Synthesis of nitro, nitroso, azo, and azido derivatives of (4-R1-5-R2-1,2,3-triazol-1-yl)-1,2,5-oxadiazoles by oxidation and diazotization of the corresponding amines

Abstract

Nitro , nitroso , and azo 1,2,5 oxadiazoles with 4 R 1 5 R 2 1,2,3 triazol 1 yl substituents were synthesized by oxidation of amino (1,2,3 triazol 1 yl) 1,2,5 oxadiazoles (aminotri azolylfurazans). Azido 1,2,5 oxadiazole was prepared by diazotization of amino(triazo lyl)furazan followed by treatment of the diazonium salt with sodium azide. Depending on the nature of the substituents and the reagent, triazolylfurazans can undergo destruction to give amino R furazans (R = NO 2 , N 3 , aminofurazanylazo), the amino group being formed from the triazole ring.

Synthesis and characterization of polyhedral oligomeric azido‐octaphenylsilsesquioxane

“…The preparation of aryl azide relies on a rather limited selection of transformations 11. They can be prepared from the corresponding amines via their diazonium salts,18–20 or from the corresponding amines using triflyl azide 10, 21, 22. However, the preparation of the triflyl azide in the solvent CH 2 Cl 2 is a risky undertaking because the nucleophilic substitution on CH 2 Cl 2 , leading to azido‐chloromethane and/or diazidomethane, can result in explosion.…”

Synthesis and transformations of 4-amino-4′-(4-nitro-1H-1,2,3-tri-azol-1-yl)- and 4-amino-4′-(1,2,3-triazolo[4,5-c]-1,2,5-oxadiazol-5-yl)- 3,3′-(NNO)-azoxy-1,2,5-oxadiazoles

“…Derivatives of the furazan series, having in the molecule an azoxy group and, at least, one 1H 1,2,3 triazol 1 yl substituent at tached to the furazan ring (as in compounds 1), as well as the structure, which would have combine this or 1,2,3 triazolo[4,5 c]furazan 5 yl substituents, azo and azoxy groups (as in compounds 2), have not been described before our investigations. Earlier, 5 we tried to obtain azoxyfurazan 3 with two identical 1,2,3 triazolyl sub stituents by the oxidation of amino(triazolyl)furazan 1a with the mixtures on the basis of hydrogen peroxide, however, these experiments did not lead to the target compound (Scheme 1).…”

Nucleophilic substitution in the series of (1,2,3-triazol-1-yl)-1,2,5-oxadiazoles. Reactions with N-, O-, and S-nucleophiles

“…Some reactions of these compounds (e.g., oxida tion of the NH 2 group at the furazan ring into NO 2 , NO, and N=N groups and transformation of the NH 2 group into an N 3 group via diazotization) were investigated. 12 The first example of nucleophilic substitution in tri azolylfurazans was displacement of the nitro group at the furazan ring in 4 nitro 3 (4 phenyl 1H 1,2,3 triazol 1 yl) 1,2,5 oxadiazole by an amino group in a reaction with morpholine. 12 Recently, 13 new representatives of triazolylfurazans have been obtained by reactions of aminoazidofurazan with ethyl chloroacetoacetate, also with the use of N nucleophiles such as hydrazine and secondary amines (dimethylamine, diethylamine, isobutylamine, pyrro lidine, and piperidine).…”

“…12 The first example of nucleophilic substitution in tri azolylfurazans was displacement of the nitro group at the furazan ring in 4 nitro 3 (4 phenyl 1H 1,2,3 triazol 1 yl) 1,2,5 oxadiazole by an amino group in a reaction with morpholine. 12 Recently, 13 new representatives of triazolylfurazans have been obtained by reactions of aminoazidofurazan with ethyl chloroacetoacetate, also with the use of N nucleophiles such as hydrazine and secondary amines (dimethylamine, diethylamine, isobutylamine, pyrro lidine, and piperidine). Information on the preparation of the starting chloromethyl substrate in the individual state and its physicochemical characteristics are lacking.…”

“…Nitro compounds 1a,b and 2c and chloromethyl de rivatives 2a,b have been synthesized earlier. 8,9,12 Tri azolylfurazans 3a-c and 4 have not been described. The synthesis of chlorides 2a,b by cycloaddition of 4 amino 3 azidofurazan (5) to propargyl chloride 8 allowed only one isomer (2a) to be isolated in good yield; for this reason, we employed here an alternative method of pre paring compound 2b.…”