Synthesis and alkylation reaction of 1-arylmethyleneamino- and 1-arylsulfonyl-5-hydroxy-1H-1,2,3-triazoles / Rozin YA,Savel'eva EA,Morzherin YY,Dehaen W,Toppet S,Van Meervelt L,Bakulev VA // JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1. - 2002. - V. , l. 2. - P. 211-216.

ISSN/EISSN:

1472-7781 / нет данных

Type:

Article

Abstract:

New derivatives of 1H-1,2,3-triazole 4, 6, 7 were prepared from malonic acid derivatives by a diazo group transfer reaction with p-tosyl azide. It was found that alkylation of sodium 1-aryl-and 1-arylmethyleneamino-1,2,3-triazol-5-olates 7, 4 with methyl iodide, benzyl chloride or substituted phenacyl bromides results in 3-alkyltriazol-3-ium-5-olates 8, 9 that are compounds of mesoionic structure. In contrast, alkylation of 1-arylsulfonyl-substituted triazoles 6 with methyl iodide leads to the 2-methyl-1,2-dihydro-1,2,3-triazol-5-ones 12. Hydrolysis of azomethines 9 affords 1-aminotriazoles 10, which in turn can be deaminated by nitrous acid or butyl nitrite to give 1-alkyl-4-hydroxytriazoles 11.

Author keywords:

нет данных

DOI:

10.1039/b108202g

Web of Science ID:

ISI:000173477500010

Соавторы в МНС:

Другие поля

Поле	Значение
Publisher	ROYAL SOC CHEMISTRY
Address	THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD,, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Language	English
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
ResearcherID-Numbers	Morzherin, Yury/M-7420-2013
ORCID-Numbers	Morzherin, Yury/0000-0002-1333-6676
Number-of-Cited-References	10
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	5
Journal-ISO	J. Chem. Soc.-Perkin Trans. 1
Doc-Delivery-Number	515CH