Palladium-Catalyzed Coupling of 3-Halo-Substituted Coumarins, Chromenes, and Quinolones with Various Nitrogen-Containing Nucleophiles

被引：32

作者：

Soussi, Mohamed Ali ^{[1
]}

Audisio, Davide ^{[1
]}

Messaoudi, Samir ^{[1
]}

Provot, Olivier ^{[1
]}

Brion, Jean-Daniel ^{[1
]}

Alami, Mouad ^{[1
]}

机构：

[1] Univ Paris 11, CNRS, BioCIS UMR 8076, Chim Therapeut Lab,Fac Pharm, F-92296 Chatenay Malabry, France

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 26期

关键词：

Palladium; Heterocycles; C-N coupling; Amination; EFFICIENT ROUTE; NOVOBIOCIN; INHIBITORS; ANALOGS; TOSYLHYDRAZONES; DERIVATIVES; ARYLATION; BENZILS; ACCESS;

D O I：

10.1002/ejoc.201100480

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and general palladium-catalyzed coupling reaction between 3-bromocoumarins, 3-broinoquinolin-2(1H)-ones, and 3-iodo-2H-chromenes with a variety of nitrogen-containing nucleophiles (azole, amide, lactam, sulfonamide, aniline, amine, and urea) is described. The reaction proceeded rapidly and cleanly in dioxane providing the coupling products in good to excellent yields. The chemoselectivity of this reaction was also studied with polyhalocoumarins. Under optimized conditions, these underwent a site-selective amination at the C-3-Br bond, regardless of the nature of the nitrogen-containing nucleophile used.

引用

页码：5077 / 5088

页数：12

共 64 条

[1]

ALAMI M, 2008, Patent No. 122620

[2] A convenient and expeditious synthesis of 3-(N-substituted) aminocoumarins via palladium-catalyzed Buchwald-Hartwig coupling reaction [J].