Regioselective Syntheses of Substituted Pyridines and 2,2′-Bipyridines by Cobalt-Catalyzed [2+2+2] Cycloaddition of α,ω-Diynes with Nitriles

被引：36

作者：

Sugiyama, Yu-ki ^{[1
]}

Okamoto, Sentaro ^{[1
]}

机构：

[1] Kanagawa Univ, Dept Mat & Life Chem, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan

来源：

SYNTHESIS-STUTTGART | 2011年 / 14期

关键词：

cycloadditions; heterocycles; homogeneous catalysis; pyridines; regioselectivity; 2 DIFFERENT ALKYNES; ONE-STEP SYNTHESIS; INTRAMOLECULAR CYCLOTRIMERIZATION; CONSTRUCTION; ACETYLENES; LIGANDS; TRIYNES; ROUTE;

D O I：

10.1055/s-0030-1260068

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of a 1,2-bis(diphenylphosphino) ethanecobalt(II) chloride-zinc catalyst in 1-methylpyrrolidin-2-one at room temperature to 50 degrees C, alpha,omega-diynes reacted with nitriles by a [2+2+2] cycloaddition pathway to give annulated pyridines or 2,2'-bipyridines. The regioselectivity of the reaction is controlled by a combination of steric and electronic effects. The reaction of diynes with a terminal trimethylsilyl group gave the corresponding 3-(trimethylsilyl) pyridines exclusively; these products could be proto-or halodesilylated to give the corresponding protonated or halogenated pyridines or 2,2'-bipyridines.

引用

页码：2247 / 2254

页数：8

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