3-Formylchromones, Acylpyruvates,
and Chalcone as Valuable Substrates for the Syntheses of Fused Pyridines

Viktor O. Iaroshenko; Satenik Mkrtchyan; Dmitriy M. Volochnyuk; Peter Langer; Vyacheslav Ya. Sosnovskikh; Dmytro Ostrovskyi; Sergii Dudkin; Anton V. Kotljarov; Mariia Miliutina; Iryna Savych; Andrei A. Tolmachev

doi:10.1055/s-0029-1218842

PAPER

3-Formylchromones, Acylpyruvates, and Chalcone as Valuable Substrates for the Syntheses of Fused Pyridines

Viktor O. Iaroshenko*^a,b, Satenik Mkrtchyan^b, Dmitriy M. Volochnyuk^a,c, Peter Langer*^b, Vyacheslav Ya. Sosnovskikh*^d, Dmytro Ostrovskyi^a, Sergii Dudkin^b, Anton V. Kotljarov^e, Mariia Miliutina^f, Iryna Savych^f, Andrei A. Tolmachev^a,c
^a National Taras Shevchenko University, 62 Volodymyrska St., Kyiv-33, 01033, Ukraine
^b 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@gmail.com;
^c Enamine Ltd., 23 A. Matrosova st., 01103 Kyiv, Ukraine
^d Department of Chemistry, Ural State University, 51 Lenina Ave., 620083 Ekaterinburg, Russian Federation
e-Mail: vyacheslav.sosnovskikh@usu.ru;
^e Institute of Organic and Bioorganic Chemistry, University of Tartu, Jakobi 2, 51014 Tartu, Estonia
^f Organic Chemistry Department, National Kharkiv V. N. Karazin University, sq. Svobody 4, Kharkiv-77, 61077, Ukraine

Abstract

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Abstract

The reaction of electron-rich aminoheterocycles with 1,3-CCC-dielectrophiles, such as 3-formylchromones, acylpyruvates, and chalcone, provided diversely fused pyridines. Starting from 5-amino-1-(2,3-O-isopropylidene-β-d-ribofuranosyl)-1H-pyrazole, nucleosides containing a pyrazolo[3,4-b]pyridine fragment were obtained, which can be considered as adenosine deaminase (ADA) inhibitors.

Key words

aminoheterocycles - 3-formylchromones - acylpyruvates - chalcone - fused pyridines - annulation reaction - nucleosides

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