Rhodium-Catalyzed [2+2+2] Cycloaddition of Oximes and Diynes To Give Pyridines

被引:34
作者
Xu, Fen [1 ]
Wang, Chunxiang [1 ]
Wang, Dongping [1 ]
Li, Xincheng [1 ]
Wan, Boshun [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
基金
中国国家自然科学基金;
关键词
cycloaddition; heterocycles; oximes; pyridines; rhodium; ARYL ETHYNYL ETHERS; ONE-POT SYNTHESIS; SUBSTITUTED PYRIDINES; UNACTIVATED NITRILES; OLEFIN COMPLEXES; ALKYNES; CYCLOTRIMERIZATION; ALPHA; OMEGA-DIYNES; CONSTRUCTION; 2,2'-BIPYRIDINES;
D O I
10.1002/chem.201203909
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Oximes and diynes undergo efficient cycloaddition in the presence of a catalytic amount of a cationic rhodium(I)/dppf complex (see scheme). Spontaneous dehydration of the initially formed cycloadducts leads to the formation of a variety of substituted pyridines in moderate to good yields. The transformation could also be achieved in a one-pot procedure using aldehydes. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2252 / 2255
页数:4
相关论文
共 65 条
[1]   Nickel-Catalyzed, Directing-Group-Assisted [2+2+2] Cycloaddition of Imine and Alkynes [J].
Adak, Laksmikanta ;
Chan, Wei Chuen ;
Yoshikai, Naohiko .
CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (02) :359-362
[2]   Mechanistic Studies into Metal-Catalyzed Aldoxime to Amide Rearrangements [J].
Allen, C. Liana ;
Lawrence, Ruth ;
Emmett, Liam ;
Williams, Jonathan M. J. .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) :3262-3268
[3]  
[Anonymous], ORGANIC CHEM
[4]  
Beckmann E., 1886, Ber, V19, P988
[5]   ORGANOCOBALT COMPOUNDS IN THE SYNTHESIS OF PYRIDINES - AN EXAMPLE OF STRUCTURE-EFFECTIVITY RELATIONSHIPS IN HOMOGENEOUS CATALYSIS [J].
BONNEMANN, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (04) :248-262
[6]  
Bonnemann H., 1985, Angew. Chem., V97, P264
[7]   [2+2+2] cycloaddition reactions catalyzed by transition metal complexes [J].
Chopade, Pramod R. ;
Louie, Janis .
ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (16-17) :2307-2327
[8]   Iron-Catalyzed Cycloaddition of Alkynenitriles and Alkynes [J].
D'Souza, Brendan R. ;
Lane, Timothy K. ;
Louie, Janis .
ORGANIC LETTERS, 2011, 13 (11) :2936-2939
[9]   Recent advances in [2+2+2] cycloaddition reactions [J].
Dominguez, Gema ;
Perez-Castells, Javier .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3430-3444
[10]   Synthesis of Aminopyridines and Aminopyridones by Cobalt-Catalyzed [2+2+2] Cycloadditions Involving Yne-Ynamides: Scope, Limitations, and Mechanistic Insights [J].
Garcia, Pierre ;
Evanno, Yannick ;
George, Pascal ;
Sevrin, Mireille ;
Ricci, Gino ;
Malacria, Max ;
Aubert, Corinne ;
Gandon, Vincent .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (14) :4337-4344