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
吲哚
分子内力
喹喔啉
化学
喹诺酮类
立体化学
药物化学
有机化学
生物化学
抗生素
作者
В. А. Мамедов,Venera R. Galimullina,Zheng‐Wang Qu,Hui Zhu,Victor V. Syakaev,Leisan R. Shamsutdinova,Мikhail A. Sergeev,И. Х. Ризванов,А.Т. Губайдуллин,Оleg G. Sinyashin,Stefan Grimme
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.