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Synthesis 2006(12): 2031-2038  
DOI: 10.1055/s-2006-942391
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Short and Convenient Synthesis of 3-Aminomethyl-5-imino-8-nitro-2,3-dihydroimidazo[1,2-a]pyridines

Sylvia Schmid, Daniel Schühle, Volkhard Austel*
Abteilung Organische Chemie II, Universität Ulm, Albert-Einstein-Allee 11, 89081 Ulm, Germany
e-Mail: volkhard.austel@uni-ulm.de;
Further Information

Publication History

Received 20 January 2006
Publication Date:
11 May 2006 (online)

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Abstract

A two-step synthesis of 3-(N-substituted aminomethyl)-5-(N-substituted imino)-2,3-dihydro-imidazo[1,2-a]pyridines is reported. Starting from 3-bromomethyl-5-chloro-2,3-dihydroimidazo[1,2-a]pyridine, the synthesis comprises two consecutive reactions with primary amines. The products are derived from a three-dimensional molecular scaffold and may therefore be useful in medicinal chemistry in the search for small molecules that can adapt optimally to the three-dimensional binding sites of biological targets. The present synthesis is also particularly suitable for the preparation of combinatorial libraries since primary amines are commercially available in great structural diversity. Moreover, the second step is selective for primary amines, which means that secondary amino groups can be introduced into the products without the need for protection.

Key words

bicyclic compounds - ring opening - amines - combinatorial chemistry - nucleophilic aromatic substitution

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