Transformations of 1,2,4-triazines in reactions with nucleophiles: IV. Nucleophilic substitution of hydrogen in 1,2,4-triazine 4-oxides under acylation conditions / Rusinov VL,Kozhevnikov DN,Kovalev IS,Chupakhin ON,Aleksandrov GG // RUSSIAN JOURNAL OF ORGANIC CHEMISTRY. - 2000. - V. 36, l. 7. - P. 1050-1060.

ISSN/EISSN:

1070-4280 / нет данных

Type:

Article

Abstract:

The reaction of 3-substituted 6-phenyl-1,2,4-triazine derides with aromatic nucleophiles(phenols, indoles, and pyrroles) in the presence of benzoyl chloride yields the corresponding 3,5-disubstituted 6-phenyl-1,2,4-triazines. The mechanism of their formation includes nucleophile addition to protonated 1,2,4-triazine 4-oxide, O-acylation of the sigma (H) adduct, and autoaromatization of the latter. Analogous reactions with 3,5-unsubstituted 1,2,4-triazine 3-oxides show kinetic regioselectivity of the nucleophilic attack at position 5 and thermodynamic regioselectivity of the nucleophile addition at C-3 leading to formation of 6-hydroxy-2,3,6-triazahexatrienes. The reaction of 6-phenyl-1,2P-triazine 4-oxide with indole in acetic anhydride results in formation of the corresponding bis-adduct.

Author keywords:

нет данных

DOI:

нет данных

Web of Science ID:

ISI:000166453600021

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUL
Publisher	MAIK NAUKA/INTERPERIODICA
Address	C/O KLUWER ACADEMIC-PLENUM PUBLISHERS, 233 SPRING ST, NEW YORK, NY 10013-1578 USA
Language	English
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Number-of-Cited-References	13
Usage-Count-Since-2013	1
Journal-ISO	Russ. J. Organ. Chem.
Doc-Delivery-Number	393DH