28193-90-0Relevant academic research and scientific papers
Generation of azomethine imine and metal-free formal 1,3-dipolar cycloaddition of imine with PhIO: Reaction, scope, and synthesis
Maiti, Dilip K.,Chatterjee, Nirbhik,Pandit, Palash,Hota, Sandip K.
supporting information; experimental part, p. 2022 - 2024 (2010/09/10)
Generation of azomethine imine and its scope in regioselective 1,3-dipolar cycloaddition (DC) of imine with PhIO toward highly substituted Δ2-1,2,4-triazoline, 1,2,4-triazole, and their fused, chiral, and sugar-based analogues are demonstrated. The Royal Society of Chemistry.
Thermolysis of N-Allylic 1,2,4-Triazoles
Carlsen, Per H. J.,Jorgensen, Kare B.
, p. 797 - 806 (2007/10/03)
A number of 4-allylic substituted 3,5-diphenyl-4H-1,2,4-triazoles were thennolyzed at 315-320° in evacuated glass ampoules. The main reaction in the melt was rearrangement to the corresponding 1-substituted triazoles, which appeared to proceed via competing SN2 and SN2′ mechanisms. The allylic systems were observed to undergo [2,3]-allyl walk reactions between the 1- and 2-ring positions. Allyl to vinyl isomerization also took place. Substitution of the allylic moiety increased the rate of reaction but decreased the rate of isomerization of allylic to the vinylic substituted triazoles. The 4-vinyl substituted triazoles were inert under the reaction conditions. Some triazoles were converted into substituted pyridines. This was proposed to proceed via nitrogen extrusion and formation of a 1,3-dipolar intermediate (nitrile ylide) which added intramolecularly to the allyl moiety and subsequently aromatized to the pyridine.
