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Synlett 2005(14): 2214-2218  
DOI: 10.1055/s-2005-872249
LETTER
© Georg Thieme Verlag Stuttgart · New York

Acid-Mediated Amine Exchange of N,N-Dimethylformamidines: Preparation of Electron-Rich Formamidines

David D. Díaz, Warren G. Lewis, M. G. Finn*
Department of Chemistry and The Skaggs Institute for Chemical Biology, The Scripps Research Institute, 10550 N. Torrey Pines Rd., La Jolla, CA 92037, USA
Fax: +1(858)7848850; e-Mail: mgfinn@scripps.edu;
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Publication History

Received 24 March 2005
Publication Date:
26 July 2005 (online)

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Abstract

The effect of acid in the amine exchange of N,N-dimethylformamidines has been revisited, allowing the preparation of highly electron-rich compounds that are difficult to obtain under standard conditions. The use of propargylamine as nucleophile led to the formation of substituted imidazoles.

Key words

formamidine - acid - amine exchange - imidazole

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