Copper-Catalyzed [4+1] and [4+2] Reactions through Tandem Remote Propargylation/Cyclization/Isomerization with an Amine or a Hydrazine

被引：3

作者：

Sun, Yu-Ze ^{[1
,2
,3
]}

Lin, Guo-Qiang ^{[1
,2
]}

He, Zhi-Tao ^{[3
,4
,5
]}

机构：

[1] Shanghai Normal Univ, Dept Chem, Shanghai 200234, Peoples R China

[2] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Chem Biol, Shanghai 200032, Peoples R China

[3] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[4] Univ Chinese Acad Sci, Hangzhou Inst Adv Study, Sch Chem & Mat Sci, Hangzhou 310024, Peoples R China

[5] Ningbo Zhongke Creat Ctr New Mat, Ningbo 315899, Peoples R China

来源：

SYNLETT | 2025年 / 36卷 / 01期

关键词：

copper catalysis; propargylic substitution; 4+1] cyclization; 4+2] cyclization; arylhydrazines; amines; PROPARGYLIC SUBSTITUTION-REACTIONS; ENANTIOSELECTIVE PROPARGYLATION; POTENT; ESTERS; CYCLOADDITION; CONSTRUCTION; HETEROCYCLES; ANNULATION; INHIBITORS; DISCOVERY;

D O I：

10.1055/a-2294-5395

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two novel copper-catalyzed cyclization reactions involvinga remote propargylic substitution/cyclization/isomerization cascade aredisclosed. Derivatives of the seldomly studied heterocycles thieno[2,3-c]pyrrole and thieno[2,3-d]pyridazine are conveniently synthesized inmoderate to good yields from primary amines or arylhydrazinesthrough [4+1] and [4+2] reactions, respectively. Preliminary mechanis-tic experiments corroborated the occurrence of the designed cascadereactions

引用

页码：82 / 86

页数：5

共 61 条

[51] Analysis of the Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among US FDA Approved Pharmaceuticals [J].

Vitaku, Edon ;

Smith, David T. ;

Njardarson, Jon T. .

JOURNAL OF MEDICINAL CHEMISTRY, 2014, 57 (24) :10257-10274

[52] De Novo Construction of Chiral Aminoindolines by Cu-Catalyzed Asymmetric Cyclization and Subsequent Discovery of an Unexpected Sulfonyl Migration [J].

Wang, Bao-Cheng ;

Fan, Tingting ;

Xiong, Fen-Ya ;

Chen, Peng ;

Fang, Kai-Xin ;

Tan, Ying ;

Lu, Liang-Qiu ;

Xiao, Wen-Jing .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (43) :19932-19941

[53] Catalytic Asymmetric [4+1] Annulation of Sulfur Ylides with Copper-Allenylidene Intermediates [J].

Wang, Qiang ;

Li, Tian-Ren ;

Lu, Liang-Qiu ;

Li, Miao-Miao ;

Zhang, Kai ;

Xiao, Wen-Jing .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2016, 138 (27) :8360-8363

[54] Highly Enantioselective Catalytic Vinylogous Propargylation of Coumarins Yields a Class of Autophagy Inhibitors [J].

Xu, Hao ;

Laraia, Luca ;

Schneider, Laura ;

Louven, Kathrin ;

Strohmann, Carsten ;

Antonchick, Andrey P. ;

Waldmann, Herbert .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (37) :11232-11236

[55] Coupling reactions and coupling-alkylations of thiophenecarbaldehydes promoted by samarium diiodide [J].

Yang, SM ;

Fang, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (02) :394-399

[56] Recent advances in copper-catalyzed decarboxylative reactions of propargylic cyclic carbonates/carbamates [J].

You, Yong ;

Zhang, Yan-Ping ;

Wang, Zhen-Hua ;

Zhao, Jian-Qiang ;

Yin, Jun-Qing ;

Yuan, Wei-Cheng .

CHEMICAL COMMUNICATIONS, 2023, 59 (49) :7483-7505

[57] Highly Diastereo- and Enantioselective Cu-Catalyzed [3+3] Cycloaddition of Propargyl Esters with Cyclic Enamines toward Chiral Bicyclo[n.3.1] Frameworks [J].

Zhang, Cheng ;

Hu, Xin-Hu ;

Wang, Ya-Hui ;

Zheng, Zhuo ;

Xu, Jie ;

Hu, Xiang-Ping .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (23) :9585-9588

[58] Recent advances in copper-catalyzed propargylic substitution [J].

Zhang, De-Yang ;

Hu, Xiang-Ping .

TETRAHEDRON LETTERS, 2015, 56 (02) :283-295

[59] Enantioconvergent Copper Catalysis: In Situ Generation of the Chiral Phosphorus Ylide and Its Wittig Reactions [J].

Zhang, Kai ;

Lu, Liang-Qiu ;

Yao, Sheng ;

Chen, Jia-Rong ;

Shi, De-Qing ;

Xiao, Wen-Jing .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (36) :12847-12854

[60] N-Heterocyclic Carbene/Copper Cooperative Catalysis for the Asymmetric Synthesis of Spirooxindoles [J].

Zhang, Zi-Jing ;

Zhang, Ling ;

Geng, Rui-Long ;

Song, Jin ;

Chen, Xiao-Hua ;

Gong, Liu-Zhu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (35) :12190-12194

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