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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
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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.

Key words

3-methoxalylchromone - 5-aminoimidazoles - imidazo[4,5-b]pyridines - 1-desazapurines - cyclocondensations

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21

Crystallographic data (excluding structure factors) for the structures of 7a and 9b, reported in this paper, have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 799366 for 7a and CCDC 799367 for 9b. These data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44 (1223)336033; E-mail: deposit@ccdc.cam.ac.uk, or via www.ccdc.cam.ac.uk/data_request/cif

22

Iaroshenko, V. O.; Mkrtchyan, S.; Ghazaryan, G.; Hakopyan, A.; Maalik, A.; Supe, L.; Ostrovskyi, D.; Villinger, A.; Tolmachev, A.; Sosnovskikh, V. Ya.; Langer, P. manuscript in preparation.