Synthesis of Dihydropyrrole Derivatives by a Palladium-Catalyzed Heck and Suzuki Cross-Coupling Cascade Reaction

被引:17
作者
Peng, Jinsong [1 ,2 ]
Zhao, Yan [1 ]
Zhou, Jingjie [1 ]
Ding, Yuehang [1 ]
Chen, Chunxia [1 ]
机构
[1] Northeast Forestry Univ, Dept Chem & Chem Engn, Coll Sci, Harbin 150040, Peoples R China
[2] Northeast Forestry Univ, Postdoctoral Mobile Res Stn Forestry Engn, Harbin 150040, Peoples R China
来源
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 15期
基金
中国国家自然科学基金; 中国博士后科学基金;
关键词
pyrroles; palladium; catalysis; tandem reactions; Heck reaction; Suzuki reaction; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC-ADDITION; STEREOSELECTIVE-SYNTHESIS; CYCLIZATION REACTION; FACILE PREPARATION; DOMINO REACTIONS; ORGANIC HALIDES; 2,3-DIHYDROPYRROLES; AZIRIDINES; BROMOALKYNES;
D O I
10.1055/s-0033-1341265
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An expedient protocol for the synthesis of 5-aryl-2,3-dihydropyrroles, starting from N-tosyl-protected 2-methylprop-2-en-1-amine, alkynyl bromides, and arylboronic acids, is described. The sequential reaction sequence involves nucleophilic addition of the sulfonamide to the alkynyl bromide, followed by a palladium-catalyzed tandem intramolecular Heck and intermolecular Suzuki cross-coupling reaction of the bromoalkene adduct.
引用
收藏
页码:2051 / 2056
页数:6
相关论文
共 45 条
  • [1] Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions
    Bellina, Fabio
    Rossi, Renzo
    [J]. TETRAHEDRON, 2006, 62 (31) : 7213 - 7256
  • [2] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds
    Billingsley, Kelvin L.
    Anderson, Kevin W.
    Buchwald, Stephen L.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (21) : 3484 - 3488
  • [3] Annulations of Enantioenriched Allenylsilanes with in Situ Generated Iminium Ions: Stereoselective Synthesis of Diverse Heterocycles
    Brawn, Ryan A.
    Panek, James S.
    [J]. ORGANIC LETTERS, 2009, 11 (02) : 473 - 476
  • [4] Small-molecule inhibitors of protein geranylgeranyltransferase type I
    Castellano, Sabrina
    Fiji, Hannah D. G.
    Kinderman, Sape S.
    Watanabe, Masaru
    de Leon, Pablo
    Tamanoi, Fuyuhiko
    Kwon, Ohyun
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) : 5843 - +
  • [5] Synthesis of 2,5-Disubstituted 3-Iodofurans via Palladium-Catalyzed Coupling and Iodocyclization of Terminal Alkynes
    Chen, Zhengwang
    Huang, Gao
    Jiang, Huanfeng
    Huang, Huawen
    Pan, Xiaoyan
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (04) : 1134 - 1139
  • [6] Palladium-Catalyzed Three-Component Tandem Cyclization Reaction of 2-(2,3-Allenyl)acylacetates, Organic Halides, and Amines: An Effective Protocol for the Synthesis of 4,5-Dihydro-1H-pyrrole Derivatives
    Cheng, Jiajia
    Jiang, Xuefeng
    Zhu, Can
    Ma, Shengming
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (10) : 1676 - 1682
  • [7] Kinesin spindle protein (KSP) inhibitors.: 9.: Discovery of (2S)-4-(2,5-difluorophenyl)-N-[(3R,4S)-3-fluoro-1-methylpiperidin-4-yl]-2-(hydroxymethyl)-N-methyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxamide (MK-0731) for the treatment of taxane-refractory cancer
    Cox, Christopher D.
    Coleman, Paul J.
    Breslin, Michael J.
    Whitman, David B.
    Garbaccio, Robert M.
    Fraley, Mark E.
    Buser, Carolyn A.
    Walsh, Eileen S.
    Hamilton, Kelly
    Schaber, Michael D.
    Lobell, Robert B.
    Tao, Weikang
    Davide, Joseph P.
    Diehl, Ronald E.
    Abrams, Marc T.
    South, Vicki J.
    Huber, Hans E.
    Torrent, Maricel
    Prueksaritanont, Thomayant
    Li, Chunze
    Slaughter, Donald E.
    Mahan, Elizabeth
    Fernandez-Metzler, Carmen
    Yan, Youwei
    Kuo, Lawrence C.
    Kohl, Nancy E.
    Hartman, George D.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (14) : 4239 - 4252
  • [8] A convenient and efficient ring-opening reaction of aziridines with acetylenes and synthesis of dihydropyrroles
    Ding, CH
    Dai, LX
    Hou, XL
    [J]. TETRAHEDRON, 2005, 61 (40) : 9586 - 9593
  • [9] Facile construction of highly functionalized 2-pyrrolines via FeCl3-catalyzed reaction of aziridines with arylalkynes
    Fan, Jinmin
    Gao, Linfeng
    Wang, Zhiyong
    [J]. CHEMICAL COMMUNICATIONS, 2009, (33) : 5021 - 5023
  • [10] Inter- and intramolecular addition/cyclizations of sulfonamide anions with alkynyliodonium triflates. Synthesis of dihydropyrrole, pyrrole, indole, and tosylenamide heterocycles
    Feldman, KS
    Bruendl, MM
    Schildknegt, K
    Bohnstedt, AC
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) : 5440 - 5452