AgNO3-catalyzed direct C-H arylation of quinolines by oxidative decarboxylation of aromatic carboxylic acids

被引:38
作者
Yuan, Jin-Wei [1 ]
Yang, Liang-Ru [1 ]
Mao, Pu [1 ]
Qu, Ling-Bo [1 ]
机构
[1] Henan Univ Technol, Academician Workstn Nat Med Chem Henan Prov, Sch Chem & Chem Engn, Zhengzhou 450001, Peoples R China
关键词
CROSS-COUPLING REACTIONS; RH(I)-CATALYZED DIRECT ARYLATION; RADICAL TANDEM CYCLIZATION; N-HETEROARYL HALIDES; SUZUKI-MIYAURA; ARYLBORONIC ACIDS; SUBSTITUTED QUINOLINES; BORONIC ACIDS; EFFICIENT SYNTHESIS; BOND ACTIVATION;
D O I
10.1039/c6qo00533k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient silver-catalyzed intermolecular decarboxylative arylation of quinolines has been developed using cheap aromatic carboxylic acids as arylating reagents under microwave irradiation. The reaction demonstrates a broad substrate scope and excellent functional group tolerance. This method provided an effective and easy way to synthesize arylated quinoline derivatives. The radical trapping experiments showed that this process involved the radical mechanism.
引用
收藏
页码:545 / 554
页数:10
相关论文
共 105 条
[1]   Electrochemical properties and electronic structures of conjugated polyquinolines and polyanthrazolines [J].
Agrawal, AK ;
Jenekhe, SA .
CHEMISTRY OF MATERIALS, 1996, 8 (02) :579-589
[2]   Reversal Agent and Linker Variants of Reversed Chloroquines: Activities against Plasmodium falciparum [J].
Andrews, Simeon ;
Burgess, Steven J. ;
Skaalrud, Deborah ;
Kelly, Jane Xu ;
Peyton, David H. .
JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (02) :916-919
[3]   A reassessment of the transition-metal free Suzuki-type coupling methodology [J].
Arvela, RK ;
Leadbeater, NE ;
Sangi, MS ;
Williams, VA ;
Granados, P ;
Singer, RD .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (01) :161-168
[4]   POTENTIAL ANTITUMOR AGENTS .57. 2-PHENYLQUINOLINE-8-CARBOXAMIDES AS MINIMAL DNA-INTERCALATING ANTITUMOR AGENTS WITH INVIVO SOLID TUMOR-ACTIVITY [J].
ATWELL, GJ ;
BAGULEY, BC ;
DENNY, WA .
JOURNAL OF MEDICINAL CHEMISTRY, 1989, 32 (02) :396-401
[5]   The biology and chemistry of the zoanthamine alkaloids [J].
Behenna, Douglas C. ;
Stockdill, Jennifer L. ;
Stoltz, Brian M. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (13) :2365-2386
[6]   Regioselective Metal-Free Cross-Coupling of Quinoline N-Oxides with Boronic Acids [J].
Bering, Luis ;
Antonchick, Andrey P. .
ORGANIC LETTERS, 2015, 17 (12) :3134-3137
[7]   Rh(I)-Catalyzed Direct Arylation of Pyridines and Quinolines [J].
Berman, Ashley M. ;
Lewis, Jared C. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (45) :14926-+
[8]   Rh(I)-Catalyzed Direct Arylation of Azines [J].
Berman, Ashley M. ;
Bergman, Robert G. ;
Ellman, Jonathan A. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (22) :7863-7868
[9]   Anti-leishmanial evaluation of C2-aryl quinolines: Mechanistic insight on bioenergetics and sterol biosynthetic pathway of Leishmania braziliensis [J].
Bompart, Daznia ;
Nunez-Duran, Jorge ;
Rodriguez, Daniel ;
Kouznetsov, Vladimir V. ;
Melendez Gomez, Carlos M. ;
Sojo, Felipe ;
Arvelo, Francisco ;
Visbal, Gonzalo ;
Alvarez, Alvaro ;
Serrano-Martin, Xenon ;
Garcia-Marchan, Yael .
BIOORGANIC & MEDICINAL CHEMISTRY, 2013, 21 (14) :4426-4431
[10]   Decarboxylative functionalization of cinnamic acids [J].
Borah, Arun Jyoti ;
Yan, Guobing .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (30) :8094-8115