Synthesis of Original 2-Substituted 4-Arylquinazolines by Microwave-Irradiated Suzuki-Miyaura Cross-Coupling Reactions

被引:25
|
作者
Kabri, Youssef [1 ,2 ,3 ]
Gellis, Armand [1 ,2 ,3 ]
Vanelle, Patrice [1 ,2 ,3 ]
机构
[1] Univ Aix Marseille 1, Lab Chim Provence, Fac Pharm, LPCR, F-13385 Marseille 05, France
[2] Univ Aix Marseille 2, F-13385 Marseille 05, France
[3] Univ Aix Marseille 3, CNRS, UMR 6264, Lab Chim Provence, F-13385 Marseille 05, France
关键词
Boron; Microwave chemistry; Cross-coupling; Nitrogen heterocycles; DIHYDROFOLATE-REDUCTASE; ASSISTED SYNTHESIS; AQUEOUS-PHASE; ARYL BROMIDES; CATALYST-FREE; SOLVENT; DERIVATIVES; RESOLUTION; WATER;
D O I
10.1002/ejoc.200900421
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Original 2-substituted 4-arylquinazolines have been synthesized by using a microwave-assisted Suzuki-Miyaura cross-coupling approach. The optimization and generalization of the Suzuki-Miyaura cross-coupling reaction between 2-substituted 4-chloroquinazolines and various boronic acids are described herein. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
引用
收藏
页码:4059 / 4066
页数:8
相关论文
共 50 条
  • [1] Synthesis of biphenylamines via Suzuki-Miyaura cross-coupling reactions
    Maj, Anna M.
    Delaude, Lionel
    Demonceau, Albert
    Noels, Alfred F.
    TETRAHEDRON, 2007, 63 (12) : 2657 - 2663
  • [2] Suzuki-Miyaura cross-coupling reaction of aryl and heteroaryl pinacol boronates for the synthesis of 2-substituted pyrimidines
    Asano, Shigehiro
    Kamioka, Seiji
    Isobe, Yoshiaki
    TETRAHEDRON, 2012, 68 (01) : 272 - 279
  • [3] Azidosubstituted arylboronic acids: synthesis and Suzuki-Miyaura cross-coupling reactions
    Sviridov, SI
    Vasi'ev, AA
    Sergovskaya, NL
    Chirskaya, MV
    Shorshnev, SV
    TETRAHEDRON, 2006, 62 (11) : 2639 - 2647
  • [4] Chemoselective Synthesis of Arylpyridines through Suzuki-Miyaura Cross-Coupling Reactions
    Perdomo Rivera, Rodisnel
    Ehlers, Peter
    Ohlendorf, Lars
    Torres Rodriguez, Eugenio
    Villinger, Alexander
    Langer, Peter
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (08) : 990 - 1003
  • [5] Suzuki-miyaura cross-coupling reactions of potassium alkenyltrifluoroborates
    Molander, GA
    Bernardi, CR
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (24): : 8424 - 8429
  • [6] Synthesis of potassium heteroarylmethyltrifluoroborates and their use in Suzuki-Miyaura cross-coupling reactions
    Ryu, DaWeon
    Devulapally, Rammohan
    Molander, Gary A.
    Seapy, Dave G.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [7] Stereospecific and stereoselective Suzuki-Miyaura cross-coupling reactions
    Glasspoole, Ben W.
    Keske, Eric C.
    Crudden, Cathleen M.
    RSC Catalysis Series, 2015, 2015-January (21): : 521 - 550
  • [8] Orbital phase in Suzuki-Miyaura cross-coupling reactions
    Inagaki, Satoshi
    Ikeda, Hirotaka
    TETRAHEDRON LETTERS, 2014, 55 (14) : 2223 - 2225
  • [9] Suzuki-Miyaura Cross-Coupling Reactions of Unprotected Haloimidazoles
    Tan, Jiajing
    Chen, Yonggang
    Li, Hongmei
    Yasuda, Nobuyoshi
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (18): : 8871 - 8876
  • [10] Microwave assisted asymmetric Suzuki-Miyaura and Negishi cross-coupling reactions:: synthesis of chiral binaphthalenes
    Genov, Miroslav
    Almorin, Antonio
    Espinet, Pablo
    TETRAHEDRON-ASYMMETRY, 2007, 18 (05) : 625 - 627