Rh(III)-Catalyzed Domino [4+2] Annulation/Aza-Michael Addition of N-(Pivaloyloxy)benzamides with 1,5-Enynes via C-H Activation: Synthesis of Functionalized Aromathecins

被引：20

作者：

Reddy, Chada Raji ^{[1
,2
]}

Mallesh, Kathe ^{[1
,2
]}

Bodasu, Srinivas ^{[1
]}

Donthiri, Ramachandra Reddy ^{[1
]}

机构：

[1] CSIR, Dept Organ Synth & Proc Chem, Indian Inst Chem Technol CSIR IICT, Hyderabad 500007, India

[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 12期

关键词：

CASCADE ANNULATION; DIRECTING GROUP; CYCLIZATION; ACCESS; ISOQUINOLINES; INHIBITORS; ALKYNES;

D O I：

10.1021/acs.joc.0c00615

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reported herein are the Rh(III)-catalyzed cascade annulation reactions of N-(pivaloyloxy)benzamides with 1,5-enynes to access diversely substituted aromathecin derivatives involving C-H activation. The developed procedure offers an efficient synthetic tool for the assembly of a wide range of N-(pivaloyloxy)-benzamides and 1,5-enynes with good atom economy and functional group tolerance. The key reactions involved in this annulation are alkyne insertion and aza-Michael addition under oxidant-free mild reaction conditions.

引用

页码：7905 / 7915

页数：11

共 53 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] Transition metal-catalyzed C-H bond functionalizations by the use of diverse directing groups [J].

Chen, Zhengkai ;

Wang, Binjie ;

Zhang, Jitan ;

Yu, Wenlong ;

Liu, Zhanxiang ;

Zhang, Yuhong .

ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (09) :1107-1295

[3] Design, synthesis, and biological evaluation of 14-substituted aromathecins as topoisomerase I inhibitors [J].

Cinelli, Maris A. ;

Morrell, Andrew ;

Dexheimer, Thomas S. ;

Scher, Evan S. ;

Pommier, Yves ;

Cushman, Mark .

JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4609-4619

[4] Expeditious Synthesis of the Topoisomerase I Inhibitors Isoindolo-[2,1-b]isoquinolin-7(5H)-one and the Alkaloid Rosettacin Based on Aryl Radical Cyclization of Enamide Generated by Using N-Acyl-iminium Chemistry [J].

El Blidi, Lahssen ;

Namoune, Aurelie ;

Bridoux, Alexandre ;

Nimbarte, Vijaykumar D. ;

Lawson, Ata Martin ;

Comesse, Sebastien ;

Daich, Adam .

SYNTHESIS-STUTTGART, 2015, 47 (22) :3583-3592

[5] Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C-H Activation [J].

Fukui, Yuki ;

Liu, Ping ;

Liu, Qiang ;

He, Zhi-Tao ;

Wu, Nuo-Yi ;

Tian, Ping ;

Lin, Guo-Qiang .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (44) :15607-15614

[6] Versatile Synthesis of Isoquinolines and Isochromenes by Pd-Catalyzed Oxidative Carbonylation of (2-Alkynyl)benzylideneamine Derivatives [J].

Gabriele, Bartolo ;

Veltri, Lucia ;

Maltese, Vito ;

Spina, Rosella ;

Mancuso, Raffaella ;

Salerno, Giuseppe .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (28) :5626-5635

[7] Rh[III]-Catalyzed Direct C-H Amination Using N-Chloroamines at Room Temperature [J].

Grohmann, Christoph ;

Wang, Honggen ;

Glorius, Frank .

ORGANIC LETTERS, 2012, 14 (02) :656-659

[8] Rhodium(III)-Catalyzed Heterocycle Synthesis Using an Internal Oxidant: Improved Reactivity and Mechanistic Studies [J].

Guimond, Nicolas ;

Gorelsky, Serge I. ;

Fagnou, Keith .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (16) :6449-6457

[9] Metal-Catalyzed Annulations through Activation and Cleavage of C-H Bonds [J].

Gulias, Moises ;

Luis Mascarenas, Jose .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (37) :11000-11019

[10] Platinum oxide catalyzed hydrosilylation of unsymmetrical internal aryl alkynes under ortho-substituent regiocontrol [J].

Hamze, A ;

Provot, O ;

Alami, M ;

Brion, JD .

ORGANIC LETTERS, 2005, 7 (25) :5625-5628

← 1 2 3 4 5 6 →