1,2,4-Triazolium Salts from the Reaction of 1-Aza-2-azoniaallene Salts with Nitriles
作者:Quanrui Wang、Johannes C. Jochims、Stefan Köhlbrandt、Lutz Dahlenburg、Mahmound Al-Talib、Atef Hamed、Abd El-Hamid Ismail
DOI:10.1055/s-1992-26206
日期:——
Aryl- and alkylhydrazones 1 of alkyl ketones and propanal are transformed to 1-chloroalkylazo compounds 2 with tert-butyl hypochlorite. Compounds 2 react with antimony(V) chloride or aluminum(III) chloride to give 1-aza-2-azoniaallene salts 3 as reactive intermediates, which are intercepted as 3H-1,2,4-triazolium salts 5 with nitriles. In most cases these salts rearrange spontaneously to form the corresponding 1H-triazolium salts 6. Benzophenone arylhydrazone 1x reacts with tert-butyl hypochlorite and antimony(V) chloride to furnish the 1-aryl-3-phenylindazolium salt 7. An X-ray diffraction analysis of a 1H-1,2,4-triazolium salt [6,7,8,9- tetrahydro-2-methyl-3-(2,4,6-trichlorophenyl)-5H-[1,2,4] triazolo [5,1-a]azepinium hexachloroantimonate (6n)] is reported.
芳香族和烷基肼酮的烷基酮和丙醛的肼酮 1 与叔丁基次氯酸盐反应转化为1-氯烷基偶氮化合物 2。化合物 2 与五氯化锑或三氯化铝反应生成活性中间体 1-氮-2-氮阳离子盐 3,这些中间体与腈类化合物反应形成3H-1,2,4-三唑鎓盐 5。在大多数情况下,这些盐自发重排形成相应的1H-三唑鎓盐 6。苯酮芳香族肼酮 1x 与叔丁基次氯酸盐和五氯化锑反应生成1-芳基-3-苯基吲哚鎓盐 7。报告了一种1H-1,2,4-三唑鎓盐 [6,7,8,9-四氢-2-甲基-3-(2,4,6-三氯苯基)-5H-[1,2,4]三唑[5,1-a]氮杂七元环六氯锑酸盐(6n)] 的X射线衍射分析。