ChemInform Abstract: ALKYLATION OF 3‐R‐1,2,4‐TRIAZOLES BY ACTIVATED HALOALKANES

A new method for the synthesis of n-(2-aminoethyl)azoles by alkylation of azoles with 2-alkyl-4,5-dihydrooxazoles

“…11 The resulting nitriles were hydrogenated in an autoclave (70-90 °C, 100 atm, Raney nickel) in the presence of excess ammo nia, by analogy with a known synthesis of azolylpropyl amines. 6 However, final column chromatography gave only secondary N,N bis(2 azolylethyl)amines.…”

Linking polynitro hexaazaisowurtzitane cagesviaanN,N'-methylene bridge: a promising strategy for designing energetic ensembles of CL-20 derivatives and adjusting their properties

“…Quite recently, as part of our systematic research into the synthesis and properties of energetic hexaazaisowurtzitanes, 9 we obtained the first representative of this class of cage compounds with an alkyl-nitramine bridge, and revealed the positive effect of such a structural transformation. 9 a The theoretical calculations reported in the literature 10 show considerable promise for the binding of CL-20 clusters via the N , N ′-methylene bridge, which was previously used widely for the functionalization of azoles, and various energetic methylene-linked derivatives have been obtained 11 (Scheme 1).…”

Reactions of 3-nitro-1,2,4-triazole derivatives with alkylating agents. 8*. Alkylation of 3-nitro-5-R-1,2,4-triazoles with derivatives of diethylene glycol in the presence of alkali

“…In the second case as a result of the polymeric nature of the electrophilic reagent and linked with this, the steric hindrance towards attack at the N(2)-heterocycle position, a reduction of 20-22% occurs in the fraction of the products of N(2) substitution compared with the use of low-molecular agents [9]. Alkylation of NRT in neutral media [10] with dimethyl sulfate occurs at each of the three atoms N(1), N (2), and N(4) of the heterocycle with preferential formation of substitution products at the N(4) atom and products of their further conversion, viz. 1,4-di-and 1,4,5-trimethyl-3-nitro-1,2,4-triazolium salts and 1,4-di-, 1,3,4-trimethyl-1,2,4-triazol-5-ones.…”

“…These were N(1),N'(1), N(1),N' (2), and N(2),N'(2) isomeric nitrotriazole derivatives respectively of bis[2-(3-nitro-1,2,4-triazol-1-yl)ethyl] ether (5a), 3-nitro-1-{2-[2'-(5'-nitro-1',2',4'-triazol-1'-yl)ethoxy]ethyl}-1,2,4-triazole (5b), and bis[2-(5-nitro-1,2,4-triazol-1-yl)ethyl] ether (5c).…”

“…The N(1),N'(1) isomeric NRT derivatives are of interest not only in connection with the display of selectivity of their formation, but also as starting materials for the directed synthesis of salts of nitrotriazoles 1 and 2, since of all N(1), N (2), and N(4) alkyl-substituted NRT only the N(1) isomer provides a selective synthesis of stable 1,4-di-and 1,4,5-trisubstituted 3-nitro-1,2,4-triazolium salts [10,11,14].…”