Methylation of imidazopyrazine, imidazoquinoxaline, and pyrazoloquinoxaline through Suzuki-Miyaura cross coupling

被引:3
作者
Karroum, Nour Bou [1 ,2 ]
Patinote, Cindy [1 ,3 ]
Deleuze-Masquefa, Carine [1 ]
Moarbess, Georges [2 ]
Diab-Assaf, Mona [2 ]
Cuq, Pierre [1 ]
Kassab, Issam [2 ]
Bonnet, Pierre-Antoine [1 ]
机构
[1] Univ Montpellier, IBMM, CNRS, ENSCM, Montpellier, France
[2] Lebanese Univ, EDST, Tumorigenese & Pharmacol Antitumorale, BP 90656, Fanar Jdeideh, Lebanon
[3] Soc Accelerat Transfert Technol SATT AxLR, CSU, 950 Rue St Priest, F-34090 Montpellier, France
关键词
imidazo[1,2-a]pyrazine; imidazo[1,2-a]quinoxaline; pyrazolo[1,5-a]quinoxaline; methylation; Suzuki-Miyaura cross coupling; IN-VITRO; DERIVATIVES; ACIDS; INHIBITORS; ARYL; HALIDES;
D O I
10.1007/s10593-018-2252-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Suzuki-Miyaura cross coupling is a versatile and powerful reaction for carbon-carbon bond formation which nevertheless requires optimization of conditions. While the coupling of arylboron derivatives with aryl or alkenyl halides has been widely explored, alkylation has attracted less attention. We describe herein the methylation of bromo derivatives of imidazopyrazine, imidazoquinoxaline, and pyrazoloquinoxaline having biologically interesting structures. As the challenging Suzuki-Miyaura reaction is highly substratedependent, the choices of the base, solvent, and additive are also discussed.
引用
收藏
页码:183 / 187
页数:5
相关论文
共 50 条
  • [41] Chemoselective Suzuki-Miyaura Coupling of Bromophenyl-Substituted Bromoallenes with Arylboronic Acids
    Du, Xin
    Liu, Xuesong
    Xu, Liang
    Jiang, Wenfeng
    Bao, Ming
    He, Ren
    SYNLETT, 2012, (10) : 1505 - 1510
  • [42] Suzuki-Miyaura Cross-Coupling under Solvent-Free Conditions
    Asachenko, Andrey F.
    Sorochkina, Kristina R.
    Dzhevakov, Pavel B.
    Topchiy, Maxim A.
    Nechaev, Mikhail S.
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3553 - 3557
  • [43] Cobalt pincer complex catalyzed Suzuki-Miyaura cross coupling - A green approach
    Kumar, Lolakshi Mahesh
    Bhat, Badekai Ramachandra
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2017, 827 : 41 - 48
  • [44] Postsynthetic Modification of Peptoids via the Suzuki-Miyaura Cross-Coupling Reaction
    Nam, Ho Yeon
    Seo, Jiwon
    BIOPOLYMERS, 2016, 106 (01) : 82 - 88
  • [45] Suzuki-Miyaura Cross-Coupling in Acylation Reactions, Scope and Recent Developments
    Blangetti, Marco
    Rosso, Helena
    Prandi, Cristina
    Deagostino, Annamaria
    Venturello, Paolo
    MOLECULES, 2013, 18 (01) : 1188 - 1213
  • [46] Stereospecific Suzuki-Miyaura Coupling of Chiral α-(Acylamino)benzylboronic Esters with Inversion of Configuration
    Ohmura, Toshimichi
    Awano, Tomotsugu
    Suginome, Michinori
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (38) : 13191 - 13193
  • [47] Carbonylative and direct Suzuki-Miyaura cross-coupling reactions with 1-iodo-cyclohexene
    Petz, Andrea
    Peczely, Gabor
    Pinter, Zoltan
    Kollar, Laszlo
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 255 (1-2) : 97 - 102
  • [48] Peptide stapling by late-stage Suzuki-Miyaura cross-coupling
    Gruss, Hendrik
    Feiner, Rebecca C.
    Mseya, Ridhiwan
    Schroeder, David C.
    Jewginski, Michat
    Mueller, Kristian M.
    Latajka, Rafat
    Marion, Antoine
    Sewald, Norbert
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 1 - 12
  • [49] Expedient synthesis of 4-O-methylhonokiol via Suzuki-Miyaura cross-coupling
    Kwak, Jae-Hwan
    Cho, Young Ae
    Jang, Jae-Yong
    Seo, Seung-Yong
    Lee, Heesoon
    Hong, Jin Tae
    Han, Sang-Bae
    Lee, Kiho
    Kwak, Young-Shin
    Jung, Jae-Kyung
    TETRAHEDRON, 2011, 67 (48) : 9401 - 9404
  • [50] Sterically demanding aryl-alkyl Suzuki-Miyaura coupling
    Li, Chengxi
    Xiao, Guolan
    Zhao, Qing
    Liu, Huimin
    Wang, Tao
    Tang, Wenjun
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (03): : 225 - 229