4-methylpyrimidinium ylides. Part 7: 3+2 Dipolar cycloadditions to non-symmetrical substituted alkenes and alkynes

被引：33

作者：

Mangalagiu, II ^{[1
]}

Mangalagiu, GC ^{[1
]}

Deleanu, C ^{[1
]}

Drochioiu, G ^{[1
]}

Petrovanu, MG ^{[1
]}

机构：

[1] Alexandru Ioan Cuza Univ, Dept Organ Chem, Iasi 6600, Romania

来源：

TETRAHEDRON | 2003年 / 59卷 / 01期

关键词：

pyrimidinium ylides; regioselectivity; azabicyclic compounds;

D O I：

10.1016/S0040-4020(02)01453-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The ability of 4-methylpyrimidinium ylides (as 1,3-dipoles) to react with activated non-symmetrical substituted dipolarophiles (alkenes and alkynes) is presented. 4-Methylpyrimidinium ylides did not react with alkenes. With alkynes the reactions are regiospecific, a single regioisomer being obtained. A possible mechanism for the reaction pathway is proposed. For the first time in the pyrimidinium ylides series both isomers resulting from bonding to the 2-and 6-positions of the heterocycle ring were obtained. The appropriate conditions in order to increase the selectivity of one of the isomers were determined. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：111 / 114

页数：4

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