Copper-Catalyzed Aerobic Oxidative Cyclization of Hydrazones to Pyrazolidinones

被引：4
作者：
Dos Santos, Aurelie [1 ]
El Kaim, Laurent [1 ]
Grimaud, Laurence [1 ]
Ronsseray, Caroline [1 ]
机构：
[1] Ecole Natl Super Tech Avancees, Lab Chim & Proc, DCSO UMR CNRS ENSTA Ecole Polytech 7652, F-75739 Paris 15, France
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 2011卷 / 17期
关键词：
Hydrazones; Cycloaddition; Oxidation; Copper; Multicomponent reactions; INTRAMOLECULAR 1,3-DIPOLAR CYCLOADDITION; MULTICOMPONENT REACTIONS; CASCADE REACTIONS; DERIVATIVES; ACID; CHEMISTRY; ALDEHYDES; ALCOHOLS; SYSTEMS;
D O I：
10.1002/ejoc.201100261
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
N-Aryl hydrazones participate, under copper catalysis, in a [3+2] cycloaddition/aerobic oxidation cascade reaction to form pyrazolidinones. The starting hydrazones were prepared by three-component coupling of allylic amines, acyl chlorides, and aryl diazonium salts.
引用
收藏
页码：3117 / 3121
页数：5
相关论文
共 53 条
[1]   New versatile approach to α-hydrazonoesters and amino acid derivatives through a modified Japp-Klingemann reaction [J].
Atlan, V ;
El Kaim, L ;
Supiot, C .
CHEMICAL COMMUNICATIONS, 2000, (15) :1385-1386
[2]   The use of hydrazones for efficient mannich type coupling with aldehydes and secondary amines [J].
Atlan, V ;
Bienaymé, H ;
El Kaim, L ;
Majee, A .
CHEMICAL COMMUNICATIONS, 2000, (17) :1585-1586
[3]  
BADAWY MA, 1988, HETEROCYCLES, V27, P7
[4]   An Oxidative Prins-Pinacol Tandem Process and its Application to the synthesis of (-)-Platensimycin [J].
Beaulieu, Marc-Andre ;
Sabot, Cyrille ;
Achache, Nabil ;
Guerard, Kimiaka C. ;
Canesi, Sylvain .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (37) :11224-11228
[5]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[6]  
2-A
[7]   Rapid complexity generation in natural product total synthesis [J].
Davies, Huw M. L. ;
Sorensen, Erik J. .
CHEMICAL SOCIETY REVIEWS, 2009, 38 (11) :2981-2982
[8]   Multicomponent Domino Cyclization-Oxidative Aromatization on a Bifunctional Pd/C/K-10 Catalyst: An Environmentally Benign Approach toward the Synthesis of Pyridines [J].
de Paolis, Omar ;
Baffoe, Jonathan ;
Landge, Shainaz M. ;
Toeroek, Bela .
SYNTHESIS-STUTTGART, 2008, (21) :3423-3428
[9]   Recent developments in isocyanide based multicomponent reactions in applied chemistry [J].
Dömling, A .
CHEMICAL REVIEWS, 2006, 106 (01) :17-89
[10]   Recent advances in isocyanide-based multicomponent chemistry [J].
Dömling, A .
CURRENT OPINION IN CHEMICAL BIOLOGY, 2002, 6 (03) :306-313
123456