The First Aminimide Synthesis from Benzoyl Azide and Pyridine

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doi:10.1071/CH07027

The First Aminimide Synthesis from Benzoyl Azide and Pyridine

Ben Capuano ^A, Ian T. Crosby ^A ^C, Edward J. Lloyd ^A, Juliette E. Neve ^A ^B

^A Department of Medicinal Chemistry, Victorian College of Pharmacy, Monash University, Parkville VIC 3052, Australia.
^B Current address: Natural Product Discovery, Eskitis Institute for Cell and Molecular Therapies, Griffith University, Nathan QLD 4111, Australia.
^C Corresponding author. Email: ian.crosby@vcp.monash.edu.au





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Australian Journal of Chemistry 60(3) 214–217 http://dx.doi.org/10.1071/CH07027
Submitted: 29 January 2007 Accepted: 16 February 2007 Published online: 2 April 2007

Abstract

Irradiation of benzoyl azide 1 at 254 nm in the presence of some amines produces aminimides: in the presence of pyridine the aminimide 13 can be isolated in 41% yield; in the presence of N,N-dimethylaniline a CH insertion product 7 is obtained via an intermediate aminimide 12. This is the first reported synthesis of aminimides from a benzoyl azide.