"Urea to Urea" Approach: Access to Unsymmetrical Ureas Bearing Pyridyl Substituents

被引：12

作者：

Kasatkina, Svetlana O. ^{[1
]}

Geyl, Kirill K. ^{[1
]}

Baykov, Sergey V. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

Boyarskiy, Vadim P. ^{[1
]}

机构：

[1] St Petersburg State Univ, Inst Chem, Univ Skaya 7-9, St Petersburg 199034, Russia

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2022年 / 364卷 / 07期

基金：

俄罗斯科学基金会;

关键词：

N-hetaryl ureas; Metal-free synthesis; Masked hetaryl isocyanates; Amines; Heterocycles; MASKED ISOCYANATES FACILE; CATALYZED CARBONYLATION; GLUCOKINASE ACTIVATORS; BLOCKED ISOCYANATES; BIOLOGICAL EVALUATION; PARALLEL SYNTHESIS; ANION-BINDING; DISCOVERY; DERIVATIVES; AMINES;

D O I：

10.1002/adsc.202101490

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A protocol for the synthesis of unsymmetrical ureas substituted by pyridyl/quinolinyl moiety has been developed. This method concluded in metal- and base-free reamination of N,N-dimethyl-N'-hetaryl ureas with a wide range of aryl and alkyl amines. The isolated yields vary from 40 to 96% depending on the nucleophilicity of the amines. The scope of this method includes more than 50 examples. The reaction is not hindered by either donor or acceptor groups as well as diverse functionalities. The synthesis can be easily scaled to gram quantities. Theoretical calculations supported by experimental data allowed us to propose a plausible mechanism for the process. This reaction takes place through the intermediate formation of hetaryl isocyanate.

引用

页码：1295 / 1304

页数：10

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