Consecutive SNH and Suzuki-Miyaura Cross-Coupling Reactions - an Efficient Synthetic Strategy to Pyrimidines Bearing Pyrrole and Indole Fragments

被引：24

作者：

Verbitskiy, Egor V. ^{[1
]}

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

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

Chupakhin, Oleg N. ^{[1
,2
]}

Cheprakova, Ekaterina M. ^{[1
]}

Slepukhin, Pavel A. ^{[1
]}

Pervova, Marina G. ^{[1
]}

Ezhikova, Marina A. ^{[1
]}

Kodess, Mikhail I. ^{[1
]}

机构：

[1] Russian Acad Sci, Ural Branch, I Postovsky Inst Organ Synth, Ekaterinburg 620041, Russia

[2] Ural Fed Univ, BN Yeltsin, Ekaterinburg 620002, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2012年 / 2012卷 / 33期

基金：

俄罗斯基础研究基金会;

关键词：

Synthetic methods; Cross-coupling; Nucleophilic substitution; Nitrogen heterocycles; Microwave chemistry; AROMATIC-SUBSTITUTION REACTIONS; NUCLEOPHILIC-SUBSTITUTION; PROTONATED 1,3-DIAZINES; HYDROGEN; ARYL;

D O I：

10.1002/ejoc.201201035

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The combination of the SuzukiMiyaura cross-coupling and nucleophilic aromatic substitution of hydrogen reactions is a versatile tool for the syntheses of 4-(1R-pyrrol-2-yl)- and 4-(1R-indol-3-yl)-5-(hetero)aryl-substituted pyrimidines from commercially available 5-bromopyrimidine. The SNH [AE, (additionelimination)] and SNH [AO, (additionoxidation)] reactions of 5-bromopyrimidine with pyrroles and indoles were studied by gas chromatographymass spectrometry. The structures of the intermediate sH adducts as well as the pyrrole-(hetero)arylpyrimidine and indole-(hetero)arylpyrimidine dyads were established for the first time by X-ray crystal structure analysis.

引用

页码：6612 / 6621

页数：10

共 27 条

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