A Synthesis of 1H-Indazoles via a Cu(OAc)2-Catalyzed N-N Bond Formation

被引：63

作者：

Chen, Cheng-yi ^{[1
]}

Tang, Guangrong ^{[2
]}

He, Fengxian ^{[2
]}

Wang, Zhaobin ^{[2
]}

Jing, Hailin ^{[2
]}

Faessler, Roger ^{[1
]}

机构：

[1] Cilag AG, Small Mol API Switzerland, Pharmaceut Dev & Mfg Sci, Janssen R&D, Hochstr 201, CH-8205 Schaffhausen, Switzerland

[2] Porton Shanghai R&D Ctr, 1299 Ziyue Rd,Zizhu Sci Pk, Shanghai 200241, Peoples R China

来源：

ORGANIC LETTERS | 2016年 / 18卷 / 07期

关键词：

INDAZOLE-TYPE ALKALOIDS; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; NIGELLA-SATIVA; H AMIDATION; IN-VITRO; DERIVATIVES; BENZYDAMINE; SEEDS; FUNCTIONALIZATION;

D O I：

10.1021/acs.orglett.6b00611

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis of 1H-indazoles featuring a Cu(OAc)(2)-catalyzed N-N bond formation using oxygen as the terminal oxidant is described. The reaction of readily available 2-aminobenzonitriles with various organometallic reagents led to o-aminoaryl N-H ketimine species. The subsequent Cu(OAc)(2)-catalyzed N-N bond formation in DMSO under oxygen afforded a wide variety of 1H-indazoles in good to excellent yields.

引用

页码：1690 / 1693

页数：4

共 42 条

[11] A practical, metal-free synthesis of 1H-indazoles [J].

Counceller, Carla M. ;

Eichman, Chad C. ;

Wray, Brenda C. ;

Stambuli, James P. .

ORGANIC LETTERS, 2008, 10 (05) :1021-1023

[12] Synthesis of o-(Dimethylamino)aryl Ketones, Acridones, Acridinim Salts, and 1H-Indazoles by the Reaction of Hydrazones and Arynes [J].

Dubrovskiy, Anton V. ;

Larock, Richard C. .

JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (24) :11232-11256

[13] Design, synthesis, and biological evaluations of novel quinolones as HIV-1 non-nucleoside reverse transcriptase inhibitors [J].

Ellis, David ;

Kuhen, Kelli L. ;

Anaclerio, Beth ;

Wu, Baogen ;

Wolff, Karen ;

Yin, Hong ;

Bursulaya, Badry ;

Caldwell, Jeremy ;

Karanewsky, Donald ;

He, Yun .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (16) :4246-4251

[14] Synthesis of indazole motifs and their medicinal importance: An overview [J].

Gaikwad, Digambar D. ;

Chapolikar, Archana D. ;

Devkate, Chandrashekhar G. ;

Warad, Khandu D. ;

Tayade, Amit P. ;

Pawar, Rajendra P. ;

Domb, Abraham J. .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 90 :707-731

[15]

George I. G., 2009, U.S. Patent, Patent No. 20090197911

[16] Copper-Catalyzed C-H Functionalization Reactions: Efficient Synthesis of Heterocycles [J].

Guo, Xun-Xiang ;

Gu, Da-Wei ;

Wu, Zhengxing ;

Zhang, Wanbin .

CHEMICAL REVIEWS, 2015, 115 (03) :1622-1651

[17] Copper(II) Acetate/Oxygen-Mediated Nucleophilic Addition and Intramolecular C-H Activation/C-N or C-C Bond Formation: One-Pot Synthesis of Benzimidazoles or Quinazolines [J].

He, Hua-Feng ;

Wang, Zhi-Jing ;

Bao, Weiliang .

ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (17) :2905-2912

[18] Facile One-Pot Synthesis of [1,2,3] Triazolo[ 1, 5-a] Pyridines from 2Acylpyridines by Copper(II)-Catalyzed Oxidative N-N Bond Formation [J].

Hirayama, Tasuku ;

Ueda, Satoshi ;

Okada, Takahiro ;

Tsurue, Norihiko ;

Okuda, Kensuke ;

Nagasawa, Hideko .

CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (14) :4156-4162

[19] A general and efficient approach to 2H-indazoles and 1H-pyrazoles through copper-catalyzed intramolecular N-N bond formation under mild conditions [J].

Hu, Jiantao ;

Cheng, Yongfeng ;

Yang, Yiqing ;

Rao, Yu .

CHEMICAL COMMUNICATIONS, 2011, 47 (36) :10133-10135

[20] Copper-Catalyzed Intramolecular Oxidative C(sp3)- H Amidation of 2-Aminoacetophenones: Efficient Synthesis of Indoline-2,3-diones [J].

Huang, Jinbo ;

Mao, Tingting ;

Zhu, Qiang .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (14) :2878-2882

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