Specific features of heterocyclization of (E)-3-(2-ethoxypheny1)-1-phenylprop-2-en-1-one with aminoazoles / Ovchinnikova I. G.,Valova M. S.,Matochkina E. G.,Kodess M. I.,Tumashov A. A.,Slepukhin P. A.,Fedorova O. V.,Rusinov G. L.,Charushin V. N. // RUSSIAN CHEMICAL BULLETIN. - 2014. - V. 63, l. 7. - P. 1552-1576.

ISSN/EISSN:

1066-5285 / 1573-9171

Type:

Article

Abstract:

A reaction of 3-(2-ethoxyphenyl)-substituted chalcone with aminoazoles was studied. The nature of aza groups in aminoazoles was found to affect the regioselectivity of beta-amination in the course of the formation of isomeric pyrazolo{[}3,4-b]pyridine, azolo {[}1,5-a] - and {[}4,3-a] pyrimidine systems and the depth of the reaction were determined. A regulatory role of catalysts and solvents in the direction of the cascade reactions was established. Mechanisms of the reactions were suggested. A significance of the alkoxy substituent in chalcone for stereoselective synthesis of Michael adducts, including 3-(2-ethoxypheny1)-3-(7-(2-ethoxypheny1)-5phenyl-6,7-dihydroazolopyrimid in-6-yl)-1-phenylpropan-1-ones, was demonstrated. The structures of products synthesized were established by H-1 and C-13 NMR spectroscopy and X-ray diffraction analysis.

Author keywords:

chalcone; aminoazoles; azolopyrimidines; Michael addition; cascade reactions; catalysis CHALCONE-PODANDS; PHOTOCHEMICAL-TRANSFORMATIONS; DERIVATIVES; CRYSTALS

DOI:

нет данных

Web of Science ID:

ISI:000350878300015

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	JUL
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-9171
Keywords-Plus	CHALCONE-PODANDS; PHOTOCHEMICAL-TRANSFORMATIONS; DERIVATIVES; CRYSTALS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	iov@ios.uran.ru
Funding-Acknowledgement	Russian Federation {[}NSh-505.2012.3]; Ural Branch of the Russian Academy of Sciences {[}12-P-3-1030, 12-T-3-1025]
Funding-Text	This work was financially supported by the Council on Grants at the President of the Russian Federation (Program of State Support for Leading Scientific Schools of the Russian Federation, Grant NSh-505.2012.3) and the Ural Branch of the Russian Academy of Sciences (Project Nos 12-P-3-1030 and 12-T-3-1025).
Number-of-Cited-References	28
Usage-Count-Since-2013	3
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	CD2BJ