From 3-chloromethyl-1,2,4-triazine4-oxides to various substituted pyridines and 1,2,4-triazines / Kozhevnikov VN,Kozhevnikov DN,Shabunina OV,Kataeva NN,Yushchuk SA,Rusinov VL,Chupakhin ON // RUSSIAN CHEMICAL BULLETIN. - 2005. - V. 54, l. 9. - P. 2187-2196.

ISSN/EISSN:

1066-5285 / нет данных

Type:

Article

Abstract:

An efficient strategy for the synthesis of new pyridine and 1,2,4-triazine derivatives starting from available 6-aryl-3-chloromethyl-1,2,4-triazine 4-oxides was proposed. The deoxygenative nucleophilic hydrogen substitution in the triazine-oxide ring, nucleophilic Substitution of the chlorine atom in the side chain, and transformations of the 1,2,4-triazine ring into the pyridine ring via the inverse-electron-demand Diels-Alder reactions, being used in different orders, are a rather flexible tool for the functionalization of the titled heterocycles. The cyanide anion, indoles, thiophenols, amines, and triphenylphosphine were used as nucleophiles. The direct introduction of indole residues into the 1,2,4-triazine ring followed by the substitution of the chlorine atom by a residue of the primary or secondary aliphatic amine was found to be the most convenient method for the library synthesis.

Author keywords:

pyridine; indole; 1,2,4-triazine; nucleophilic substitution; inverse-electron-demand Diels-Alder reaction; Wittig reaction NUCLEOPHILIC-SUBSTITUTION; 4-OXIDES; TRANSFORMATIONS; CATALYSIS; HYDROGEN; ROUTE

DOI:

10.1007/s11172-006-0095-4

Web of Science ID:

ISI:000236859600026

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP
Publisher	CONSULTANTS BUREAU/SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	NUCLEOPHILIC-SUBSTITUTION; 4-OXIDES; TRANSFORMATIONS; CATALYSIS; HYDROGEN; ROUTE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	dnk@htf.ustu.ru
ResearcherID-Numbers	Kozhevnikov, Valery/B-1178-2010
ORCID-Numbers	Kozhevnikov, Valery/0000-0001-7032-8886
Number-of-Cited-References	24
Usage-Count-Since-2013	1
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	033OY