One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement

被引：11

作者：

Wang, Chien-Hong ^{[1
]}

Hsieh, Tsung-Han ^{[1
]}

Lin, Chia-Chi ^{[1
]}

Yeh, Wen-Hsiung ^{[1
]}

Lin, Chih-An ^{[1
]}

Chien, Tun-Cheng ^{[1
]}

机构：

[1] Natl Taiwan Normal Univ, Dept Chem, Taipei 11677, Taiwan

来源：

SYNLETT | 2015年 / 26卷 / 13期

关键词：

urea; cyanamide; amidoxime; hydrolysis; Tiemann rearrangement; PALLADIUM-CATALYZED ARYLATION; LIGAND-FREE CONDITIONS; SUBSTITUTED UREAS; PYRIMIDINE NUCLEOSIDES; PHARMACOPHORE MODEL; ROOM-TEMPERATURE; ARYL HALIDES; DERIVATIVES; AMIDOXIMES; INHIBITORS;

D O I：

10.1055/s-0034-1381007

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Amidoximes, obtained from the reaction of nitriles with hydroxylamine, underwent Tiemann rearrangement in the presence of benzenesulfonyl chlorides (TsCl or o-NsCl) to form the N-substituted cyanamides. Subsequently, acidic hydrolysis of the cyanamides afforded the corresponding N-monosubstituted ureas. The synthesis of N-monosubstituted ureas from nitriles was accomplished by three steps in one pot, which provides a direct access to versatile N-monosubstituted urea derivatives from a wide variety of nitriles.

引用

页码：1823 / 1826

页数：4

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