I2-Cs2CO3 Mediated Intramolecular C2-Amination and Oxidative Rearrangement Cascade of C-3 Phenylthio Indoles: A Route to Synthesize Thiosulfonate-Embedded 2-Iminoindolin-3-ones

被引：3
|
作者：
Singh, Gargi [1 ]
Marupalli, Sasi Sree [1 ]
Arockiaraj, Mariyaraj [1 ]
Rajeshkumar, Venkatachalam [1 ]
机构：
[1] Natl Inst Technol Warangal, Dept Chem, Organ Synth & Catalysis Lab, Hanumakonda 506004, Telangana, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 08期
关键词：
ONE-POT SYNTHESIS; TRYPTANTHRIN DERIVATIVES; CONSTRUCTION; IODINE; PYRROLOINDOLINES; CYCLIZATION; DISULFIDES; INHIBITORS; ACCESS; CS2CO3;
D O I：
10.1021/acs.joc.4c00056
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient, transition-metal-free protocol employing I-2/Cs2CO3 for the synthesis of thiosulfonate containing 2-iminoindolin-3-ones motifs has been developed from C-3 phenylthio indoles. The reaction proceeded through intramolecular cyclization involving C-N bond formation, leading to the formation of indole-fused benzothiazines as a key intermediate. Remarkably, Cs2CO3 played a crucial role in the reaction as an oxygen source, enabling oxidative rearrangement with [1,4]-sulfonyl migration to furnish the final products with the formation of multiple functional groups such as C & boxH;O, C & boxH;N, and S-SO2.
引用
收藏
页码：5861 / 5870
页数：10
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