Tandem A(N)-A(N) reactions in the synthesis of 1H-pyrrolo{[}3,2-e]-1,2,4-triazines and products of their oxidative transformations / Charushin VN,Mochul'skaya NN,Andreiko AA,Kodess MI,Beskrovnyi DV,Litvinov IA,Sinyashin OG,Chupakhin ON // RUSSIAN CHEMICAL BULLETIN. - 2003. - V. 52, l. 8. - P. 1740-1749.

ISSN/EISSN:

1066-5285 / 1573-9171

Type:

Article

Abstract:

The reactions of 3-aryl-1,2,4-triazines with beta-aminovinyl ketones or ethyl beta-amino-crotonates in acetic anhydride at room temperature afforded cyclic products of the tandem nucleophilic addition, viz., 3a,4,7,7a-tetrahydro-1H-pyrrolo{[}3,2-e]-1,2,4-triazines, in good yields. Under oxidative conditions, the latter compounds underwent the pyrrole-ring opening under the action of potassium permanganate to form the corresponding triazinones and were transformed into thriazolyl-substituted pyridines under the action of selenious acid.

Author keywords:

3-aryl-1,2,4-triazines; tandem nucleophilic addition; cyclizations; aminovinyl ketones; ethyl beta-aminocrotonates; pyrrolo{[}3,2-e]-1,2,4-triazines; 5-hydroxy-2-(1H-1,2,4-triazol-1-yl)pyridines DIELS-ALDER REACTIONS; CONDENSED 1,2,4-TRIAZINES; SALTS; CHEMISTRY

DOI:

10.1023/A:1026140218972

Web of Science ID:

ISI:000186446500014

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-9171
Keywords-Plus	DIELS-ALDER REACTIONS; CONDENSED 1,2,4-TRIAZINES; SALTS; CHEMISTRY
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	charushin@prm.uran.ru 7708@mail.ur.ru litvinov@iopc.knc.ru
ResearcherID-Numbers	Sinyashin, Oleg/D-2043-2014 Litvinov, Igor/D-2094-2014
ORCID-Numbers	Sinyashin, Oleg/0000-0002-1708-3143
Number-of-Cited-References	28
Usage-Count-Since-2013	3
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	741EV