Regioselective synthesis of imidazo[1,5-a]quinoxalines and methyl N-phenylbenzimidats on an ionic liquid support

被引：57
作者：
Chen, Li-Hsun [1 ]
Kao, Chih-Hsien [1 ]
Dhole, Sandip [1 ]
Barve, Indrajeet J. [1 ]
Shen, Li-Ching [1 ]
Chung, Wen-Sheng [1 ]
Sun, Chung-Ming [1 ,2 ]
机构：
[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu 30010, Taiwan
[2] Kaohsiung Med Univ, Dept Med & Appl Chem, 100 Shih Chuan 1st Rd, Kaohsiung 80708, Taiwan
来源：
RSC ADVANCES | 2016年 / 6卷 / 80期
关键词：
D O I：
10.1039/c6ra11861e
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An ionic liquid (IL) supported, regioselective synthesis of imidazo[1,5-a]quinoxalines and methyl N-phenylbenzimidats under microwave conditions was reported. The IL-immobilized aromatic amines were reacted with various ketones and aliphatic aldehydes using an unconventional Pictet-Spengler reaction to generate polycyclic imidazo[1,5-a]quinoxalines. Alternatively, aromatic aldehydes afforded auto-oxidized imidazo[1,5-a]quinoxalines first which further converted to novel methyl N-phenylbenzimidats unexpectedly during the cleavage of the IL-support. In the reported strategy, rapidness is achieved through microwave conditions while the IL-support assists purification by simple precipitation.
引用
收藏
页码：76123 / 76127
页数：5
相关论文
共 22 条
  • [1] Synthesis of 1-aryl-substituted-4-chloroimidazo[1,2-a]quinoxalines catalyzed by PdCl2 in water
    Bakherad, Mohammad
    Keivanloo, Ali
    Samangooei, Shahrzad
    [J]. TETRAHEDRON LETTERS, 2012, 53 (12) : 1447 - 1449
  • [2] BMS-345541 is a highly selective inhibitor of IκB kinase that binds at an allosteric site of the enzyme and blocks NF-κB-dependent transcription in mice
    Burke, JR
    Pattoli, MA
    Gregor, KR
    Brassil, PJ
    MacMaster, JF
    McIntyre, KW
    Yang, XX
    Iotzova, VS
    Clarke, W
    Strnad, J
    Qiu, YP
    Zusi, FC
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (03) : 1450 - 1456
  • [3] Imidazoquinoxaline Src-family kinase p56Lck inhibitors:: SAR, QSAR, and the discovery of (S)-N-(2-chloro-6-methylphenyl)-2-(3-methyl-1-piperazinyl)imidazo[1,5-a]pyrido[3,2-e]pyrazin-6-amine (BMS-279700) as a potent and orally active inhibitor with excellent in vivo antiinflammatory activity
    Chen, P
    Doweyko, AM
    Norris, D
    Gu, HH
    Spergel, SH
    Das, J
    Moquin, RV
    Lin, J
    Wityak, J
    Iwanowicz, EJ
    McIntyre, KW
    Shuster, DJ
    Behnia, K
    Chong, S
    de Fex, H
    Pang, SH
    Pitt, S
    Shen, DR
    Thrall, S
    Stanley, P
    Kocy, OR
    Witmer, MR
    Kanner, SB
    Schieven, GL
    Barrish, JC
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (18) : 4517 - 4529
  • [4] Discovery and initial SAR of imidazoquinoxalines as inhibitors of the Src-family kinase p56Lck
    Chen, P
    Norris, D
    Iwanowicz, EJ
    Spergel, SH
    Lin, J
    Gu, HH
    Shen, ZQ
    Wityak, J
    Lin, TA
    Pang, SH
    De Fex, HF
    Pitt, S
    Shen, DR
    Doweyko, AM
    Bassolino, DA
    Roberge, JY
    Poss, MA
    Chen, BC
    Schieven, GL
    Barrish, JC
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2002, 12 (10) : 1361 - 1364
  • [5] THE PICTET-SPENGLER CONDENSATION - A NEW DIRECTION FOR AN OLD REACTION
    COX, ED
    COOK, JM
    [J]. CHEMICAL REVIEWS, 1995, 95 (06) : 1797 - 1842
  • [6] A modified strategy for Pictet-Spengler reaction leading to the synthesis of imidazoquinoxalines on solid phase
    Kundu, B
    Sawant, D
    Chhabra, R
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2005, 7 (02): : 317 - 321
  • [7] Update 1 of: Ionic Liquids in Heterocyclic Synthesis. The root paper of this title was published in Chem. Rev. 2008, 108 (6), 2015-2050
    Martins, Marcos A. P.
    Frizzo, Clarissa P.
    Tier, Aniele Z.
    Moreira, Dayse N.
    Zanatta, Nilo
    Bonacorso, Helio G.
    [J]. CHEMICAL REVIEWS, 2014, 114 (20) : PR1 - +
  • [8] Ionic-liquid-supported synthesis: A novel liquid-phase strategy for organic synthesis
    Miao, Weishi
    Chan, Tak Hang
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2006, 39 (12) : 897 - 908
  • [9] Exploration of ionic liquids as soluble supports for organic synthesis. Demonstration with a Suzuki coupling reaction
    Miao, WS
    Chan, TH
    [J]. ORGANIC LETTERS, 2003, 5 (26) : 5003 - 5005
  • [10] In vitro and in vivo anti-tumoral activities of imidazo[1,2-a] quinoxaline, imidazo[1,5-a] quinoxaline, and pyrazolo[1,5-a] quinoxaline derivatives
    Moarbess, Georges
    Deleuze-Masquefa, Carine
    Bonnard, Vanessa
    Gayraud-Paniagua, Stephanie
    Vidal, Jean-Remi
    Bressolle, Francoise
    Pinguet, Frederic
    Bonnet, Pierre-Antoine
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (13) : 6601 - 6610
123