Cu (I)-Catalyzed Synthesis of Polysubstituted Pyrroles from Dialkyl Ethylenedicarboxylates and β-Enamino Ketones or Esters in the Presence of O2

被引：168

作者：

Yan, Ru-Long ^{[1
]}

Luo, Jia ^{[1
]}

Wang, Chuan-Xin ^{[1
]}

Ma, Chao-Wei ^{[1
]}

Huang, Guo-Sheng ^{[1
]}

Liang, Yong-Min ^{[1
]}

机构：

[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 15期

基金：

美国国家科学基金会;

关键词：

ONE-POT; 1,3-DICARBONYL COMPOUNDS; PROPARGYLIC ALCOHOLS; SUBSTITUTED PYRROLES; EFFICIENT SYNTHESIS; DERIVATIVES; ALKALOIDS; CONSTRUCTION; CHEMISTRY; NINGALIN;

D O I：

10.1021/jo101022k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A straightforward method for the synthesis of polysubstituted pyrroles was achieved easily from oxidative cyclization of beta-enamino ketones or esters and alkynoates catalyzed by CuI in the presence of O-2.

引用

页码：5395 / 5397

页数：3

共 63 条

[51]

Shu X., 2008, ADV SYNTH CATAL, V350, P313

[52] Formation of pyridazinium salts by azo coupling of N-substituted 3-amino-1-phenylbut-2-en-1-ones and diazonium salts [J].

Simunek, P ;

Pesková, M ;

Bertolasi, V ;

Lycka, A ;

Machácek, V .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (24) :5055-5063

[53] A new use of Wittig-type reagents as 1,3-dipolar cycloaddition precursors and in pyrrole synthesis [J].

St. Cyr, Daniel J. ;

Arndtsen, Bruce A. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) :12366-+

[54] Palladium oxidase catalysis: Selective oxidation of organic chemicals by direct dioxygen-coupled turnover [J].

Stahl, SS .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (26) :3400-3420

[55]

Sundberg R.J., 1996, COMPREHENSIVE HETERO, V2, P119, DOI DOI 10.1016/B978-008096518-5.00042-3

[56] A diversity-oriented strategy for the construction of tetrasubstituted pyrroles via coupled domino processes [J].

Tejedor, D ;

González-Cruz, D ;

García-Tellado, F ;

Marrero-Tellado, JJ ;

Rodríguez, ML .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (27) :8390-8391

[57] From Conjugated Tertiary Skipped Diynes to Chain-Functionalized Tetrasubstituted Pyrroles [J].

Tejedor, David ;

Lopez-Tosco, Sara ;

Gonzalez-Platas, Javier ;

Garcia-Tellado, Fernando .

CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (04) :838-842

[58] Biological formation of pyrroles: Nature's logic and enzymatic machinery [J].

Walsh, Christopher T. ;

Garneau-Tsodikova, Sylvie ;

Howard-Jones, Annaleise R. .

NATURAL PRODUCT REPORTS, 2006, 23 (04) :517-531

[59] The Synthesis of Polysubstituted Pyrroles via the Coupling of Phenyliodonium Ylides and Enamine Esters [J].

Wang, Jun-Yan ;

Wang, Xian-Pei ;

Yu, Zheng-Sen ;

Yu, Wei .

ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (13) :2063-2066

[60] Cross-coupling reactions in the chemistry of silole-containing π-conjugated oligomers and polymers [J].

Yamaguchi, S ;

Tamao, K .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2002, 653 (1-2) :223-228

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