1029-38-5Relevant articles and documents
An Electrochemical Way to Generate Amphiphiles from Hydrazones for the Synthesis of 1,2,4-Triazole Scaffold Cyclic Compounds
Li, Wangyu,Liang, Xiao,Pan, Yuanjiang,Wang, Dungai,Xiong, Mingteng,Zhu, Heping
, (2022/02/02)
An electro-oxidative cyclization pathway in which hydrazones are selected as starting materials to generate amphiphiles by reacting with benzylamines and benzamides was reported. This strategy successfully prepared a series of 1,2,4-triazoles in satisfact
Formation of 1,2,4-Triazoles by Cation Radical Induced Oxidative Addition of Arylhydrazones of Benzaldehyde and Butyraldehyde to Nitriles
Shine, Henry J.,Hoque, A. K. M. Mansurul
, p. 4349 - 4353 (2007/10/02)
1,3,5-Trisubstituted 1,2,4-triazoles have been made in excellent yields by oxidative cycloaddition of arylhydrazones of benzaldehyde and butyraldehyde to aceto-, propio-, and acrylonitrile.Oxidation was achieved with the cation radicals thianthrenyl perchlorate (Th(radical)+ClO4-) and tris(2,4-dibromophenyl)aminium hexachloroantimonate (Ar3N(radical)+SbCl6-).The triazoles thus had a phenyl, p-nitrophenyl, or 2,4-dinitrophenyl group in the 1-position, either a phenyl or propyl group in the 3-position, and a methyl, ethyl, or vinyl group in the 5-position.The formation of 5-vinyltriazoles was confirmed by their hydrogenation to 5-ethyltriazoles, which were obtained also by cycloadditions to propionitrile.New triazoles (eight) were also synthesized by a known alternative route, but in lower yields.The fact that 5-vinyltriazoles were formed instead of 5-cyano-2-pyrazolines shows that cation radical induced cycloadditions do not go through the nitrilimines.Cycloadditions with N-phenylbenzohydrazonoyl chloride and acrylonitrile in the presence of aluminum chloride and of triethylamine were carried out for comparison with the corresponding cation radical reaction.
1,3-DIPOLAR CYCLOADDITIONS INDUCED BY CATION RADICALS. FORMATION OF 1,2,4-TRIAZOLES FROM OXIDATIVE ADDITION OF 1,4-DIPHENYLAZOMETHANE AND ARYL ALDEHYDE PHENYLHYDRAZONES TO NITRILES
Hoque, A. K. M. Mansurul,Kovelesky, Albert C.,Lee, Wang-Keun.,Shine, Henry J.
, p. 5655 - 5658 (2007/10/02)
Reaction of thianthrene cation radical perchlorate .(1+)*ClO4(1-)> with 1,4-diphenylazomethane (DPAM) in MeCN and EtCN led to the formation of 1,2,4-triazoles.Triazole formation is attributed to oxidative cycloaddition of benzaldehyde benzylhydrazone, the tautomer of DPAM, to the solvent nitriles.In confirmation, analogous cycloadditions were achieved by reaction of Th.(1+)*ClO4(1-) with some benzaldehyde phenylhydrazones in the same solvents.