Synthesis of Tetrahydroindole Derivatives via Metal-Free Intramolecular [4+2] Annulation of Ynamides

被引：1

作者：

Zhang Zhixin ^{[1
]}

Zhai Tongyi ^{[1
]}

Zhu Bohan ^{[2
]}

Qian Pengcheng ^{[2
]}

Ye Longwu ^{[1
,3
]}

机构：

[1] Xiamen Univ, Coll Chem & Chem Engn, Xiamen 361005, Fujian, Peoples R China

[2] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Zhejiang, Peoples R China

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

来源：

CHINESE JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 42卷 / 05期

基金：

中国国家自然科学基金;

关键词：

annulation reaction; metal-free catalysis; ynamides; heterocycle synthesis; DIELS-ALDER REACTION; CYCLOADDITION; CATALYST; COMPLEX; ACCESS; POWERFUL; SYSTEM; ALKYNE;

D O I：

10.6023/cjoc202201006

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A metal-free reaction of 4-siloxy-3,5-diene ynamides via an intramolecular [4+2] annulation has been developed. In the presence of catalytic Et3N, this protocol leads to the facile formation of six-membered cycloadducts. This reaction can proceed smoothly under mild condition without transition-metal-catalysts and its substrate scope is wide. This strategy provides a concise and practical protocol to synthesize natural product and bioactive compounds containing 4-hydroxyl hydroindole skeletons.

引用

页码：1501 / 1508

页数：8

共 83 条

[11]

Evano G, 2015, ALDRICHIM ACTA, V48, P59

[12] Bicyclic Guanidine Catalyzed Asymmetric Tandem Isomerization Intramolecular-Diels-Alder Reaction: The First Catalytic Enantioselective Total Synthesis of (+)-alpha-Yohimbine [J].

Feng, Wei ;

Jiang, Danfeng ;

Kee, Choon-Wee ;

Liu, Hongjun ;

Tan, Choon-Hong .

CHEMISTRY-AN ASIAN JOURNAL, 2016, 11 (03) :390-394

[13] Sulfoxide-Directed Intramolecular [4+2] Cycloadditions between 2-Sulfinyl Butadienes and Unactivated Alkynes [J].

Fernandez de la Pradilla, Roberto ;

Tortosa, Mariola ;

Castellanos, Esther ;

Viso, Alma ;

Baile, Raquel .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (05) :1517-1533

[14] Two manifolds for metal-catalyzed intramolecular Diels-Alder reactions of unactivated alkynes [J].

Fuerstner, Alois ;

Stimson, Christopher C. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) :8845-8849

[15] The Diels-Alder reaction: A powerful tool for the design of drug delivery systems and biomaterials [J].

Gregoritza, Manuel ;

Brandl, Ferdinand P. .

EUROPEAN JOURNAL OF PHARMACEUTICS AND BIOPHARMACEUTICS, 2015, 97 :438-453

[16] Copper-Catalyzed Diastereo- and Enantioselective Sequential Reactions of Propargylic Acetates with (E)-2,4-Pentadienylamine [J].

Hattori, Gaku ;

Miyake, Yoshihiro ;

Nishibayashi, Yoshiaki .

CHEMCATCHEM, 2010, 2 (02) :155-158

[17] Copper-Catalyzed Asymmetric Diyne Cyclization via [1,2]-Stevens-Type Rearrangement for the Synthesis of Chiral Chromeno[3,4-c]pyrroles [J].

Hong, Feng-Lin ;

Shi, Chong-Yang ;

Hong, Pan ;

Zhai, Tong-Yi ;

Zhu, Xin-Qi ;

Lu, Xin ;

Ye, Long-Wu .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (07)

[18] Transition Metal-Catalyzed Tandem Reactions of Ynamides for Divergent N-Heterocycle Synthesis [J].

Hong, Feng-Lin ;

Ye, Long-Wu .

ACCOUNTS OF CHEMICAL RESEARCH, 2020, 53 (09) :2003-2019

[19] Copper-Catalyzed Asymmetric Reaction of Alkenyl Diynes with Styrenes by Formal [3+2] Cycloaddition via Cu-Containing AllCarbon 1,3-Dipoles: Access to Chiral Pyrrole-Fused Bridged [2.2.1] Skeletons [J].

Hong, Feng-Lin ;

Chen, Yang-Bo ;

Ye, Si-Han ;

Zhu, Guang-Yu ;

Zhu, Xin-Qi ;

Lu, Xin ;

Liu, Rai-Shung ;

Ye, Long-Wu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (16) :7618-7626

[20] Generation of Donor/Donor Copper Carbenes through Copper-Catalyzed Diyne Cyclization: Enantioselective and Divergent Synthesis of Chiral Polycyclic Pyrroles [J].

Hong, Feng-Lin ;

Wang, Ze-Shu ;

Wei, Dong-Dong ;

Zhai, Tong-Yi ;

Deng, Guo-Cheng ;

Lu, Xin ;

Liu, Rai-Shung ;

Ye, Long-Wu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (42) :16961-16970

← 1 2 3 4 5 6 7 8 9 →