Synthesis of Quaternary Spirooxindole 2H‐Azirines under Batch and Continuous Flow Condition and Metal Assisted Umpolung Reactivity for the Ring‐Opening Reaction,Chemistry - An Asian Journal

当前位置： X-MOL 学术 › Chem. Asian J. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Synthesis of Quaternary Spirooxindole 2H‐Azirines under Batch and Continuous Flow Condition and Metal Assisted Umpolung Reactivity for the Ring‐Opening Reaction
Chemistry - An Asian Journal ( IF 3.5 ) Pub Date : 2021-01-19 , DOI: 10.1002/asia.202001418
Girish Singh Bisht ₁ , Tenzin Dolkar Dunchu ₂ , Boopathy Gnanaprakasam ₃

Affiliation

An efficient and new approach for the synthesis of spirooxindole 2H‐azirines via intramolecular oxidative cyclization of 3‐(amino(phenyl)methylene)‐indolin‐2‐one derivatives in the presence of I₂ and Cs₂CO₃ under batch/continuous flow is described. This method is mild and facile to synthesize a variety of spirooxindole 2H‐azirines derivatives in gram‐scale. Furthermore, we have synthesized spiroaziridine derivatives from spirooxindole 2H‐azirines derivatives via addition of Grignard reagent. In addition, we discloses an metal assisted attack of Grignard nucleophile at N‐centre rather than C‐ of the spirooxindole 2H‐azirines, which concurrently underwent ring opening of transient aziridines to afford N‐substituted Z‐3‐(aminophenyl)indolin‐2‐one. A plausible mechanism for azirination and ring‐opening reaction is also presented.

中文翻译：

间歇和连续流动条件下季螺氧杂吲哚2H-嗪的合成及开环反应的金属辅助Uppolung反应性

在I ₂和Cs ₂ CO _3存在下以分批/连续流动的方式通过3-（氨基（苯基）亚甲基）-吲哚啉-2-酮衍生物的分子内氧化环化反应合成螺环吲哚2H嗪的有效方法描述。该方法温和且易于以克级合成各种螺氧基吲哚2H-叠氮基衍生物。此外，我们还通过添加格氏试剂从螺并吲哚2H- azirines衍生物合成了螺并氮丙啶衍生物。此外，我们公开了格氏亲核试剂在N处的金属辅助攻击螺环吲哚2H-叠氮基的中心位置而不是C-位置，同时进行瞬态氮丙啶的开环反应，得到N-取代的Z- 3-（氨基苯基）吲哚-2-基。还提出了一种可行的叠氮化和开环反应的机理。

更新日期：2021-03-15

点击分享查看原文

点击收藏

阅读更多本刊新发论文