Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring

Eszter Kókai; Gyula Simig; Balázs Volk

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Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring

机译：关于N-未保护的3-单取代的羟吲哚的3-烷基化的文献综述和进一步的研究。 N-未保护的3,3-二取代的吲哚的实际合成及其在芳环上的后续转化

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The paper provides a comprehensive review of the base-catalysed C3-alkylation of N-unprotected-3-monosubstituted oxindoles. Based on a few, non-systematic studies described in the literature using butyllithium as the deprotonating agent, an optimized method has now been elaborated, via the corresponding lithium salt, for the selective C3-alkylation of this family of compounds. The optimal excess of butyllithium and alkylating agent, and the role of the halogen atom in the latter (alkyl bromides vs. iodides) were also studied. The alkylation protocol has also been extended to some derivatives substituted at the aromatic ring. Finally, various substituents were introduced into the aromatic ring of the N-unprotected 3,3-dialkyloxindoles obtained by this optimized method. View Full-Text

机译：本文对N-未保护的3-单取代的羟吲哚的碱催化的C3-烷基化进行了全面综述。基于文献中描述的使用丁基锂作为去质子化剂的一些非系统性研究，现在已经通过相应的锂盐为该化合物家族的选择性C3-烷基化开发了一种优化方法。还研究了丁基锂和烷基化剂的最佳过量量，以及卤素原子在后者中的作用（烷基溴与碘化物）。烷基化方案也已扩展到在芳环上取代的一些衍生物。最后，将各种取代基引入通过这种优化方法获得的N-未保护的3，3-二烷基氧吲哚的芳环中。查看全文

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《Molecules》 |2017年第1期|共18页
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Eszter Kókai; Gyula Simig; Balázs Volk;
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中图分类有机化学;
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1. Highly regioselective synthesis of 3-alkenyl-oxindole ring-fused 3,3'-disubstituted oxindoles via direct gamma-substitution of Morita-Baylis-Hillman carbonates of isatins with 3-substituted oxindoles [J] . Ting-Ting Feng, Xuan Huang, Xiong-Li Liu, Organic & biomolecular chemistry . 2014,第46期

机译：通过森田的Morita-Baylis-Hillman碳酸盐直接用3个取代的羟吲哚取代γ的高γ选择性合成3-烯基-羟吲哚环稠合的3,3'-二取代的羟吲哚
2. Synthesis of 3,3-disubstituted oxindoles from anilines nitrosated in situ: a radical-promoted reaction of aromatic amines with N-arylacrylamides [J] . Ni Zhangqin, Wang Sichang, Huang Xin, Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2015,第19期

机译：由原位亚硝化的苯胺合成3,3-二取代的羟吲哚：芳香胺与N-芳基丙烯酰胺的自由基促进反应
3. Synthesis of 3,3-disubstituted oxindoles by palladium-catalyzed asymmetric intramolecular α-arylation of amides: Reaction development and mechanistic studies [J] . Katayev D., Jia Y.-X., Sharma A.K., Chemistry: A European journal . 2013,第36期

机译：钯催化酰胺的不对称分子内α-芳基化反应合成3,3-二取代的羟吲哚：反应发展及机理研究
4. Studies toward the synthesis of EFGH ring system of diazonamide A: Pummerer chemistry applied toward the synthesis of 3,3-spirocyclic oxindoles. [D] . Vidulova, Daniela Boneva. 2005

机译：对重氮酰胺A的EFGH环系统合成的研究：Pummerer化学方法用于3,3-螺环氧吲哚的合成。
5. Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 33-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring [O] . Eszter Kókai, Gyula Simig, Balázs Volk 2017

机译：关于N-未保护的3-单取代的羟吲哚的3-烷基化的文献综述和进一步的研究。 N-未保护的33-二取代的吲哚的实际合成及其在芳环上的后续转化
6. Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring [O] . Eszter Kókai, Gyula Simig, Balázs Volk 2016

机译：关于N-未保护的3-单取代氧吲哚3-烷基化的文献综述和进一步研究。 N-未保护的3,3-二取代氧吲哚的实际合成及其在芳环上的后续转化

Literature Survey and Further Studies on the 3-Alkylation of N-Unprotected 3-Monosubstituted Oxindoles. Practical Synthesis of N-Unprotected 3,3-Disubstituted Oxindoles and Subsequent Transformations on the Aromatic Ring

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