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
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
收藏
页码:1501 / 1508
页数:8
相关论文
共 83 条
[71]   Synthesis of functionalized 3-isochromanones via metal-free intramolecular alkoxylation-initiated cascade cyclization [J].
Zhang, Ying-Qi ;
Zhu, Xin-Qi ;
Xu, Yin ;
Bu, Hao-Zhen ;
Wang, Jia-Le ;
Zhai, Tong-Yi ;
Zhou, Jin-Mei ;
Ye, Long-Wu .
GREEN CHEMISTRY, 2019, 21 (11) :3023-3028
[72]   Gold-Catalyzed Formal Dehydro-Diels-Alder Reactions of Ene-Ynamide Derivatives Bearing Terminal Alkyne Chains: Scope and Mechanistic Studies [J].
Zhao, Qing ;
Leon Rayo, David Fabian ;
Campeau, Dominic ;
Daenen, Martin ;
Gagosz, Fabien .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (41) :13603-13607
[73]  
Zhao Y., 2021, CHINESE J ORG CHEM, V41, P85
[74]   1,4-Functionalization of 3-En-1-ynes with Alcohols via Zinc-Catalyzed Regioselective N-Oxide Oxidation [J].
Zheng, Renhua ;
Guo, Haichang ;
Yang, Mingyang ;
Liu, Mengqi ;
Ye, Longwu .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (06) :1672-1680
[75]   Reversal of Regioselectivity in Ynamide Chemistry [J].
Zhou, Bo ;
Tan, Tong-De ;
Zhu, Xin-Qi ;
Shang, Mingzhou ;
Ye, Long-Wu .
ACS CATALYSIS, 2019, 9 (07) :6393-6406
[76]   Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement [J].
Zhou, Bo ;
Zhang, Ying-Qi ;
Zhang, Kairui ;
Yang, Ming-Yang ;
Chen, Yang-Bo ;
Li, You ;
Peng, Qian ;
Zhu, Shou-Fei ;
Zhou, Qi-Lin ;
Ye, Long-Wu .
NATURE COMMUNICATIONS, 2019, 10 (1)
[77]   Yttrium-Catalyzed Intramolecular Hydroalkoxylation/Claisen Rearrangement Sequence: Efficient Synthesis of Medium-Sized Lactams [J].
Zhou, Bo ;
Li, Long ;
Zhu, Xin-Qi ;
Yan, Juan-Zhu ;
Guo, Yi-Lin ;
Ye, Long-Wu .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (14) :4015-4019
[78]   Recent Advances in the Ring-Forming Reactions of Ynamides [J].
Zhou, Xinyue ;
Liang, Zongxian ;
Wang, Xiao-Na .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (04) :1288-1318
[79]   Catalytic hydrative cyclization of aldehyde-ynamides with water for synthesis of medium-sized lactams [J].
Zhu, Bo-Han ;
Zheng, Yan-Xin ;
Kang, Wei ;
Deng, Chao ;
Zhou, Jin-Mei ;
Ye, Long-Wu .
SCIENCE CHINA-CHEMISTRY, 2021, 64 (11) :1985-1989
[80]   NaBArF4-Catalyzed Oxidative Cyclization of 1,5-and 1,6-Diynes: Efficient and Divergent Synthesis of Functionalized γ- and δ-Lactams [J].
Zhu, Bo-Han ;
Wang, Cai-Ming ;
Su, Hong-Yu ;
Ye, Long-Wu .
CHINESE JOURNAL OF CHEMISTRY, 2019, 37 (01) :58-62