Centre for Catalysis Research and Innovation, Department of Chemistry and Biomolecular Sciences, University of Ottawa , 10 Marie Curie, Ottawa, Ontario K1N 6N5, Canada.
Org Lett. 2016 Aug 5;18(15):3778-81. doi: 10.1021/acs.orglett.6b01788. Epub 2016 Jul 26.
Various nitrogen-substituted iso(thio)cyanates engage in [3 + 2]-cycloaddition reactions to form azomethine imines containing triazolone, triazole-thione, and pyrazole-thione cores. First, iminoisothiocyanates are shown to undergo aminothiocarbonylation reactions with strained alkenes, and a comparison with recently reported reactions of iminoisocyanates highlights their reduced reactivity. In contrast, amino(thio)carbonylation reactions of imines with iminoisocyanates and iminoisothiocyanates proved more efficient, providing access to triazolone and triazole-thione cores. The dipole products can be converted to valuable heterocyclic cores through simple derivatization reactions.
各种氮取代的异（硫）氰酸酯参与 [3 + 2]-环加成反应，形成含有三唑酮、三唑硫酮和吡唑硫酮核的亚胺亚胺。首先，异硫氰酸亚胺被证明与张力烯烃发生氨基硫代甲酰化反应，与最近报道的异氰酸酯反应进行比较，突出了它们较低的反应性。相比之下，亚胺与异氰酸酯和异硫氰酸酯的氨基（硫）羰基化反应效率更高，为三唑酮和三唑硫酮核的合成提供了途径。偶极产物可以通过简单的衍生化反应转化为有价值的杂环核。
