Synthesis of acridones through palladium-catalyzed carbonylative of 2-bromo-diarylamines

被引:7
作者
Song, Juan [1 ,2 ]
Ding, Keran [1 ,2 ]
Sun, Wei [3 ,4 ]
Wang, Songjiang [1 ,2 ]
Sun, Haisen [1 ,2 ]
Xiao, Kang [1 ,2 ]
Qian, Yan [1 ,2 ]
Liu, Chao [3 ]
机构
[1] Nanjing Univ Posts & Telecommun, Jiangsu Natl Synerget Innovat Ctr Adv Mat SICAM, Key Lab Organ Elect & Informat Displays, 9 Wenyuan Rd, Nanjing 210023, Jiangsu, Peoples R China
[2] Nanjing Univ Posts & Telecommun, Jiangsu Natl Synerget Innovat Ctr Adv Mat SICAM, Inst Adv Mat, Jiangsu Key Lab Biosensors, 9 Wenyuan Rd, Nanjing 210023, Jiangsu, Peoples R China
[3] Chinese Acad Sci, LICP, Suzhou Res Inst LICP, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Gansu, Peoples R China
[4] Univ Chinese Acad Sci, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
Palladium; Carbonylation; C-H activation; QUINACRIDONE; DERIVATIVES; ARYNES;
D O I
10.1016/j.tetlet.2018.06.004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile protocol for the synthesis of acridone derivatives has been developed through palladium-catalyzed carbonylation/C-H activation sequence from 2-bromo-diarylamines in moderate to excellent yields. The reactions occurred smoothly and allowed both electron-rich and electron-deficient substrates converted to the corresponding acridones. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2889 / 2892
页数:4
相关论文
共 35 条
[11]   AROMATIC NITRO-GROUP DISPLACEMENT-REACTIONS .1. NOVEL ROUTE TO SUBSTITUTED 10-PHENYLACRIDONES [J].
GORVIN, JH ;
WHALLEY, DP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (05) :1364-1370
[12]   Synthesis and evaluation of the antitumor activity of polyhalo acridone derivatives [J].
Huang, Chao ;
Yan, Sheng-Jiao ;
Zeng, Xiang-Hui ;
Sun, Bo ;
Lan, Min-Bo ;
Lin, Jun .
RSC ADVANCES, 2015, 5 (23) :17444-17450
[13]   Synthesis of 10-Methylacridin-9(10H)-ones through Cu-Catalyzed Intramolecular Oxidative C(sp2)-H Amination of 2-(Methylamino)benzophenones [J].
Huang, Jinbo ;
Wan, Congqing ;
Xu, Ming-Fang ;
Zhu, Qiang .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (10) :1876-1880
[14]  
Kazuhiro K., 2013, HELV CHIM ACTA, V96, P389
[15]   Discovery of dual function acridones as a new antimalarial chemotype [J].
Kelly, Jane X. ;
Smilkstein, Martin J. ;
Brun, Reto ;
Wittlin, Sergio ;
Cooper, Roland A. ;
Lane, Kristin D. ;
Janowsky, Aaron ;
Johnson, Robert A. ;
Dodean, Rozalia A. ;
Winter, Rolf ;
Hinrichs, David J. ;
Riscoe, Michael K. .
NATURE, 2009, 459 (7244) :270-273
[16]   A high performance green-sensitive organic photodiode comprising a bulk heterojunction of dimethyl-quinacridone and dicyanovinyl terthiophene [J].
Lee, Kwang-Hee ;
Leem, Dong-Seok ;
Sul, Soohwan ;
Park, Kyung-Bae ;
Lim, Seon-Jeong ;
Han, Hyouksoo ;
Kim, Kyu-Sik ;
Jin, Yong Wan ;
Lee, Sangyoon ;
Park, Soo Young .
JOURNAL OF MATERIALS CHEMISTRY C, 2013, 1 (15) :2666-2671
[17]   Highly Efficient Thermally Activated Delayed Fluorescence from an Excited-State Intramolecular Proton Transfer System [J].
Mamada, Masashi ;
Inada, Ko ;
Komino, Takeshi ;
Potscavage, William J., Jr. ;
Nakanotani, Hajime ;
Adachi, Chihaya .
ACS CENTRAL SCIENCE, 2017, 3 (07) :769-777
[18]   Quinoline, quinazoline and acridone alkaloids [J].
Michael, Joseph P. .
NATURAL PRODUCT REPORTS, 2008, 25 (01) :166-187
[19]   Design, synthesis, pharmacological evaluation, and docking study of new acridone-based 1,2,4-oxadiazoles as potential anticonvulsant agents [J].
Mohammadi-Khanaposhtani, Maryam ;
Shabani, Mohammad ;
Faizi, Mehrdad ;
Aghaei, Iraj ;
Jahani, Reza ;
Sharafi, Zainab ;
Zafarghandi, Narges Shamsaei ;
Mahdavi, Mohammad ;
Akbarzadeh, Tahmineh ;
Emami, Saeed ;
Shafiee, Abbas ;
Foroumadi, Alireza .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 112 :91-98
[20]   Dendritic incorporation of quinacridone: solubility, aggregation, electrochemistry, and solid-state luminescence [J].
Ortiz, A ;
Flora, WH ;
D'Ambruoso, GD ;
Armstrong, NR ;
McGrath, DV .
CHEMICAL COMMUNICATIONS, 2005, (04) :444-446