Synthesis of Pyrroles through Rhodium(III)-Catalyzed Reactions of Allylamines and Alkenes

被引:37
作者
Kim, Dong-Su [1 ]
Seo, Yong-Sik [1 ]
Jun, Chul-Ho [1 ]
机构
[1] Yonsei Univ, Dept Chem, Seoul 120749, South Korea
基金
新加坡国家研究基金会;
关键词
C-H ACTIVATION; NATURAL-PRODUCTS; N-ANNULATION; CATALYZED REACTIONS; COUPLING REACTIONS; ORGANIC-SYNTHESIS; BOND FORMATION; ALKYNES; BENZYLAMINES; LAMELLARINS;
D O I
10.1021/acs.orglett.5b01811
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pyrrole derivatives are generated in reactions of allylamines with alkenes that are promoted by a Rh(III) catalyst in the presence of AgOAc. This process, which involves chelation assisted C-H bond activation and N-annulation, is applied to a three step synthesis of Zomepirac.
引用
收藏
页码:3842 / 3845
页数:4
相关论文
共 38 条
[1]  
[Anonymous], 2015, ACCOUNTS CHEM RES, V48, P1, DOI DOI 10.1016/J.WOCN.2014.11.001
[2]   Pyrrole syntheses by multicomponent coupling reactions [J].
Balme, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6238-6241
[3]   Pyrrole: a resourceful small molecule in key medicinal hetero-aromatics [J].
Bhardwaj, Varun ;
Gumber, Divya ;
Abbot, Vikrant ;
Dhiman, Saurabh ;
Sharma, Poonam .
RSC ADVANCES, 2015, 5 (20) :15233-15266
[4]   Iron-catalyzed reactions in organic synthesis [J].
Bolm, C ;
Legros, J ;
Le Paih, J ;
Zani, L .
CHEMICAL REVIEWS, 2004, 104 (12) :6217-6254
[5]   Rhodium-Catalyzed C-C Bond Formation via Heteroatom-Directed C-H Bond Activation [J].
Colby, Denise A. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
CHEMICAL REVIEWS, 2010, 110 (02) :624-655
[6]   Palladium-catalyzed bicyclization processes in the one step construction of heteropolycyclic ring systems [J].
Conreaux, D. ;
Bouyssi, D. ;
Monteiro, N. ;
Balme, G. .
CURRENT ORGANIC CHEMISTRY, 2006, 10 (12) :1325-1340
[7]   Olefin cross-metathesis for the synthesis of heteroaromatic compounds [J].
Donohoe, Timothy J. ;
Bower, John F. ;
Chan, Louis K. M. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (07) :1322-1328
[8]   Recent advances in the synthesis of pyrroles by multicomponent reactions [J].
Estevez, Veronica ;
Villacampa, Mercedes ;
Menendez, J. Carlos .
CHEMICAL SOCIETY REVIEWS, 2014, 43 (13) :4633-4657
[9]   Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis [J].
Evano, Gwilherm ;
Blanchard, Nicolas ;
Toumi, Mathieu .
CHEMICAL REVIEWS, 2008, 108 (08) :3054-3131
[10]   Lamellarins and related pyrrole-derived alkaloids from marine organisms [J].
Fan, Hui ;
Peng, Jiangnan ;
Hamann, Mark T. ;
Hu, Jin-Feng .
CHEMICAL REVIEWS, 2008, 108 (01) :264-287