Regioselective alkylation of amino- and mercapto-1,2,4-triazoles with t-BuOH-HClO<sub>4sub>
- 作者：Sergei V. Voitekhovich<sup> ; sup><sup>azole@tut.bysup><sup> ; sup><sup>azole@rambler.rusup> ; Alexander S. Lyakhov ; Ludmila S. Ivashkevich ; Vadim E. Matulis ; Yury V. Grigoriev ; Pavel N. Gaponik ; Oleg A. Ivashkevich
- 关键词：Alkylation ; Acid catalysis ; 1 ; 2 ; 4-Triazoles ; X-ray diffraction
- 刊名：Tetrahedron
- 出版年：2012
- 期刊代码：107_00404020
- 类别：ch
- 出版时间：24 June, 2012
- 卷：68
- 期：25
- 页码：4962-4966
- 文件大小：596 K
摘要
The behavior of amino- and mercapto-1,2,4-triazoles in a t-BuOH-HClO<sub>4sub> system has been examined. Under the investigated conditions monoalkylation of 3-amino-1,2,4-triazole proceeds at the endocyclic N1 atoms whereas 1,2,4-triazole-3-thiol undergoes S-tert-butylation. Exhaustive alkylation of the above mentioned triazoles results in di-tert-butyl substituted derivatives, which give 1,3-disubstituted triazoles under the action of base. 4-Amino-1,2,4-triazole undergoes alkylation on the amino group as well as on the endocyclic N1 atom giving a 1,4-disubstituted triazolium salt. An X-ray diffraction investigation of 5-tert-butylsulfanyl-1,2,4-triazole, 1-tert-butyl-3-tert-butylamino-1,2,4-triazol-4-ium, 1-tert-butyl-3-tert-butylsulfanyl-1,2,4-triazol-4-ium, and 1-tert-butyl-4-tert-butylamino-1,2,4-triazolium perchlorates was carried out.