Citation: M. Nibin Joy, Bhaskaran Savitha, Ayyiliyath M. Sajith, Yadav D. Bodke, Talavara Venkatesh, K. K. Abdul Khader, M. Syed Ali Padusha, A. Muralidharan. A facile access for the synthesis of some C-2 substituted imidazopyrazines by utilizing the palladium catalyzed Suzuki cross-coupling reaction under microwave irradiation[J]. Chinese Chemical Letters, ;2016, 27(01): 31-36. doi: 10.1016/j.cclet.2015.08.015 shu

A facile access for the synthesis of some C-2 substituted imidazopyrazines by utilizing the palladium catalyzed Suzuki cross-coupling reaction under microwave irradiation

  • Corresponding author: Ayyiliyath M. Sajith,  Yadav D. Bodke, 
  • Received Date: 25 June 2015
    Available Online: 3 August 2015

  • A rapid, efficient, and facile synthesis of an assortment of C-2 substituted imidazopyrazines has been achieved by utilizing the palladium catalyzed Suzuki cross-coupling of 2-bromo-1H-imidazo[4,5-b]pyrazine with various boronic acids under microwave irradiation. The utilization of(A-taphos)2PdCl2 as a catalyst in combination with CsF as base and DME-H2O(4:1) as the solvent system at 100℃ procured the diaryls in acceptable to excellent yields. Prominent features of this developed methodology include short reaction times, fewer side products, and exceptional tolerance to a wide variety of functional groups.
  • 加载中
    1. [1]

      [1](a) P.C. Shyma, B. Kalluraya, S.K. Peethambar, S. Telkar, T. Arulmoli, Synthesis, characterization and molecular docking studies of some new 1,3,4-oxadiazolines bearing 6-methylpyridine moiety for antimicrobial property, Eur. J. Med. Chem. 68(2013) 394-404;(b) A.M. Vijesh, A.M. Isloor, S.K. Peethambar, et al., Hantzsch reaction:synthesis and characterization of some new 1,4-dihydropyridine derivatives as potent antimicrobial and antioxidant agents, Eur. J. Med. Chem. 46(2011) 5591-5597.

    2. [2]

      [2](a) A.F. Littke, G.C. Fu, Palladium catalyzed coupling reactions of aryl chlorides, Angew. Chem. Int. Ed. 41(2002) 4176-4211;(b) S. Kotha, K. Lahiri, D. Kashinath, Recent applications of the Suzuki-Miyaura cross-coupling reaction in organic synthesis, Tetrahedron 58(2002) 9633-9695;(c) F. Alonso, I.P. Beletskaya, M. Yus, Non-conventional methodologies for transition metal catalyzed carbon-carbon coupling:a critical overview. Part 2:The Suzuki reaction, Tetrahedron 64(2008) 3047-3101;(d) R. Rossi, F. Bellina, M. Lessi, Highly selective palladium-catalyzed Suzuki-Miyaura monocoupling reactions of ethene and arene derivatives bearing two or more electrophilic sites, Tetrahedron 67(2011) 6969-7025.

    3. [3]

      [3] M.O.C. Galcera, L. Poitout, C. Moinet, et al., Synthesis of substituted imidazopyrazines as ligands for the human somatostatin receptor subtype 5, Bioorg. Med. Chem. Lett. 11(2001) 741-745.

    4. [4]

      [4] T. Hirano, T. Sekiguchi, D. Hashizume, et al., Colorimetric and fluorometric sensing of the Lewis acidity of a metal ion by metal-ion complexation of imidazo[1,2-a]pyrazin-3(7H)-ones, Tetrahedron 66(2010) 3842-3848.

    5. [5]

      [5](a) C.O. Kappe, D. Dallinger, Controlled microwave heating in modern organic synthesis, Mol. Divers. 13(2009) 71-193;(b) E.N. Koini, N. Avlonitis, E.S. Martins-Durate, et al., Divergent synthesis of 2,6-diaryl-substituted 5,7,8-trimethyl-1,4-benzoxazines via microwave-promoted palladium-catalyzed Suzuki-Miyaura cross coupling and biological evaluation, Tetrahedron 68(2012) 10302-10309;(c) C.O. Kappe, Controlled microwave heating in modern organic synthesis, Angew. Chem. Int. Ed. 43(2004) 6250-6284.

    6. [6]

      [6](a) A.M. Sajith, K.K. Abdul Khader, N. Joshi, et al., Design, synthesis and structureactivity relationship(SAR) studies of imidazo[4,5-b] pyridine derived purine isosteres and their potential as cytotoxic agents, Eur. J. Med. Chem. 89(2015) 21-31;(b) A. Chandrashekar, B. Eshwarappa, Y.D. Bodke, et al., Synthesis and evaluation of antioxidant properties of novel 1,2,4-triazole-based Schiff base heterocycles, Arch. Pharm. Chem. Life Sci. 346(2013) 922-930;(c) R. Kenchappa, Y.D. Bodke, S.K. Peethambar, S. Telkar, V.K. Bhovi, Synthesis of b-amino carbonyl derivatives of coumarin and benzofuran and evaluation of their biological activity, Med. Chem. Res. 22(2013) 4787-4797.

    7. [7]

      [7](a) K.K. Abdul Khader, A.M. Sajith, M.S.A. Padusha, H.P. Nagaswarupa, A. Muralidharan, Cycloalkenyl nonaflates as electrophilic cross-coupling substrates for palladium catalyzed C-N bond forming reactions with enolizable heterocycles under microwave enhanced conditions, New J. Chem. 38(2014) 1294-1305;(b) K.K. Abdul Khader, A.M. Sajith, M.S.A. Padusha, H.P. Nagaswarupa, A. Muralidharan, Regioselective synthesis of C-2 substituted imidazo[4,5-b]pyridines utilizing palladium catalysed C-N bond forming reactions with enolizable heterocycles, Tetrahedron Lett. 55(2014) 1778-1783;(c) M.N. Joy, Y.D. Bodke, K.K. Abdul Khader, A.M. Sajith, A rapid approach for the copper, amine and ligand-free Sonogashira coupling of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation, Tetrahedron Lett. 55(2014) 2355-2361;(d) A.M. Sajith, A. Muralidharan, Exploration of copper and amine-free Sonogashira cross coupling reactions of 2-halo-3-alkyl imidazo[4,5-b]pyridines using tetrabutyl ammonium acetate as an activator under microwave enhanced conditions, Tetrahedron Lett. 53(2012) 5206-5210;(e) M.N. Joy, Y.D. Bodke, K.K. Abdul Khader, et al., A rapid and modified approach for C-7 amination and amidation of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation, RSC Adv. 4(2014) 19766-19777.

    8. [8]

      [8](a) O.O. Navarro, H. Kaur, P. Mahjoor, S.P. Nolan, Cross-coupling and dehalogenation reactions catalyzed by(N-heterocyclic carbene)Pd(allyl)Cl complexes, J. Org. Chem. 69(2004) 3173-3180;(b) J. Moon, S. Lee, Palladium catalyzed-dehalogenation of aryl chlorides and bromides using phosphate ligands, J. Organomet. Chem. 694(2004) 473-477.

    9. [9]

      [9](a) A.S. Guram, X. Wang, E.E. Bunel, et al., New catalysts for Suzuki-miyaura coupling reactions of heteroatom-substituted heteroaryl chlorides, J. Org. Chem. 72(2007) 5104-5112;(b) V.F. Slagt, A.H.V. Vries, J.G. Vries, R.M. Kellogg, Practical aspects of carbon-carbon cross-coupling reactions using heteroarenes, Org. Proc. Res. Dev. 14(2010) 30-47;(c) A.M. Sajith, A. Muralidharan, Microwave enhanced Suzuki coupling:a diversity-oriented approach to the synthesis of highly functionalised 3-substituted-2-aryl/heteroaryl imidazo[4,5-b]pyridines, Tetrahedron Lett. 53(2012) 1036-1041.

  • 加载中
    1. [1]

      Qiang CaoXue-Feng ChengJia WangChang ZhouLiu-Jun YangGuan WangDong-Yun ChenJing-Hui HeJian-Mei Lu . Graphene from microwave-initiated upcycling of waste polyethylene for electrocatalytic reduction of chloramphenicol. Chinese Chemical Letters, 2024, 35(4): 108759-. doi: 10.1016/j.cclet.2023.108759

    2. [2]

      Qinwen ZhengXin LiuLintao TianYi ZhouLibing LiaoGuocheng Lv . Mechanism of Fenton catalytic degradation of Rhodamine B induced by microwave and Fe3O4. Chinese Chemical Letters, 2025, 36(4): 109771-. doi: 10.1016/j.cclet.2024.109771

    3. [3]

      Yuexiang LiuXiangqiao YangTong LinGuantian YangXiaoyong XuBubing ZengZhong LiWeiping ZhuXuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747

    4. [4]

      Xinlong HanHuiying ZengChao-Jun Li . Trifluoromethylative homo-coupling of carbonyl compounds. Chinese Chemical Letters, 2025, 36(1): 109817-. doi: 10.1016/j.cclet.2024.109817

    5. [5]

      Qijun Tang Wenguang Tu Yong Zhou Zhigang Zou . High efficiency and selectivity catalyst for photocatalytic oxidative coupling of methane. Chinese Journal of Structural Chemistry, 2023, 42(12): 100170-100170. doi: 10.1016/j.cjsc.2023.100170

    6. [6]

      Kongchuan WuDandan LuJianbin LinTing-Bin WenWei HaoKai TanHui-Jun Zhang . Elucidating ligand effects in rhodium(Ⅲ)-catalyzed arene–alkene coupling reactions. Chinese Chemical Letters, 2024, 35(5): 108906-. doi: 10.1016/j.cclet.2023.108906

    7. [7]

      Shengkai LiYuqin ZouChen ChenShuangyin WangZhao-Qing Liu . Defect engineered electrocatalysts for C–N coupling reactions toward urea synthesis. Chinese Chemical Letters, 2024, 35(8): 109147-. doi: 10.1016/j.cclet.2023.109147

    8. [8]

      Xin Huang Yi Zhao Wanzhen Liang . Vibronic coupling effect on intersystem crossing rates of TADF emitters. Chinese Journal of Structural Chemistry, 2024, 43(6): 100278-100278. doi: 10.1016/j.cjsc.2024.100278

    9. [9]

      Jian Ji Jie Yan Honggen Peng . Modulation of dinuclear site by orbital coupling to boost catalytic performance. Chinese Journal of Structural Chemistry, 2024, 43(8): 100360-100360. doi: 10.1016/j.cjsc.2024.100360

    10. [10]

      Yuehai ZhiChen GuHuachao JiKang ChenWenqi GaoJianmei ChenDafeng Yan . The advanced development of innovative photocatalytic coupling strategies for hydrogen production. Chinese Chemical Letters, 2025, 36(1): 110234-. doi: 10.1016/j.cclet.2024.110234

    11. [11]

      Jing GuoZhi-Guo LuRui-Chen ZhaoBao-Ku LiXin Zhang . Nucleic acid therapy for metabolic-related diseases. Chinese Chemical Letters, 2025, 36(3): 109875-. doi: 10.1016/j.cclet.2024.109875

    12. [12]

      Baokang GengXiang ChuLi LiuLingling ZhangShuaishuai ZhangXiao WangShuyan SongHongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924

    13. [13]

      Lang GaoCen ZhouRui WangFeng LanBohang AnXiaozhou HuangXiao Zhang . Unveiling inverse vulcanized polymers as metal-free, visible-light-driven photocatalysts for cross-coupling reactions. Chinese Chemical Letters, 2024, 35(4): 108832-. doi: 10.1016/j.cclet.2023.108832

    14. [14]

      Mengli Xu Zhenmin Xu Zhenfeng Bian . Achieving Ullmann coupling reaction via photothermal synergy with ultrafine Pd nanoclusters supported on mesoporous TiO2. Chinese Journal of Structural Chemistry, 2024, 43(7): 100305-100305. doi: 10.1016/j.cjsc.2024.100305

    15. [15]

      Junxin LiChao ChenYuzhen DongJian LvJun-Mei PengYuan-Ye JiangDaoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732

    16. [16]

      Bowen WangLongwu SunQianqian CaoXinzhi LiJianai ChenShizhao WangMiaolin KeFener Chen . Cu-catalyzed three-component CSP coupling for the synthesis of trisubstituted allenyl phosphorothioates. Chinese Chemical Letters, 2024, 35(12): 109617-. doi: 10.1016/j.cclet.2024.109617

    17. [17]

      Yuhan LiuJingyang ZhangGongming YangJian Wang . Highly enantioselective carbene-catalyzed δ-lactonization via radical relay cross-coupling. Chinese Chemical Letters, 2025, 36(1): 109790-. doi: 10.1016/j.cclet.2024.109790

    18. [18]

      Zheyu LiHuwei LiYao LiXinyu FuHongxia YueQingxing YangJing FengXinyu WangHongjie Zhang . The effect of electron-phonon coupling on the photoluminescence properties of zinc-based halides. Chinese Chemical Letters, 2025, 36(4): 109800-. doi: 10.1016/j.cclet.2024.109800

    19. [19]

      Wenyi MeiLijuan XieXiaodong ZhangCunjian ShiFengzhi WangQiqi FuZhenjiang ZhaoHonglin LiYufang XuZhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825

    20. [20]

      Huipeng Zhao Xiaoqiang Du . Polyoxometalates as the redox anolyte for efficient conversion of biomass to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(2): 100246-100246. doi: 10.1016/j.cjsc.2024.100246

Metrics
  • PDF Downloads(0)
  • Abstract views(735)
  • HTML views(19)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return