Synthesis and properties of 5-hydroxy-1-tolyl(benzyl)-1,2,3-triazoles / Nein Yulia I.,Glukhareva Tatiana V.,Sadovskova Ksenia A.,Morzherin Yuri Yu. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2016. - V. 52, l. 9. - P. 716-720.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

1-Benzyl-N-tolyl-1,2,3-triazole-4-carboxamide was accessed via rearrangement of N-benzyl-1-tolyl-1,2,3-triazole-4-carboxamide. It is shown that by boiling in various solvents an equilibrium between isomeric triazoles and diazomalondiamides is established, and that the equilibrium is shifted toward 1-benzyl-1,2,3-triazole. The two isomeric triazoles are shown to undergo alkylation reactions. For 5-hydroxy-1-tolyl-1,2,3-triazole, the alkylation occurs at position 3 of the heterocycle to form a mesoionic triazol-5-olate, whereas for 1-benzyl-5-hydroxy-1,2,3-triazole, alkylation leads to the formation of a 5-alkoxy derivative.

Author keywords:

diazo compound; mesoionic heterocycles; 1,2,3-triazole; alkylation; pericyclic reactions; rearrangement SUBSTITUTED 4-HYDROXY-1,2,3-TRIAZOLES; DERIVATIVES

DOI:

10.1007/s10593-016-1953-0

Web of Science ID:

ISI:000388588400014

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	SUBSTITUTED 4-HYDROXY-1,2,3-TRIAZOLES; DERIVATIVES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	yu.yu.morzherin@urfu.ru
ResearcherID-Numbers	Nein, Juliya/P-4340-2016
ORCID-Numbers	Nein, Juliya/0000-0003-0569-5713
Funding-Acknowledgement	Ministry of Education and Science of the Russian Federation {[}4.560.2014-K]; Russian Federation Government {[}211, 02.A03.21.0006]
Funding-Text	The study was performed within the framework of completing the State assignment of the Ministry of Education and Science of the Russian Federation No 4.560.2014-K, with the financial support of the Russian Federation Government directive No 211 (contract number 02.A03.21.0006).
Number-of-Cited-References	41
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	2
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	ED1EV