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Communication | Regular issue | Vol 19, No. 11, 1982, pp.2079-2085
Published online, 1st January, 1970
DOI: 10.3987/R-1982-11-2079
An Unexpected Reaction of a 3-Amino-2H-azirine with 1,3-Benzoxazin-2,4-dione

B. Parthasarathi Chandrasekhar, Jost H. Bieri, Heinz Heimgartner, Gabriel Germain, and Jean-Paul Declercq

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland

Abstract

The reaction of 3-dimethylamino-2,2-dimethyl-2H-azirine (1) with 1,3-benzoxazin-2,4-dione (3) in refluxing 2-propanol led not to the formation of a medium sized heterocycle but to the formation of the imidazo[2,1-b]-1,3-benzoxazin-5-one 4 and the imidazolin-2-one 5 in 33% and 74% yield, respectively. The structure of 4 has been confirmed by X-ray crystallographic analysis while 5 has been identified by comparison with an independently synthesized material (cf. Scheme 2). In Scheme 3 a reaction mechanism for the formation of 4 and 5 is suggested.