AlCl3-Promoted Intramolecular Indolinone-Quinolone Rearrangement of Spiro[indoline-3,2′-quinoxaline]-2,3′-diones: Easy Access to Quinolino[3,4-b]quinoxalin-6-ones,The Journal of Organic Chemistry

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AlCl3-Promoted Intramolecular Indolinone-Quinolone Rearrangement of Spiro[indoline-3,2′-quinoxaline]-2,3′-diones: Easy Access to Quinolino[3,4-b]quinoxalin-6-ones
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-12-27 , DOI: 10.1021/acs.joc.3c01906
Vakhid A Mamedov ₁ , Venera R Galimullina ₁ , Zheng-Wang Qu ₂ , Hui Zhu ₂ , Victor V Syakaev ₁ , Leisan R Shamsutdinova ₁ , Mikhail A Sergeev ₁ , Il'dar Kh Rizvanov ₁ , Aidar T Gubaidullin ₁ , Oleg G Sinyashin ₁ , Stefan Grimme ₂

Affiliation

A facile and direct intramolecular indolinone-quinolone rearrangement was developed for the synthesis of quinolino[3,4-b]quinoxalin-6-ones from spiro[indoline-3,2′-quinoxaline]-2,3′-diones, which are readily available with use of isatines, malononitrile, and 1,2-phenylenediamines under quite mild conditions. This efficient approach provides excellent yields and could potentially be used for the construction of a diverse library of quinolino[3,4-b]quinoxalin-6-ones for high-throughput screening in medicinal chemistry. The reaction mechanism is explored by extensive DFT calculations.

中文翻译：

AlCl3促进的螺[吲哚啉-3,2'-喹喔啉]-2,3'-二酮分子内吲哚酮-喹诺酮重排：轻松获得喹啉[3,4-b]喹喔啉-6-酮

开发了一种简便直接的分子内吲哚酮-喹诺酮重排，用于从螺环[吲哚啉-3,2'-喹喔啉]-2,3'-二酮合成喹啉代[3,4- b ]喹喔啉-6-酮，其为在相当温和的条件下使用靛红、丙二腈和 1,2-苯二胺很容易获得。这种有效的方法提供了优异的产量，并有可能用于构建不同的喹啉并[3,4- b ]喹喔啉-6-酮文库，用于药物化学中的高通量筛选。通过广泛的 DFT 计算探索了反应机理。

更新日期：2023-12-27

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