Unexpected regio- and chemoselectivity of cationic gold-catalyzed cycloisomerizations of propargylureas: access to tetrasubstituted 3,4-dihydropyrimidin-2(1H)-ones

被引：27

作者：

Pereshivko, Olga P. ^{[1
]}

Peshkov, Vsevolod A. ^{[1
]}

Peshkov, Anatoly A. ^{[1
]}

Jacobs, Jeroen ^{[2
]}

Van Meervelt, Luc ^{[2
]}

Van der Eycken, Erik V. ^{[1
]}

机构：

[1] Univ Leuven KU Leuven, Dept Chem, LOMAC, B-3001 Louvain, Belgium

[2] Univ Leuven KU Leuven, Dept Chem, B-3001 Louvain, Belgium

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 11期

关键词：

ONE-POT; ALKYNES; AMINES; DIHYDROPYRIMIDONES; ALDEHYDES; ADDITIONS;

D O I：

10.1039/c3ob42221f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Cationic gold-catalyzed cycloisomerizations of propargylureas, derived in situ from secondary propargylamines and aryl or alkyl isocyanates, have been studied. The reaction outcome was found to be different from what was previously observed for the tosyl isocyanate-derived ureas in terms of both regio- and chemoselectivity. As a result, the current protocol offers efficient access to the 3,4-dihydropyrimidin-2(1H)-one core through the 6-endo-dig N-cyclization.

引用

页码：1741 / 1750

页数：10

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