Synthesis of Thio and Selenoethers of Cyclic β-Hydroxy Carbonyls and Amino Uracils: A Metal-Free Regioselective I2/DMSO Mediated Reaction

被引：32

作者：

Jana, Asim ^{[1
]}

Panday, Anoop Kumar ^{[1
]}

Mishra, Richa ^{[1
]}

Parvin, Tasneem ^{[2
]}

Choudhury, Lokman H. ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Patna 801103, Bihar, India

[2] Natl Inst Technol Patna, Dept Chem, Patna 800005, Bihar, India

来源：

CHEMISTRYSELECT | 2017年 / 2卷 / 29期

关键词：

Sulfenylation; Selenylation; Amino Uracil; Amino Pyrazole; Iodine Catalysis; Metal-free catalyst; C-H activation; BOND FORMATION; SELENIUM; ARYL; OXIDATION; SULFUR; POTENT; FUNCTIONALIZATION; ORGANOSELENIUM; SULFENYLATION; HETEROCYCLES;

D O I：

10.1002/slct.201702066

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A simple and practical method has been developed using I-2/DMSO for the construction of C-S and C-Se bonds in pharmaceutically important cyclic beta-hydroxy carbonyls such as 4-hydroxy-6-methyl-2H-pyran-2-one, 4-hydroxy-1-methylquinolin-2(1H)-one, quinoline-2,4-diol and heterocyclic enamines such as amino uracil and amino pyrazole derivatives under mild reaction conditions. A series of thio and seleno ethers have been synthesized directly from thiols and selenols in the presence of in situ iodonium ion generated from the I-2/DMSO combination in good to very good yields. This metal-free dehydrogenative C-S and C-Se coupling reaction goes via C(sp(2))-H bond activation and works under conventional as well as microwave heating. Under microwave conditions, reactions complete within 15 minutes with very good yields.

引用

页码：9420 / 9424

页数：5

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