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

页码：2051 / 2056

页数：6

共 45 条

[1] Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions [J].

Bellina, Fabio ;

Rossi, Renzo .

TETRAHEDRON, 2006, 62 (31) :7213-7256

[2] A highly active catalyst for Suzuki-Miyaura cross-coupling reactions of heteroaryl compounds [J].

Billingsley, Kelvin L. ;

Anderson, Kevin W. ;

Buchwald, Stephen L. .

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 [J].

Brawn, Ryan A. ;

Panek, James S. .

ORGANIC LETTERS, 2009, 11 (02) :473-476

[4] Small-molecule inhibitors of protein geranylgeranyltransferase type I [J].

Castellano, Sabrina ;

Fiji, Hannah D. G. ;

Kinderman, Sape S. ;

Watanabe, Masaru ;

de Leon, Pablo ;

Tamanoi, Fuyuhiko ;

Kwon, Ohyun .

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 [J].

Chen, Zhengwang ;

Huang, Gao ;

Jiang, Huanfeng ;

Huang, Huawen ;

Pan, Xiaoyan .

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 [J].

Cheng, Jiajia ;

Jiang, Xuefeng ;

Zhu, Can ;

Ma, Shengming .

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 [J].

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. .

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 [J].

Ding, CH ;

Dai, LX ;

Hou, XL .

TETRAHEDRON, 2005, 61 (40) :9586-9593

[9] Facile construction of highly functionalized 2-pyrrolines via FeCl3-catalyzed reaction of aziridines with arylalkynes [J].

Fan, Jinmin ;

Gao, Linfeng ;

Wang, Zhiyong .

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 [J].

Feldman, KS ;

Bruendl, MM ;

Schildknegt, K ;

Bohnstedt, AC .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) :5440-5452

← 1 2 3 4 5 →