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

被引：3

作者：

Mamedov, Vakhid A. ^{[1
]}

Galimullina, Venera R. ^{[1
]}

Qu, Zheng-Wang ^{[2
]}

Zhu, Hui ^{[2
]}

Syakaev, Victor V. ^{[1
]}

Shamsutdinova, Leisan R. ^{[1
]}

Sergeev, Mikhail A. ^{[1
]}

Rizvanov, Il'dar Kh. ^{[1
]}

Gubaidullin, Aidar T. ^{[1
]}

Sinyashin, Oleg G. ^{[1
]}

Grimme, Stefan ^{[2
]}

机构：

[1] Russian Acad Sci, AE Arbuzov Inst Organ & Phys Chem, RFC Kazan Sci Ctr, Kazan 420088, Russia

[2] Univ Bonn, Mulliken Ctr Theoret Chem, D-53115 Bonn, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 89卷 / 02期

关键词：

QUINOXALINE-BASED INHIBITORS; TRANSITION-STATE; REVERSE-TRANSCRIPTASE; PEROXYFORMIC ACID; DERIVATIVES; EPOXIDATION; POTENT; ALKALOIDS; BINDING; DNA;

D O I：

10.1021/acs.joc.3c01906

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：898 / 917

页数：20

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