A Novel Approach to Substituted 2H-Azirines

2-(Benzotriazol-1-yl)-2H-azirines 4a−c, obtained by treatment of oximes 2a−c with tosyl chloride and aqueous KOH, were reacted with benzylmagnesium bromide or 4-methylbenzylmagnesium bromide in the presence of zinc chloride to give 2-benzyl-2H-azirines 5a−f. Potassium phthalimide and sodium salt of...

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Bibliographic Details
Published in:Journal of organic chemistry 2003-11, Vol.68 (23), p.9105-9108
Main Authors: Katritzky, Alan R, Wang, Mingyi, Wilkerson, Chavon R, Yang, Hongfang
Format: Article
Language:English
Subjects:
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
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Summary:2-(Benzotriazol-1-yl)-2H-azirines 4a−c, obtained by treatment of oximes 2a−c with tosyl chloride and aqueous KOH, were reacted with benzylmagnesium bromide or 4-methylbenzylmagnesium bromide in the presence of zinc chloride to give 2-benzyl-2H-azirines 5a−f. Potassium phthalimide and sodium salt of benzenethiol converted 2-(benzotriazol-1-yl)-2H-azirines 4a−c into novel 2H-azirines 6a−c and 7 in good yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo034472i