Facile Synthesis of π-Conjugated Quinazoline-Substituted Ethenes from 2-Ethynylanilines and Benzonitriles under Transition-Metal-Free Conditions

被引:14
|
作者
Wang, Xu [2 ]
Li, Jiawei [2 ]
Huang, Yubing [2 ]
Zhu, Jiayi [2 ]
Hu, Rongrong [1 ]
Wu, Wanqing [1 ,2 ]
Jiang, Huanfeng [2 ]
机构
[1] South China Univ Technol, State Key Lab Luminescent Mat & Devices, Guangzhou 510640, Guangdong, Peoples R China
[2] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 17期
基金
中国国家自然科学基金;
关键词
AGGREGATION-INDUCED EMISSION; CROSS-COUPLING REACTIONS; ONE-POT SYNTHESIS; C-H ARYLATION; ROOM-TEMPERATURE; DOMINO REACTION; BENZOIC-ACIDS; DIRECT ACCESS; ACTIVATION; ALKYNYLATION;
D O I
10.1021/acs.joc.8b01494
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new transition-metal-free version for the synthesis of ir-conjugated quinazoline-substituted ethene derivatives from readily available starting materials has been developed. Quinazoline-substituted ethenes were obtained in moderate to high yields with completely Z-selectivity, and the resulting quinazoline-substituted ethenes show typical aggregation-induced emission (AIE) properties.
引用
收藏
页码:10453 / 10464
页数:12
相关论文
共 50 条
  • [41] NaHSO3-Mediated Direct Synthesis of Sulfinic Esters from Sulfonyl Hydrazides under Transition-Metal-Free Conditions
    Zhang, Guofu
    Fan, Qiankun
    Wang, Huimin
    Zhao, Yiyong
    Ding, Chengrong
    ADVANCED SYNTHESIS & CATALYSIS, 2021, 363 (03) : 833 - 837
  • [42] Transition-Metal-Free Synthesis of Conjugated Polymers from Bis-Grignard Reagents by Using TEMPO as Oxidant
    Maji, Modhu Sudan
    Pfeifer, Thorben
    Studer, Armido
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (20) : 5872 - 5875
  • [43] Transition-metal-free synthesis of quinolines from 2-nitrobenzyl alcohol in water
    Zhu, Meijuan
    Wang, Chao
    Tang, Weijun
    Xiao, Jianliang
    TETRAHEDRON LETTERS, 2015, 56 (48) : 6758 - 6761
  • [44] Heteroarylation of Sulfenate Ions In Situ Generated from β-Sulfinyl Esters under Transition-Metal-Free Conditions
    Pilathottathil, Fathima
    Unnikrishnan, Sreelakshmi
    Kaliyamoorthy, Alagiri
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (21): : 14980 - 14990
  • [45] Base-promoted synthesis of coumarins from salicylaldehydes and aryl-substituted 1,1-dibromo-1-alkenes under transition-metal-free conditions
    Liu, Jianming
    Zhang, Xin
    Shi, Lijun
    Liu, Muwen
    Yue, Yuanyuan
    Li, Fuwei
    Zhuo, Kelei
    CHEMICAL COMMUNICATIONS, 2014, 50 (69) : 9887 - 9890
  • [46] Sodium persulfate-promoted site-selective synthesis of mononitroarylamines under transition-metal-free conditions
    Xie, De-Xun
    Yu, Hui-Juan
    Liu, Hui
    Xue, Wei-Cai
    Qin, Yuan-Shou
    Shao, Guang
    TETRAHEDRON, 2019, 75 (09) : 1157 - 1165
  • [47] Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions
    Zhang, Xitao
    Feng, Xiujuan
    Zhang, Haixia
    Yamamoto, Yoshinori
    Bao, Ming
    GREEN CHEMISTRY, 2019, 21 (20) : 5565 - 5570
  • [48] Synthesis of Ketones by C-H Functionalization of Aldehydes with Boronic Acids under Transition-Metal-Free Conditions
    Roscales, Silvia
    Csaky, Aurelio G.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2021, 60 (16) : 8728 - 8732
  • [49] Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions
    Zhang, Xitao
    Feng, Xiujuan
    Zhou, Chuancheng
    Yu, Xiaoqiang
    Yamamoto, Yoshinori
    Bao, Ming
    ORGANIC LETTERS, 2018, 20 (22) : 7095 - 7099
  • [50] Synthesis of Fluorinated Heteroaromatics through Formal Substitution of a Nitro Group by Fluorine under Transition-Metal-Free Conditions
    Guo, Ran-Ning
    Cai, Xian-Feng
    Shi, Lei
    Chen, Zhang-Pei
    Zhou, Yong-Gui
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (27) : 8343 - 8346