ISSN:
1573-9171
Keywords:
gem-dinitro compounds
;
4-nitro-1,2,3-triazoles
;
gem-dinitroethylenes
;
dinitroacetic acid ester
;
N-(β,β-dinitroethyl)-N,N-dialkylamines
;
2,2-dinitroethanol acetate
;
1,1,1-trinitroalkanes
;
nitration
;
cyclization
;
2,4-dinitro-1,2,3-triazole
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract Several chemoselective syntheses have been developed for 4-nitro-1,2,3-triazoles from sodium azide and gem-dinitroethylenes prepared from readily available transformation products of dinitroacetic acid ester: N-(β,β-dinitroethyl)-N,N-dialkylamines, 2,2-dinitroethanol acetate, a mixture of dinitroacetic acid ester with aliphatic aldehydes, or 1,1,1-trinitroalkanes. Hitherto-unknown 4-nitro-5-amino- and 4,5-dinitro-1,2,3-triazoles have been synthesized via successive transformations of the CH3 groups in 5-nitro-4-methyltriazole. Nitration of 4-nitro-1,2,3-triazole with nitronium fluoroborate or acetyl nitrate gave an unknown 2,4-dinitro-1,2,3-triazole.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF01150904