UZH-Logo

Maintenance Infos

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.

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.

Downloads

50 downloads since deposited on 24 Jul 2014
36 downloads since 12 months
Detailed statistics

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:05 Apr 2016 17:58
Publisher:The Japan Institute of Heterocyclic Chemistry
ISSN:0385-5414
Funders:Swiss National Science Foundation, F. Hoffmann-La Roche & Co. AG, Basel
Permanent URL: https://doi.org/10.5167/uzh-97541

Download

[img]
Preview
Content: Published Version
Language: English
Filetype: PDF
Size: 134kB

TrendTerms

TrendTerms displays relevant terms of the abstract of this publication and related documents on a map. The terms and their relations were extracted from ZORA using word statistics. Their timelines are taken from ZORA as well. The bubble size of a term is proportional to the number of documents where the term occurs. Red, orange, yellow and green colors are used for terms that occur in the current document; red indicates high interlinkedness of a term with other terms, orange, yellow and green decreasing interlinkedness. Blue is used for terms that have a relation with the terms in this document, but occur in other documents.
You can navigate and zoom the map. Mouse-hovering a term displays its timeline, clicking it yields the associated documents.

Author Collaborations