Organocatalytic cascade 1,6-conjugate addition/annulation/tautomerization of functionalized para-quinone methides: Access to chiral 2-amino-4-aryl-4H-chromenes

被引:31
作者
Duan, Cong [1 ]
Ye, Ling [2 ]
Xu, Wenqin [1 ]
Li, Xinying [1 ]
Chen, Feng [1 ]
Zhao, Zhigang [1 ]
Li, Xuefeng [1 ]
机构
[1] Southwest Minzu Univ, Coll Chem & Environm Protect Engn, Chengdu 610041, Sichuan, Peoples R China
[2] Southwest Jiaotong Univ, Fac Geosci & Environm Engn, Chengdu 610031, Sichuan, Peoples R China
基金
中国国家自然科学基金;
关键词
pars-Quinone methides; 2-Amino-4-aryl-4H-chromene; Domino reaction; 1,6-Conjugated addition; Enantioselective; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; APOPTOSIS INDUCERS; CONJUGATE ADDITION; ACID-ESTERS; IN-SITU; DERIVATIVES; DISCOVERY; SERIES; 2-AMINO-4H-CHROMENES;
D O I
10.1016/j.cclet.2017.11.044
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel organocatalytic cascade process initiated by 1,6-conjugated addition has been successfully developed. A range of pharmaceutically active 2-amino-4-aryl-4H-chromenes were readily obtained in high yields (88%-99%) and excellent enantiopurities (86%-99% ee). The functionalized para-Quinone methides (p-OMs) could be facilely obtained. (C) 2018 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:1273 / 1276
页数:4
相关论文
共 48 条
[1]   Quinine-catalyzed highly enantioselective cycloannulation of o-quinone methides with malononitrile [J].
Adili, Alafate ;
Tao, Zhong-Lin ;
Chen, Dian-Feng ;
Han, Zhi-Yong .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (08) :2247-2250
[2]  
Cai S.X., 2011, Patent No. [7,968,595 B2, 7968595]
[3]   Small molecule vascular disrupting agents: Potential new drugs for cancer treatment [J].
Cai, Sui X. .
RECENT PATENTS ON ANTI-CANCER DRUG DISCOVERY, 2007, 2 (01) :79-101
[4]   Discovery of 4-Aryl-4H-Chromenes as Potent Apoptosis Inducers Using a Cell- and Caspase-Based Anti-Cancer Screening Apoptosis Program (ASAP): SAR Studies and the Identification of Novel Vascular Disrupting Agents [J].
Cai, Sui Xiong ;
Drewe, John ;
Kemnitzer, William .
ANTI-CANCER AGENTS IN MEDICINAL CHEMISTRY, 2009, 9 (04) :437-456
[5]   The Emergence of Quinone Methides in Asymmetric Organocatalysis [J].
Caruana, Lorenzo ;
Fochi, Mariafrancesca ;
Bernardi, Luca .
MOLECULES, 2015, 20 (07) :11733-11764
[6]   Catalytic Asymmetric Addition of Meldrum's Acid, Malononitrile, and 1,3-Dicarbonyls to ortho-Quinone Methides Generated In Situ Under Basic Conditions [J].
Caruana, Lorenzo ;
Mondatori, Martina ;
Corti, Vasco ;
Morales, Sara ;
Mazzanti, Andrea ;
Fochi, Mariafrancesca ;
Bernardi, Luca .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (16) :6037-6041
[7]   A New Organocatalytic Concept for Asymmetric α-Alkylation of Aldehydes [J].
Caruana, Lorenzo ;
Kniep, Florian ;
Johansen, Tore Kiilerich ;
Poulsen, Pernille H. ;
Jorgensen, Karl Anker .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (45) :15929-15932
[8]   Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective Construction of Remote Stereogenic Centers [J].
Chauhan, Pankaj ;
Kaya, Ugur ;
Enders, Dieter .
ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (06) :888-912
[9]   Enantioselective One-Pot Synthesis of 2-Amino-4-(indol-3-yl)-4H-Chromenes [J].
Chen, Weiliang ;
Cai, Yunfei ;
Fu, Xuan ;
Liu, Xiaohua ;
Lin, Lili ;
Feng, Xiaoming .
ORGANIC LETTERS, 2011, 13 (18) :4910-4913
[10]   Asymmetric Catalytic 1,6-Conjugate Addition/Aromatization of para-Quinone Methides: Enantioselective Introduction of Functionalized Diarylmethine Stereogenic Centers [J].
Chu, Wen-Dao ;
Zhang, Le-Fen ;
Bao, Xu ;
Zhao, Xian-He ;
Zeng, Chao ;
Du, Ji-Yuan ;
Zhang, Guo-Biao ;
Wang, Fang-Xin ;
Ma, Xiao-Yan ;
Fan, Chun-An .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9229-9233