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AN UNEXPECTED REACTION OF A 3-AMINO-2H-AZIRINE WITH 1,3-BENZOXAZIN-2,4-DIONE


Chandrasekhar, B Parthasarathi; Bieri, Jost H; Heimgartner, Heinz (1982). AN UNEXPECTED REACTION OF A 3-AMINO-2H-AZIRINE WITH 1,3-BENZOXAZIN-2,4-DIONE. Heterocycles, 19:2079-2085.

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.

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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:1982
Deposited On:24 Jul 2014 07:22
Last Modified:18 Apr 2018 11:45
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche & Co. AG, Basel
OA Status:Green
Project Information:
  • : FunderSNSF
  • : Grant ID
  • : Project TitleSwiss National Science Foundation
  • : Funder
  • : Grant ID
  • : Project TitleF. Hoffmann-La Roche & Co. AG, Basel

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