Synthesis of 5-(het)aryl- and 4,5-di(het)ary1-2-(thio)morpholinopyrimidines from 2-chloropyrimidine via SNH and cross-coupling reactions

被引：9

作者：

Cheprakova, E. M. ^{[1
]}

Verbitskiy, E. V. ^{[1
,2
]}

Ezhikova, M. A. ^{[1
]}

Kodess, M. I. ^{[1
]}

Pervova, M. G. ^{[1
]}

Slepukhin, P. A. ^{[1
]}

Toporova, M. S. ^{[1
]}

Kravchenko, M. A. ^{[3
]}

Medvinskiy, I. D. ^{[3
]}

Rusinov, G. L. ^{[1
,2
]}

Charushin, V. N. ^{[1
,2
]}

机构：

[1] Russian Acad Sci, Ural Branch, I Ya Postovsky Inst Organ Synth, Ekaterinburg 620990, Russia

[2] Ural Fed Univ, Ekaterinburg 620002, Russia

[3] Ural Res Inst Phthisiopulmonol, Ekaterinburg 620039, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2014年 / 63卷 / 06期

基金：

俄罗斯基础研究基金会;

关键词：

pyrimidines; morpholine; thiomorpholine; cross-coupling; microwave irradiation; nucleophilic aromatic substitution of hydrogen; antituberculosis activity;

D O I：

10.1007/s11172-014-0602-y

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

It has been shown that various combinations of nucleophilic aromatic substitution of hydrogen (S-N(H)), S-N(ipso) and the microwave-assisted Suzuki cross-coupling reactions are a versatile method for the synthesis of 5-(het)ary1-2-(thio)morpholinopyrimidine and 4,5-di(het)ary1-2(thio)morpholinopyrimidine derivatives. All synthesized pyrimidines were found to be active in micromolar concentrations in vitro against Mycobacterium tuberculosis H(37)Rv.

引用

页码：1350 / 1358

页数：9

共 11 条

[11] Combination of the Suzuki-Miyaura cross-coupling and nucleophilic aromatic substitution of hydrogen (SNH) reactions as a versatile route to pyrimidines bearing thiophene fragments [J].

Verbitskiy, Egor V. ;

Cheprakova, Ekaterina M. ;

Slepukhin, Pavel A. ;

Kodess, Mikhail I. ;

Ezhikova, Marina A. ;

Pervova, Marina G. ;

Rusinov, Gennady L. ;

Chupakhin, Oleg N. ;

Charushin, Valery N. .

TETRAHEDRON, 2012, 68 (27-28) :5445-5452

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