PALLADIUM-CATALYZED INTRAMOLECULAR ADDITION OF AMINES TO ACETYLENES - SYNTHESIS OF CYCLIC IMINES

被引：70

作者：

FUKUDA, Y ^{[1
]}

MATSUBARA, S ^{[1
]}

UTIMOTO, K ^{[1
]}

机构：

[1] KYOTO UNIV,FAC ENGN,DEPT IND CHEM,KYOTO 606,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 20期

关键词：

D O I：

10.1021/jo00020a023

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular aminopalladation of alkynylamines gave intermediary alkenylpalladium compounds that hydrolyzed and isomerized to thermodynamically stable cyclic imines. Treatment of 3-alkynylamines with a catalytic amount of PdCl2(MeCN)2 gave exclusively 1-pyrrolines in good yields; 5-alkynylamines afforded 2,3,4,5-tetrahydropyridines selectively. Treatment of 4-alkynylamines with Pd(II) afforded mixtures of both 5- and 6-membered cyclic imines. Applications to the synthesis of some naturally occurring alkaloids are also described.

引用

页码：5812 / 5816

页数：5

共 39 条

[1]

[Anonymous], 1981, SYNTHESIS ACETYLENES

[2]

ASTIER A, 1978, TETRAHEDRON LETT, P2051

[3] CHEMICALS FROM THE GLANDS OF ANTS [J].