Pd-Catalyzed C-H Halogenation of Indolines and Tetrahydroquinolines with Removable Directing Group

被引：30

作者：

Ahmad, Ashfaq ^{[1
]}

Dutta, Himangsu Sekhar ^{[2
]}

Kumar, Mohit ^{[2
]}

Khan, Afsar Ali ^{[2
]}

Raziullah ^{[1
]}

Koley, Dipankar ^{[1
,2
]}

机构：

[1] CSIR Cent Drug Res Inst, Med & Proc Chem Div, Lucknow 226031, Uttar Pradesh, India

[2] Acad Sci & Innovat Res, New Delhi 110001, India

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 15期

关键词：

ORTHO-SELECTIVE HALOGENATION; QUINOLINE N-OXIDES; REGIOSELECTIVE HALOGENATION; BOND HALOGENATION; LITHIUM HALIDES; C-7; POSITION; ARENES; FUNCTIONALIZATION; BROMINATION; ALKYLATION;

D O I：

10.1021/acs.orglett.0c01963

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pd-catalyzed directing-group-assisted regioselective halogenations to C7 of indolines and C8 of tetrahydroquinolines were achieved in good to excellent yields. The practicality and utility of the developed method have been illustrated by various functional group transformations such as arylation, alkenylation, cyanation, and silylation utilizing the installed synthetic handle. The concise synthesis of primaquine, an antimalarial drug, and formal syntheses of two bioactive natural products, hippadine and pratosine, have also been demonstrated.

引用

页码：5870 / 5875

页数：6

共 108 条

[51] Selective C-H Halogenation with a Highly Fluorinated Manganese Porphyrin [J].

Li, Gang ;

Dilger, Andrew K. ;

Cheng, Peter T. ;

Ewing, William R. ;

Groves, John T. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (05) :1251-1255

[52] Rh(III)-Catalyzed direct C-7 amination of indolines with anthranils [J].

Li, Haoyi ;

Jie, Jiyang ;

Wu, Songxiao ;

Yang, Xiaobo ;

Xu, Hao .

ORGANIC CHEMISTRY FRONTIERS, 2017, 4 (02) :250-254

[53] The antitumor activity of zinc(II) and copper(II) complexes with 5,7-dihalo-substituted-8-quinolinoline [J].

Liu, Yan-Cheng ;

Wei, Jian-Hua ;

Chen, Zhen-Feng ;

Liu, Mei ;

Gu, Yun-Qiong ;

Huang, Ke-Bin ;

Li, Zhu-Quan ;

Liang, Hong .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2013, 69 :554-563

[54] Halogen Bonding-A Novel Interaction for Rational Drug Design? [J].

Lu, Yunxiang ;

Shi, Ting ;

Wang, Yong ;

Yang, Huaiyu ;

Yan, Xiuhua ;

Luo, Xiaoming ;

Jiang, Hualiang ;

Zhu, Weiliang .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (09) :2854-2862

[55] Direct and site-selective Pd(II)-catalyzed C-7 arylation of indolines with arylsilanes [J].

Luo, Haiqing ;

Liu, Haidong ;

Zhang, Zhipeng ;

Xiao, Yifan ;

Wang, Sihui ;

Luo, Xuzhong ;

Wang, Kejun .

RSC ADVANCES, 2016, 6 (45) :39292-39295

[56] [Cp*RhIII]/Ionic Liquid as a Highly Efficient and Recyclable Catalytic Medium for C-H Amidation [J].

Ma, Qiang ;

Yu, Xinling ;

Lai, Ruizhi ;

Lv, Songyang ;

Dai, Weiyang ;

Zhang, Chen ;

Wang, Xiaolong ;

Wang, Qiantao ;

Wu, Yong .

CHEMSUSCHEM, 2018, 11 (20) :3672-3678

[57] Isothiocyanate-Directed Ortho-Selective Halogenation of Arenes via C-H Functionalization [J].

Mandapati, Usharani ;

Pinapati, Srinivasarao ;

Tamminana, Ramana ;

Rameshraju, Rudraraju .

CATALYSIS LETTERS, 2018, 148 (01) :418-423

[58] PdII-catalyzed monoselective ortho halogenation of C-H bonds assisted by counter cations:: A complementary method to directed ortho lithiation [J].

Mei, Tian-Sheng ;

Giri, Ramesh ;

Maugel, Nathan ;

Yu, Jin-Quan .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (28) :5215-5219

[59] Quinoline, quinazoline and acridone alkaloids [J].

Michael, Joseph P. .

NATURAL PRODUCT REPORTS, 2008, 25 (01) :166-187

[60] Rhodium-Catalyzed sp2 C-H Acetoxylation of N-Aryl Azaindoles/N-Heteroaryl Indolines [J].

Mishra, Aniket ;

Vats, Tripta Kumari ;

Nair, Mahesh P. ;

Das, Arindam ;

Deb, Indubhusan .

JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (23) :12406-12415

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