaction with o-aminophenol afforded non-cyclized products (5). The structures of 3, 4, and 5 were established by X-Ray diffraction analysis.