Microwave-Enhanced Rhodium-Catalyzed [2+2+2] Cycloaddition Reactions To Afford Highly Functionalized Pyridines and Bipyridines

被引：29

作者：

Garcia, Lidia ^{[1
]}

Pla-Quintana, Anna ^{[1
]}

Roglans, Anna ^{[1
]}

Parella, Teodor ^{[2
]}

机构：

[1] Univ Girona, Dept Quim, Girona 17071, Spain

[2] Univ Autonoma Barcelona, Serv RMN, E-08193 Barcelona, Spain

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 18期

关键词：

Cycloaddition; Microwave chemistry; Rhodium; Nitrogen heterocycles; Fused-ring systems; NITRILES; COCYCLOTRIMERIZATION; CYCLOTRIMERIZATION; CONSTRUCTION; DERIVATIVES; COMPLEX;

D O I：

10.1002/ejoc.200901318

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rhodium(I)-catalyzed [2+2+2] cycloaddition reactions of N-tosyl-, carbon-, and oxygen-tethered cyanodiynes in a completely intramolecular fashion have been optimized to afford highly functionalized pyridines by conventional and/or microwave heating. Microwaves have been shown to enhance the process by allowing the reaction to be conducted effectively in short reaction times. The methodology has been extended for the synthesis of bipyridines, either by treating a cyanodiyne with an appended pyridine or by conducting a double [2+2+2] cycloaddition reaction on a dicyanotetrayne scaffold. The choice of the solvent in the microwave heating reaction has been shown to be crucial for the success of the process.

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页码：3407 / 3415

页数：9

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