Iridium-Catalyzed Formal [4+1] Annulation of Benzamides and Cyclopropanols to Afford Isoindolin-1-one Derivatives via C-H Activation

被引：1

作者：

Xu, Shuran ^{[1
,2
,3
]}

Luo, Cankun ^{[2
,3
]}

Yan, Kaichuan ^{[2
,3
]}

Li, Jianglian ^{[2
,3
]}

Lai, Ruizhi ^{[2
,3
]}

Hai, Li ^{[2
,3
]}

Guan, Mei ^{[1
]}

Wu, Yong ^{[2
,3
]}

机构：

[1] Sichuan Univ, West China Hosp, Chengdu 610041, Peoples R China

[2] Sichuan Univ, West China Sch Pharm, Key Lab Drug Targeting & Drug Delivery Syst, Educ Minist, 17 Southern Renmin Rd, Chengdu 610041, Sichuan, Peoples R China

[3] Sichuan Univ, West China Sch Pharm, Dept Med Chem, 17 Southern Renmin Rd, Chengdu 610041, Sichuan, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2022年 / 54卷 / 13期

基金：

中国国家自然科学基金;

关键词：

C-H activation; benzamides; cyclopropanols; C-N bond formation; isoindolin-1-ones; RING EXPANSION; FUNCTIONALIZATION; ARYLATION; EFFICIENT;

D O I：

10.1055/a-1780-1935

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An iridium-catalyzed reaction protocol has been developed to achieve the oxidative C-H/N-H annulation of benzamides with cyclopropanols as C1 synthon. Structurally diverse isoindolin-1-ones were furnished via sequential C-H/C-C cleavage and C-C/C-N bond formation.

引用

页码：3015 / 3024

页数：10

共 38 条

[11] Nonpeptide Urotensin-II Receptor Antagonists: A New Ligand Class Based on Piperazino-Phthalimide and Piperazino-Isoindolinone Subunits [J].

Lawson, Edward C. ;

Luci, Diane K. ;

Ghosh, Shyamali ;

Kinney, William A. ;

Reynolds, Charles H. ;

Qi, Jenson ;

Smith, Charles E. ;

Wang, Yuanping ;

Minor, Lisa K. ;

Haertlein, Barbara J. ;

Parry, Tom J. ;

Damiano, Bruce P. ;

Maryanoff, Bruce E. .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (23) :7432-7445

[12] Transition-metal-catalyzed transformations of C-N single bonds: Advances in the last five years, challenges and prospects [J].

Liu, Jun ;

Yang, Yong ;

Ouyang, Kunbing ;

Zhang, Wen-Xiong .

GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (02) :87-122

[13] C-H Activation versus Ring Opening and Inner-versus Outer-Sphere Concerted Metalation-Deprotonation in Rh(III)-Catalyzed Oxidative Coupling of Oxime Ether and Cyclopropanol: A Density Functional Theory Study [J].

Meng, Ran ;

Bi, Siwei ;

Jiang, Yuan-Ye ;

Liu, Yuxia .

JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (17) :11150-11160

[14] Catalytic asymmetric umpolung reaction of imines to synthesize isoindolinones and tetrahydroisoquinolines [J].

Mou, Ze-Dong ;

Zhang, Xia ;

Niu, Dawen .

GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (01) :70-73

[15] Transition-metal-catalyzed reactions in heterocyclic synthesis [J].

Nakamura, I ;

Yamamoto, Y .

CHEMICAL REVIEWS, 2004, 104 (05) :2127-2198

[16] Hydroxorhodium/Chiral Diene Complexes as Effective Catalysts for the Asymmetric Arylation of 3-Aryl-3-hydroxyisoindolin-1-ones [J].

Nishimura, Takahiro ;

Noishiki, Akira ;

Ebe, Yusuke ;

Hayashi, Tamio .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (06) :1777-1780

[17] Oxidizing Directing Groups Enable Efficient and Innovative C-H Activation Reactions [J].

Patureau, Frederic W. ;

Glorius, Frank .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (09) :1977-1979

[18] Synthesis of indoles, indolines, and carbazoles via palladium-catalyzed C-H activation [J].

Rago, Alexander J. ;

Dong, Guangbin .

GREEN SYNTHESIS AND CATALYSIS, 2021, 2 (02) :216-227

[19] Analysis of Chemical Shift Changes Reveals the Binding Modes of Isoindolinone Inhibitors of the MDM2-p53 Interaction [J].

Riedinger, Christiane ;

Endicott, Jane A. ;

Kemp, Stuart J. ;

Smyth, Lynette A. ;

Watson, Anna ;

Valeur, Eric ;

Golding, Bernard T. ;

Griffin, Roger J. ;

Hardcastle, Ian R. ;

Noble, Martin E. ;

McDonnell, James M. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (47) :16038-16044

[20] Synthesis of α-indanones via intramolecular direct arylation with cyclopropanol-derived homoenolates [J].

Rosa, David ;

Orellana, Arturo .

CHEMICAL COMMUNICATIONS, 2012, 48 (13) :1922-1924

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