Effect of substituent in pyridine-2-carbaldehydes on their heterocyclization to 1,2,4-triazines and 1,2,4-triazine 4-oxides / Krinochkin A. P.,Kopchuk D. S.,Chepchugov N. V.,Kovalev I. S.,Zyryanov G. V.,Rusinov V. L.,Chupakhin O. N. // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2017. - V. 53, l. 7. - P. 963-970.

ISSN/EISSN:

1070-4280 / 1608-3393

Type:

Article

Abstract:

A series of substituted pyridine-2-carbaldehydes were brought into heterocyclization with isonitrosoacetophenone hydrazones, followed by aromatization by the action of oxidants or by dehydration in boiling acetic acid. As a result, substituted 3-(pyridin-2-yl)-1,2,4-triazines or 3-(pyridin-2-yl)-1,2,4-triazine 4-oxides were formed. 6-Formylpyridine-2-carbonitrile failed to undergo heterocyclization, 6-methylpyridine-2-carbaldehyde and methyl 6-formylpyridine-3-carboxylate can be converted to both 1,2,4-triazine and 1,2,4-triazine 4-oxide derivative, and only 1,2,4-triazine 4 oxides were obtained from 6-bromopyridine-2-carbaldehyde and 6-formyl-3-phenylpyridine-2-carbonitrile. Convenient procedures were proposed for the synthesis of some initial pyridinecarbaldehydes.

Author keywords:

DIELS-ALDER REACTION; PHOTOPHYSICAL PROPERTIES; 2,2'-BIPYRIDINE; COMPLEXES; DERIVATIVES; STRATEGY

DOI:

10.1134/S1070428017070016

Web of Science ID:

ISI:000408707900001

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL
Publisher	MAIK NAUKA/INTERPERIODICA/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
EISSN	1608-3393
Keywords-Plus	DIELS-ALDER REACTION; PHOTOPHYSICAL PROPERTIES; 2,2'-BIPYRIDINE; COMPLEXES; DERIVATIVES; STRATEGY
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	gvzyryanov@gmail.com
Funding-Acknowledgement	Russian Science Foundation {[}15-13-10 033]; Council for Grants at the Russian Federation {[}MK-644.2017.3]; Government of the Russian Federation {[}211, 02.A03.21.0006]
Funding-Text	This study was performed under financial support by the Russian Science Foundation (project no. 15-13-10 033), by the Council for Grants at the President of the Russian Federation (project no. MK-644.2017.3), and by the Government of the Russian Federation (Program no. 211, contract no. 02.A03.21.0006).
Number-of-Cited-References	29
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	1
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	FF2DK