Catalytic Dual 1,1-H-Abstraction/Insertion for Domino Spirocyclizations

被引：224

作者：

Qiu, Jiang-Kai ^{[1
,2
]}

Jiang, Bo ^{[1
]}

Zhu, Yi-Long ^{[1
,2
]}

Hao, Wen-Juan ^{[1
]}

Wang, De-Cai ^{[2
]}

Sun, Jun ^{[1
,2
]}

Wei, Ping ^{[2
]}

Tu, Shu-Jiang ^{[1
]}

Li, Guigen ^{[3
,4
]}

机构：

[1] Jiangsu Normal Univ, Jiangsu Key Lab Green Synthet Chem Funct Mat, Sch Chem & Chem Engn, Xuzhou 221116, Peoples R China

[2] Nanjing Tech Univ, Biotechnol & Pharmaceut Engn, Nanjing 210009, Jiangsu, Peoples R China

[3] Nanjing Univ, Collaborat Innovat Ctr Chem Life Sci, Inst Chem & BioMed Sci, Nanjing 210093, Jiangsu, Peoples R China

[4] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 28期

关键词：

SP(3) C-H; BARBITURIC-ACIDS; REDUCTIVE CYCLIZATION; HETEROCYCLE SYNTHESIS; STRUCTURAL-ANALYSIS; BOND FORMATION; CYCLOISOMERIZATION; C(SP(3))-H; FUNCTIONALIZATION; ACTIVATION;

D O I：

10.1021/jacs.5b05735

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A catalytic domino spirocyclization of 1,7-enynes with simple cycloalkanes and Cyclo-1,3-dicarbonyls has been established via multiple C-C bond formations from alkynyl/alkenyl functions and dual alpha,alpha-C(sp(3))-H abstractibn/insertion The reaction involves addition, 6-exo-dig cyclization and radical coupling sequences under convenient catalytic conditions and provides a concise access to spiro cyclopenta[c]quinolines in good to excellent yields.

引用

页码：8928 / 8931

页数：4

共 75 条

[51] Catalytic Functionalization of C(sp2)-H and C(sp3)-H Bonds by Using Bidentate Directing Groups [J].

Rouquet, Guy ;

Chatani, Naoto .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (45) :11726-11743

[52] Catalytic functionalization of unactivated primary C-H bonds directed by an alcohol [J].

Simmons, Eric M. ;

Hartwig, John F. .

NATURE, 2012, 483 (7387) :70-73

[53] Synthesis of highly functionalized barbituric acids and study of their interactions with p-glycoprotein and Mg2+ - Potential candidates for multi drug resistance modulation [J].

Singh, Palwinder ;

Kaur, Jatinder ;

Bhardwaj, Atul .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (03) :1256-1262

[54] Iron-Catalyzed, Hydrogen-Mediated Reductive Cyclization of 1,6-Enynes and Diynes: Evidence for Bis(imino)pyridine Ligand Participation [J].

Sylvester, Kevin T. ;

Chirik, Paul J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (25) :8772-+

[55] Switching between Reaction Pathways by an Alcohol Cosolvent Effect: SmI2-Ethylene Glycol vs SmI2-H2O Mediated Synthesis of Uracils [J].

Szostak, Michal ;

Spain, Malcolm ;

Sautier, Brice ;

Procter, David J. .

ORGANIC LETTERS, 2014, 16 (21) :5694-5697

[56] Structural analysis and reactivity of unusual tetrahedral intermediates enabled by SmI2-mediated reduction of barbituric acids: vinylogous N-acyliminium additions to α-hydroxy-N-acyl-carbamides [J].

Szostak, Michal ;

Sautier, Brice ;

Procter, David J. .

CHEMICAL COMMUNICATIONS, 2014, 50 (19) :2518-2521

[57] Selective Reduction of Barbituric Acids Using SmI2/H2O: Synthesis, Reactivity, and Structural Analysis of Tetrahedral Adducts [J].

Szostak, Michal ;

Sautier, Brice ;

Spain, Malcolm ;

Behlendorf, Maike ;

Procter, David J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (48) :12559-12563

[58]

Tietze L.F., 2006, Domino Reactions in Organic Synthesis

[59]

Tietze L.F., 2014, Domino Reactions, DOI DOI 10.1021/ol402473m

[60] A NOVEL NICKEL-CHROMIUM CATALYST SYSTEM FOR CYCLIZATION VIA INTRAMOLECULAR CARBAMETALATION [J].

TROST, BM ;

TOUR, JM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (17) :5268-5270

← 1 2 3 4 5 6 7 8 →