Alkylation of 4(5)-nitro-1,2,3-triazole with alcohols in strongly acidic media

Alkylation of 4(5)-nitro-1,2,3-triazole with alcohols in concentrated H 2 SO 4 occurs at all three endocyclic N atoms, giving a mixture of isomeric N (1)-, N (2)-, and N (3)-alkyl-4-nitro-1,2,3-triazoles (alkyl is isopropyl, sec -butyl, and cyclohexyl). The selectivity of the alkylation depends on t...

Full description

Saved in:
Bibliographic Details
Published in:Russian chemical bulletin 2013, Vol.62 (1), p.111-116
Main Authors: Sakovich, G. V., Sukhanov, G. T., Filippova, Yu. V., Sukhanova, A. G., Bosov, K. K.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Full Articles
Inorganic Chemistry
Organic Chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Alkylation of 4(5)-nitro-1,2,3-triazole with alcohols in concentrated H 2 SO 4 occurs at all three endocyclic N atoms, giving a mixture of isomeric N (1)-, N (2)-, and N (3)-alkyl-4-nitro-1,2,3-triazoles (alkyl is isopropyl, sec -butyl, and cyclohexyl). The selectivity of the alkylation depends on the alcohol used. The most selective alkylation is provided at the N(2) atom when isopropyl (81%) and sec -butyl alcohols are used (67%). With an increase in the reaction time, also in the order isopropyl-, sec -butyl-, and cyclohexyl-4-nitro-1,2,3-triazoles, the N(2)-isomers undergo isomerization into N (1)-alkyl-4-nitro-1,2,3-triazoles. In all the cases, the fraction of the N(3)-substitution products in the mixtures is 6–30%.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-013-0016-2