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Synthesis 2011(3): 469-479  
DOI: 10.1055/s-0030-1258364
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

3-(Dichloroacetyl)chromone; A New Building Block for the Synthesis of Formylated Purine Isosteres: Design and Synthesis of Fused α-(Formyl)pyridines

Viktor O. Iaroshenko*a,b, Satenik Mkrtchyana, Gagik Ghazaryana,c, Ani Hakobyana,c, Aneela Maalika, Linda Supea, Alexander Villingera, Andrei Tolmachevb,d, Dmytro Ostrovskyia, Vyacheslav Ya. Sosnovskikhe, Tariel V. Ghochikyanc, Peter Langer*a,f
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
Fax: +380(44)5373253; e-Mail: yaroshenko@enamine.net;
c Faculty of Chemistry, Yerevan State University, Alex Manoogian 1, 0025 Yerevan, Armenia
d Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
e Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation
f Leibniz-Institut für Katalyse e. V. an der Universität Rostock, Albert-Einstein-Str. 29a, 18059 Rostock, Germany
Further Information

Publication History

Received 21 October 2010
Publication Date:
15 December 2010 (online)

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Abstract

The first synthesis of 3-(dichloroacetyl)chromone from 3-(dimethylamino)-1-(2-hydroxyphenyl)propen-1-one and dichloroacetyl chloride is described. The reaction of electron-rich aminoheterocycles with 3-(dichloroacetyl)chromone provides a set of diverse fused pyridines bearing the CHCl2-substituent at the α-position of the pyridine core. Subsequent hydrolysis leads to the formation of annulated α-(formyl)pyridines.

Key words

3-(dichloroacetyl)chromone - 4H-1-benzopyran-4-one - heterocyclic amines - fused pyridines - annulation reactions

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13

Crystallographic data (excluding structure factors) for the structure 15a, 16, 23b, and 24g, reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication No. 801470 for 15a, 801471 for 16, 801472 for 23b, and 801473 for 24g, 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.