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Synthesis 2010(10): 1692-1696  
DOI: 10.1055/s-0029-1218739
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Imidazo[1,2]hetarylglyoxylates: Synthesis and Reactivity toward Nucleophiles

Irina A. Zamkovaa, Oleksiy O. Chekotyloa, Oleksandr V. Geraschenkoa,b, Oleksandr O. Grygorenko*a,b, Pavel K. Mykhailiuk*a,b, Andrey A. Tolmacheva,b
a Enamine Ltd., Oleksandra Matrosova Street 23, Kyiv 01103, Ukraine
b Department of Chemistry, Kyiv National Taras Shevchenko University, Volodymyrska Street 64, Kyiv 01033, Ukraine
Fax: +380(44)2351273; e-Mail: gregor@univ.kiev.ua; e-Mail: pashamk@gmx.de;
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Publikationsverlauf

Received 3 February 2010
Publikationsdatum:
15. April 2010 (online)

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Abstract

A practical approach to imidazo[1,2]hetarylglyoxylates via Friedel-Crafts acylation of the parent fused imidazoles with ethyl oxalyl chloride is reported. The reaction is strongly influenced by the electron-donating properties of the starting heterocycle. The generated imidazo[1,2]hetarylglyoxylates undergo standard transformations typical of α-keto esters upon reaction with various nucleophiles. All the products contain an imidazoheterocyclic scaffold which is considered a privileged structure for drug discovery.

Key words

imidazoheterocycles - acylation - glyoxylates - privileged scaffolds

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