Microwave-Assisted Regioselective Friedel-Crafts Arylation by BF3 . OEt2: A Facile Synthetic Access to 3-Substituted-3-Propargyl Oxindole Scaffolds

被引：11
|
作者：
Laxmikeshav, Kritika [1 ]
Sakla, Akash P. [1 ]
Rasane, Sai [1 ]
John, Stephy Elza [1 ]
Shankaraiah, Nagula [1 ]
机构：
[1] Natl Inst Pharmaceut Educ & Res NIPER, Dept Med Chem, Hyderabad 500037, Telangana, India
来源：
CHEMISTRYSELECT | 2020年 / 5卷 / 23期
关键词：
C-C bond formation; 3; 3-disubstituted oxindole; Friedel-Crafts arylation; Lewis acids; Microwave Chemistry; AROMATIC-COMPOUNDS; ORGANIC-SYNTHESIS; TERMINAL ALKYNES; ALLYLIC ALCOHOLS; GREEN SYNTHESIS; ANTI-HIV; PROPARGYLATION; SUBSTITUTION; DESIGN; CYCLOADDITION;
D O I：
10.1002/slct.202001660
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A facile microwave-assisted synthetic strategy for the construction of C-C bondviaregioselective Friedel-Crafts arylation of 3-hydroxy-3-phenylethynyl oxindoles with different electron-rich nucleophiles such as phenols, sulphonamides, anisole, benzofuran, and benzothiophene has been established by employing BF3 . OEt(2)as catalyst. The current protocol attributes mild conditions, cost-effective, transition-metal free synthesis, wide substrate scope and moderate to good yields. Moreover, this method is amenable for the generation of a library of densely substituted 3-(4-hydroxyphenyl)-3-(phenylethynyl) oxindoles and 3-(4-benzenesulphonamide)-3-(phenylethynyl) oxindoles as privileged scaffolds.
引用
收藏
页码：7004 / 7012
页数：9
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