Palladium-Catalyzed [2+2+2] Annulation via Transformations of Multiple C-H Bonds: One-Pot Synthesis of Diverse Indolo[3,2-a]carbazoles

被引：36

作者：

Kumar, K. Shiva ^{[1
]}

Meesa, Siddi Ramulu ^{[1
]}

Naikawadi, Praveen Kumar ^{[1
]}

机构：

[1] Osmania Univ, Dept Chem, Hyderabad 500007, Telangana, India

来源：

ORGANIC LETTERS | 2018年 / 20卷 / 19期

关键词：

COLLECTIVE TOTAL-SYNTHESIS; CARBON-HYDROGEN BONDS; CARBAZOLE ALKALOIDS; INTERNAL ALKYNES; OXIDATIVE ANNULATION; EFFICIENT SYNTHESIS; FUNCTIONALIZATION; ACTIVATION; INDOLES; DERIVATIVES;

D O I：

10.1021/acs.orglett.8b02465

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A Pd-catalyzed novel cascade reaction has been developed for the synthesis of indolo[3,2a]carbazoles involving multiple C-H transformation-annulations between the indoles and alkynes. The method involves molecular oxygen as the sole oxidant and is an effective and step-economic process.

引用

页码：6079 / 6083

页数：5

共 43 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Ruthenium-Catalyzed C-H/N-O Bond Functionalization: Green Isoquinolone Syntheses in Water [J].

Ackermann, Lutz ;

Fenner, Sabine .

ORGANIC LETTERS, 2011, 13 (24) :6548-6551

[3] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope [J].

Ackermann, Lutz .

CHEMICAL REVIEWS, 2011, 111 (03) :1315-1345

[4] Palladium-Catalyzed Tandem Regioselective Oxidative Coupling from Indoles and Maleimides: One-Pot Synthesis of Indolopyrrolocarbazoles and Related Indolylmaleimides [J].

An, Yu-Long ;

Yang, Zhen-Hua ;

Zhang, He-Hui ;

Zhao, Sheng-Yin .

ORGANIC LETTERS, 2016, 18 (02) :152-155

[5] Weak Directing Group Steered Formal Oxidative [2+2+2]-Cyclization for Selective Benzannulation of Indoles [J].

Bettadapur, Kiran R. ;

Kapanaiah, Raja ;

Lanke, Veeranjaneyulu ;

Prabhu, Kandikere Ramaiah .

JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04) :1810-1818

[6] Poly(2,7-carbazole)s: Structure-property relationships [J].

Blouin, Nicolas ;

Leclerc, Mario .

ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (09) :1110-1119

[7] The medicinal chemist's toolbox for late stage functionalization of drug-like molecules [J].

Cernak, Tim ;

Dykstra, Kevin D. ;

Tyagarajan, Sriram ;

Vachal, Petr ;

Krska, Shane W. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (03) :546-576

[8] Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds [J].

Daugulis, Olafs ;

Roane, James ;

Tran, Ly Dieu .

ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) :1053-1064

[9] Mild metal-catalyzed C-H activation: examples and concepts [J].

Gensch, T. ;

Hopkinson, M. N. ;

Glorius, F. ;

Wencel-Delord, J. .

CHEMICAL SOCIETY REVIEWS, 2016, 45 (10) :2900-2936

[10] Palladium-catalyzed dehydrogenative annulation of imidazo[1,2-a]pyridines with diarylalkynes [J].

Ghosh, Monoranjan ;

Naskar, Aswini ;

Mishra, Subhajit ;

Hajra, Alakananda .

TETRAHEDRON LETTERS, 2015, 56 (27) :4101-4104

← 1 2 3 4 5 →