ZIRCONIUM-MEDIATED REACTIONS OF ALKYLPYRAZINES AND ALKYNES - SYNTHESIS OF HIGHLY SUBSTITUTED ALKYLPYRAZINES

被引：30

作者：

GURAM, AS ^{[1
]}

JORDAN, RF ^{[1
]}

机构：

[1] UNIV IOWA, DEPT CHEM, IOWA CITY, IA 52242 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1992年 / 57卷 / 22期

关键词：

D O I：

10.1021/jo00048a038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Sequential one-pot addition of alkylpyrazines, alkynes, and a proton source to a solution of Cp2Zr(Me)(THF)+ (1) in CH2Cl2 at room temperature affords (E)-alkenyl-substituted alkylpyrazines 2-10 in excellent yields. The regio- and stereoselectively observed in these reactions is similar to those observed previously for related early transition metal-mediated reactions and is ascribed to steric and Si electronic effects. Conventional synthetic organic manipulation of the alkenylpyrazines provides easy access to a variety of highly substituted alkylpyrazines including tri- and tetrasubstituted alkylpyrazines 13, 17-20, dibromoalkylpyrazine 14, bromoalkylpyrazine 15, and epoxyalkylpyrazine 16.

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页码：5994 / 5999

页数：6

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