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首页> 外文期刊>European journal of organic chemistry >Exocyclic-Endocyclic N-Acyliminium Ion Equilibration via an Intramolecular alpha-Thioamidoalkylation in the Synthesis of Fused N,S-Heterocyclic Systems:Some New Parameters
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Exocyclic-Endocyclic N-Acyliminium Ion Equilibration via an Intramolecular alpha-Thioamidoalkylation in the Synthesis of Fused N,S-Heterocyclic Systems:Some New Parameters

机译：稠合的N，S-杂环体系合成中通过分子内α-硫酰胺基烷基化作用的环外-环内N-酰基亚胺离子平衡：一些新参数

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摘要

The reactivity of N-[aryl(or alkyl)thio(oxo or seleno)alkylami-dals 6 bearing the N-(CH_2)_n-X-(CH_2)_m-Ar functionality towards neat TFA has been examined.Substrates of type 6 give,together with the products 11,17,19,and 25 of the "expected" pi-cyclization process,the "unexpected" products 12,18,and 26 resulting from a new tandem heteroamidoalk-ylation/isomerization/pi-cyclization.The composition of the final isomeric mixture depends on the temperature of the reaction,with a high selectivity in favor of the "expected" pi-cyclization product 11 as a thermodynamic isomer.Furthermore,the results demonstrate again the relevance of TFA catalysis and support two reaction pathways involving the for-mation of an aza-sulfonium cation A as a valuable intermediate which undergoes the pi-cyclization process alone or in tandem with the thiocyclization/isomerization to give the cy-clized products cited above.For the latter tandem reaction,we have established clearly that the n value should be equal to 1,the process can be performed independently for both the succinimide and phthalimide series,the reaction depends on the nucleophilicity of the heteroatom,and can be generalized to other heterocycles.Only the role of the benzene substitution has still to be totally elucidated.
机译：研究了带有N-（CH_2）_n-X-（CH_2）_m-Ar官能团的N- [芳基（或烷基）硫代（氧代或硒代）烷基酰胺基6对纯净TFA的反应性。类型6的底物与“预期的” pi环化过程的产物11、17、19和25一起，给出了由新的串联杂酰胺基烷基化/异构化/ pi环化产生的“意外的”产物12、18和26。最终异构体混合物的组成取决于反应的温度，具有高选择性，有利于“预期的”π-环化产物11作为热力学异构体。此外，结果再次证明了TFA催化的相关性并支持两种形成氮杂-阳离子A作为有价值的中间体的反应途径，可单独或与硫环化/异构化一起进行pi环化过程以生成上述环化产物。我们已经清楚地确定n值应该相等在图1中，该过程可以针对琥珀酰亚胺和邻苯二甲酰亚胺系列独立地进行，该反应取决于杂原子的亲核性，并且可以推广至其他杂环。仅苯取代的作用尚待完全阐​​明。

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