Synthesis of heteroannulated 3-nitro- and 3-aminopyridines by cyclocondensation of electron-rich aminoheterocycles with 3-nitrochromone / Iaroshenko Viktor O.,Mkrtchyan Satenik,Gevorgyan Ashot,Vilches-Herrera Marcelo,Sevenard Dmitri V.,Villinger Alexander,Ghochikyan Tariel V.,Saghiyan Ashot,Sosnovskikh Vyacheslav Ya,Langer Peter // TETRAHEDRON. - 2012. - V. 68, l. 11. - P. 2532-2543.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

3-Nitrochromone reacts with electron-rich aminoheterocycles (in glacial acetic acid at reflux) and anilines (in a mixture of DMF and TMSCI at 100-140 degrees C) to give a variety of hetero(carbo)annulated 3-nitropyridines. The reaction, involving a formal {[}3+3] cyclocondensation, proceeds in high yields and appears not to be influences greatly by the nature of the 1,3-C,N-dinucleophile as seen from the thorough scope study. The synthetic utility of the products was demonstrated by their conversion into the corresponding 3-aminopyridine derivatives. An NMR study and X-ray crystallographic analysis are reported. (C) 2011 Elsevier Ltd. All rights reserved.

Author keywords:

Chromones; Cyclocondensation; Aminoheterocycles; Anilines; Purine isosteres; Regioselectivity 3-SUBSTITUTED CHROMONES; EFFICIENT SYNTHESIS; KINASE INHIBITORS; CYTOTOXIC AGENTS; ANTITUMOR AGENTS; METHOXIDE ION; DERIVATIVES; PYRIDINES; 3-(POLYFLUOROACYL)CHROMONES; NUCLEOPHILES

DOI:

10.1016/j.tet.2011.06.101

Web of Science ID:

ISI:000301692500012

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	MAR 18
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	3-SUBSTITUTED CHROMONES; EFFICIENT SYNTHESIS; KINASE INHIBITORS; CYTOTOXIC AGENTS; ANTITUMOR AGENTS; METHOXIDE ION; DERIVATIVES; PYRIDINES; 3-(POLYFLUOROACYL)CHROMONES; NUCLEOPHILES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	viktor.iaroshenko@uni-rostock.de peter.langer@uni-rostock.de
ORCID-Numbers	Vilches Herrera, Marcelo/0000-0001-8282-8650
Number-of-Cited-References	76
Usage-Count-Since-2013	14
Journal-ISO	Tetrahedron
Doc-Delivery-Number	911BO