Synthesis 2011(1): 133-141  
DOI: 10.1055/s-0030-1258339
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

3-Methoxalylchromone - A Versatile Reagent for the Regioselective Synthesis of 1-Desazapurine

Dmytro Ostrovskyia, Viktor O. Iaroshenko*a,b,c, Iftikhar Alia, Satenik Mkrtchyana, Alexander Villingera, Andrei Tolmachevb,c, Peter Langer*a,d
a Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany
Fax: +49(381)4986412; e-Mail: viktor.iaroshenko@uni-rostock.de; e-Mail: iva108@googlemail.com;
b National Taras Shevchenko University, 62 Volodymyrska st., Kyiv-33, 01033, Ukraine
c ‘Enamine Ltd.’, 23 A. Matrosova st., 01103 Kyiv, Ukraine
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net ;
d Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Further Information

Publication History

Received 7 October 2010
Publication Date:
26 November 2010 (online)

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Abstract

The reaction of 5-amino-1H-imidazoles with 3-methoxalylchromone provided a set of imidazo[4,5-b]pyridines (1-des­azapurines) bearing the CO2Me substituent at the α-position of the pyridine core. The corresponding acids were synthesized by subsequent hydrolysis of the ester function. Being typical purine isos­teres, 1-desazapurines are considered to be potent pharmacophores, and are widely used in drug design and medicinal chemistry.