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首页> 外文期刊>Tetrahedron >N-Heterocyclic carbenes from ylides of indolyl-imidazolium, azaindolyl-imidazolium, and indolyl-triazolium salts, and their borane adducts
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N-Heterocyclic carbenes from ylides of indolyl-imidazolium, azaindolyl-imidazolium, and indolyl-triazolium salts, and their borane adducts

机译：吲哚基-咪唑鎓盐，氮杂吲哚基-咪唑鎓盐和吲哚基-三唑鎓盐的烷基化物中的N-杂环卡宾及其硼烷加合物

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摘要

Indol-2-yl-imidazolium salts were deprotonated at N1 of the indole ring to give ylides. Their tautomeric N-heterocyclic carbenes (NHCs) were trapped by sulfur to give imidazole-2-thiones. Treatment of the ylides with triethylborane resulted in the formation of zwitterionic borane adducts. An analogous sequence of reactions was performed with 8-azaindol-2-yl-imidazolium salts, which served as precursor to prepare first representatives of a new heterocyclic ring system on reaction of their NHC-tautomers with triethylborane. Similarly, an indol-2-yl-1,2,4-triazolium salt was examined with respect to ylideeNHC tautomerism and trapping reactions. A nucleophilic ring transformation of indol-3-amine with a 1,3,4- oxadiazolium salt gave an indol-3-yl-triazolium salt, which was converted into a triazolethione by trapping of the tautomeric N-heterocyclic carbene of its ylide.
机译：在吲哚环的N1处使吲哚-2-基-咪唑鎓盐去质子化，得到酰化物。他们的互变异构N-杂环卡宾（NHCs）被硫捕获，得到咪唑-2-硫酮。用三乙基硼烷处理酰基化物导致两性离子硼烷加合物的形成。用8-氮杂吲哚-2-基-咪唑鎓盐进行类似的反应序列，其用作前体以在其NHC-互变异构体与三乙基硼烷反应上制备新的杂环体系的第一代表。类似地，检查了吲哚-2-基-1,2,4-三唑鎓盐的叶立德NHC互变异构和捕获反应。吲哚-3-胺与1,3,4-恶二唑盐的亲核环转化得到吲哚-3-基三唑鎓盐，其通过捕获其叶立德的互变异构N-杂环卡宾而转化为三唑硫酮。

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