22244-55-9Relevant academic research and scientific papers
Reactions of 3-azido-1,2,4-triazole with electrophiles
Kofman,Krasnov
, p. 1651 - 1656 (2004)
Alkylation of 3-azido-1,2,4-triazole with oxiranes, bromoacetone, and methyl vinyl ketone furnished a mixture of N-substituted 3- and 5-azido-1,2,4-triazoles, 3-azido compounds prevailing. The same substrate subjected to heterylation with 3,5-dinitro-1,2,4-triazole derivatives reacted selectively at the N1 atom, and its bromination afforded 3-azido-5-bromo-1,2,4-triazole. 2004 MAIK Nauka/ Interperiodica .
Heterylation of 3-R1-5-R2-1,2,4-triazoles with derivatives of 3,5-dinitro-1,2,4-triazole
Kofman
, p. 1158 - 1168 (2007/10/03)
Heterylation of 3-R1-5-R2-1,2,4-triazoles (pKa 3-12) with N-alkyl-, N-alkenyl-, N-alkoxycarbonyl-, N-oxoalkyl-, N-nitroxyalkyl, and N-nitroaminoalkyl-3,5-dinitro-1,2,4-triazoles results in substitution of a nitro group in 5 position of the dinitro compound yielding 1-R-methyl-3-nitro-5-(3-R1-5-R 2-1,2,4-triazolyl)-1,2,4-triazoles. The side processes: Hydroxide-ion attack on C5 and (or) N1 of the ring both in the substrate and in the target compound afford 1-R-methyl3-nitro-1,2,4-triazol-5-ones, 3,5-dinitro-1,2,4-triazole and NH-acids of N-C-bitriazole series. Optimal reaction media are aprotic dipolar substances, and for compounds prone to heterolysis ethyl acetate-water systems. The azole pKa is the decisive factor controlling the composition and the ratio of reaction products. The process is promising for azoles with pKa > 5, and the optimal range of pKa is 8-10.
Synthesis of novel derivatives of 3(5)-alkylsulfonyl-1,2,4-triazoles
Tolstyakov,Pevzner,Tselinskii
, p. 1458 - 1465 (2007/10/03)
The feasibility of preparing novel 1,2,4-triazole derivatives bearing alkylsulfonyl and other functional groups on the ring carbon atom has been demonstrated. The syntheses are carried out via transformation of the amino group of 3(5)-alkylsulfonyl-5(3)-amino-1,2,4-triazoles into other functional groups.
HETEROCYCLIC NITRO COMPOUNDS. 26. REACTION OF 1-SUBSTITUTED 3,5-DINITRO-1,2,4-TRIAZOLES WITH ANIONS OF HETEROCYCLIC NH ACIDS
Pevzner, M. S.,Koffman, T. P.,Kibasova, E. N.,Sushchenko, L. F.,Uspenskaya, T. L.
, p. 194 - 199 (2007/10/02)
1-Substituted 3-nitro-5-(N-azolyl)-1,2,4-triazoles mixed with 1-substituted 3-nitro-1,2,4-triazol-5-ones are obtained in the reaction of 1-substituted 3,5-dinitro-1,2,4-triazoles with anions of heterocyclic NH acids (1,2,4-triazole, 1,2,3-triazole, pyrazole, benzotriazole, and indazole derivatives). 1-Methyl-3-nitro-5-amino-1,2,4-triazole is formed instead of the expected 5-tetrazolyl derivative in the reaction of 1-methyl-3,5-dinitro-1,2,4-triazole with tetrazole in alkaline media.
METHYLATION OF 3-NITRO-1,2,4-TRIAZOL-5-ONE
Kofman, T. P.,Pevzner, M. S.,Zhukova, L. N.,Kravchenko, T. A.,Frolova, G. M.
, p. 375 - 378 (2007/10/02)
The methylation of 3-nitro-1,2,4-triazol-5-one with dimethyl sulfate in an alkaline medium is unselective at both substitution steps and occurs at the N1 and N4 atoms of the ring and the oxygen of the oxo group.The degree of conversion (mono- or disubstitution) and the isomeric composition of the alkylation products depend on the reactivity of the nucleophilic centers and on the reaction conditions (the ratio of the reagents, the pH of the medium, and the solvent).The UV spectra were investigated and the pKa values were determined for 3-nitro-1,2,4-triazol-5-one and its monomethyl derivatives.The first step in the dissociation of 3-nitro-1,2,4-triazol-5-one is removal of the proton from the N4 atom, and this determines the preferential methylation at this center in the monoanion.In the dianion susbtitution at the more nuclephilic heteratom N1 predominates.
