105958-58-5Relevant academic research and scientific papers
Michael-type addition of azoles of broad-scale acidity to methyl acrylate
Boncel, Slawomir,Saletra, Kinga,Hefczyc, Barbara,Walczak, Krzysztof Z.
supporting information; experimental part, p. 173 - 178 (2011/05/19)
An optimisation of Michael-type addition of azole derivatives of broad-scale acidity - ranging from 5.20 to 15.00 pKa units - namely 4-nitropyrazole, 3,5-dimethyl-4-nitropyrazole, 4(5)-nitroimidazole, 4,5-diphenylimidazole, 4,5-dicyanoimidazole, 2-methyl-
3-NITRO-5-R-1,2,4-TRIAZOL-1-YLPROPIONIC ACIDS AND THEIR DERIVATIVES
Kofman, T. P.,Krivosheeva, G. S.,Pevzner, M. S.
, p. 1913 - 1918 (2007/10/02)
The reaction of 3-nitro-5-R-1,2,4-triazoles with acrylic acid and its derivatives and the subsequent transformations of the addition products give 3-nitro-5-R-1,2,4-triazol-1-ylpropionic acids, their esters, and their nitriles.It was noticed that the strongest of the NH acids of the series 3,5-dinitro-1,2,4-triazole (pKa -0.66) had anomalously high reactivity in reactions of the Michael type in comparison with compounds of moderate acidity (pKa 3-7).The latter exhibit the usual increase in reactivity with increase in the pKa value.The structure was modified byheteroaryl substitution with triazolate anions at position 5 in 3,5-dinitro-1,2,4-triazol-1-ylpropionic ester.
