Synthesis of spiroindolenine-bearing chroman scaffolds based on a cyclization reaction of para-Quinone methides

被引：4
作者：
Qin, Hongmei [1 ]
Xie, Qimei [2 ]
He, Long [1 ,2 ]
机构：
[1] Guiyang Univ, Coll Chem & Mat Engn, Guiyang 550005, Peoples R China
[2] China West Normal Univ, Coll Chem & Chem Engn, Nanchong 637002, Peoples R China
来源：
NEW JOURNAL OF CHEMISTRY | 2022年 / 46卷 / 21期
基金：
中国国家自然科学基金;
关键词：
D O I：
10.1039/d2nj00936f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An efficient diastereoselective cyclization reaction of orthohydroxyphenyl-substituted para-quinone methides with alpha,beta-unsaturated imines generated in situ from aryl sulfonyl indoles was developed, and afforded spiroindolenine-bearing chroman scaffolds in good to excellent yields (up to 98%) and diastereoselectivities (up to >19 :1 d.r.). This protocol provided an efficient method for constructing spirocyclic compounds incorporating two pharmacophores, namely chroman and spiroindoline.
引用
收藏
页码：9985 / 9988
页数：4
相关论文
共 44 条
[11]   Recent Advances in the Catalytic Enantioselective Reactions of para-Quinone Methides [J].
Li, Wenjun ;
Xu, Xianhong ;
Zhang, Pengfei ;
Li, Pengfei .
CHEMISTRY-AN ASIAN JOURNAL, 2018, 13 (17) :2350-2359
[12]   Catalyst-Enabled Scaffold Diversity: Highly Chemo-and Stereoselective Synthesis of Tricyclic Ketals and Triarylmethanes [J].
Liao, Jia-Yu ;
Ni, Qijian ;
Zhao, Yu .
ORGANIC LETTERS, 2017, 19 (15) :4074-4077
[13]   para-Quinone Methides as Acceptors in 1,6-Nucleophilic Conjugate Addition Reactions for the Synthesis of Structurally Diverse Molecules [J].
Lima, Carolina G. S. ;
Pauli, Fernanda P. ;
Costa, Dora C. S. ;
de Souza, Acacio S. ;
Forezi, Luana S. M. ;
Ferreira, Vitor F. ;
da Silva, Fernando de Silva .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 2020 (18) :2650-2692
[14]   Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening [J].
Lin, Li-Gen ;
Xie, Hua ;
Li, Hong-Lin ;
Tong, Lin-Jiang ;
Tang, Chun-Ping ;
Ke, Chang-Qiang ;
Liu, Qun-Fang ;
Lin, Li-Ping ;
Geng, Mei-Yu ;
Jiang, Hualiang ;
Zhao, Wei-Min ;
Ding, Jian ;
Ye, Yang .
JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) :4419-4429
[15]   1,6-Conjugated addition-mediated [4+1] annulation: an approach to 2,3-dihydrobenzofurans [J].
Liu, Lina ;
Yuan, Zhenbo ;
Pan, Rui ;
Zeng, Yuye ;
Lin, Aijun ;
Yao, Hequan ;
Huang, Yue .
ORGANIC CHEMISTRY FRONTIERS, 2018, 5 (04) :623-628
[16]   Ag/Bronsted Acid Co-Catalyzed Spiroketalization of β-Alkynyl Ketones toward Spiro[chromane-2,1'-isochromene] Derivatives [J].
Liu, Shuai ;
Lan, Xin-Chan ;
Chen, Ke ;
Hao, Wen-Juan ;
Li, Guigen ;
Tu, Shu-Jiang ;
Jiang, Bo .
ORGANIC LETTERS, 2017, 19 (14) :3831-3834
[17]   Melosuavines A-H, Cytotoxic Bisindole Alkaloid Derivatives from Melodinus suaveolens [J].
Liu, Ya-Ping ;
Zhao, Yun-Li ;
Feng, Tao ;
Cheng, Gui-Guang ;
Zhang, Bao-Hong ;
Li, Yan ;
Cai, Xiang-Hai ;
Luo, Xiao-Dong .
JOURNAL OF NATURAL PRODUCTS, 2013, 76 (12) :2322-2329
[18]   Palladium-Catalyzed Asymmetric Cycloadditions of Vinylcyclopropanes and in Situ Formed Unsaturated lmines: Construction of Structurally and Optically Enriched Spiroindolenines [J].
Liu, Ze-Shui ;
Li, Wen-Ke ;
Kang, Tai-Ran ;
He, Long ;
Liu, Quan-Zhong .
ORGANIC LETTERS, 2015, 17 (01) :150-153
[19]   Preparation and antiplasmodial activity of 3',4'-dihydro-1'H-spiro(indoline-3,2'-quinolin)-2-ones [J].
Mathebula, Bakolise ;
Butsi, Kamogelo Rosinah ;
van Zyl, Robyn Lynne ;
van Vuuren, Natasha Colleen Jansen ;
Hoppe, Heinrich Carl ;
Michael, Joseph Philip ;
de Koning, Charles Bernard ;
Rousseau, Amanda Louise .
CHEMICAL BIOLOGY & DRUG DESIGN, 2019, 94 (04) :1849-1858
[20]   [4+2] Cyclization of para-Quinone Methide Derivatives with Alkynes [J].
Mei, Guang-Jian ;
Xu, Shao-Li ;
Zheng, Wen-Qin ;
Bian, Chen-Yu ;
Shi, Feng .
JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (03) :1414-1421
12345