L-Proline-catalyzed three-component synthesis of condensed imidazoles

被引:13
|
作者
Damavandi, Saman [1 ]
Sandaroos, Reza [2 ]
机构
[1] Islamic Azad Univ, Sarvestan Branch, Dept Chem, Sarvestan, Iran
[2] Birjand Univ, Dept Chem, Fac Sci, Birjand, Iran
关键词
Imidazo[4,5-b]indole; Imidazo[4,5-f]phenanthroline; L-Proline; ONE-POT SYNTHESIS; TETRASUBSTITUTED IMIDAZOLES; IONIC LIQUID;
D O I
10.1016/j.arabjc.2011.12.004
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A one-pot, efficient and high yielding procedure for the synthesis of 3,4-dihydro-2-arylimidazo[4,5-b]indole and 2-aryl-1H-imidazo[4,5-f][1,10]phenanthroline is reported. The procedure proceeded by the multicomponent reaction of aromatic aldehydes, indoline-2,3-dione or 1,10-phenanthroline-5,6-dione and ammonium acetate catalyzed by L-proline under ultrasonic irradiation. Conveniency, simplicity, rapidity and cleanliness of the procedure for the synthesis of imidazole derivatives are the advantages of this study. (C) 2011 Production and hosting by Elsevier B.V. on behalf of King Saud University.
引用
收藏
页码:S1138 / S1143
页数:6
相关论文
共 50 条
  • [1] L-proline-catalyzed one-pot three-component reaction for the synthesis of β-alkoxy ketones
    Dodda, Rajasekhar
    Zhao, Cong-Gui
    [J]. SYNTHESIS-STUTTGART, 2006, (19): : 3238 - 3242
  • [2] L-Proline-catalyzed three-component domino reactions for the synthesis of highly functionalized pyrazolo[3,4-b]pyridines
    Gunasekaran, Pethaiah
    Prasanna, Pitchaimani
    Perumal, Subbu
    [J]. TETRAHEDRON LETTERS, 2014, 55 (02) : 329 - 332
  • [3] L-Proline-catalyzed three-component domino reactions in the regioselective synthesis of novel densely functionalized pyrazolo[3,4-b]pyridines
    Gunasekaran, Pethaiah
    Indumathi, Sethuraman
    Perumal, Subbu
    [J]. RSC ADVANCES, 2013, 3 (22) : 8318 - 8325
  • [4] L-Proline-Catalyzed Three-Component Domino [3+2+1] Annulation for the Regio- and Diastereoselective Synthesis of Highly Substituted Thienothiopyrans Containing Three or Four Stereocenters
    Indumathi, Sethuraman
    Perumal, Subbu
    Carlos Menendez, J.
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (02): : 472 - 475
  • [5] Ag-Catalyzed Tandem Three-Component Reaction toward the Synthesis of Multisubstituted Imidazoles
    Wang, Changcheng
    Lai, Jialin
    Chen, Cantao
    Li, Xuechen
    Cao, Hua
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (24): : 13740 - 13745
  • [6] An Efficient Synthesis of Polyfunctionalized Indole Derivatives via Three-component Domino Reaction Catalyzed by L-Proline
    Fu, Lei
    Lin, Wei
    Huang, Zhi-Bin
    Shi, Da-Qing
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (04) : 1075 - 1081
  • [7] L-Proline-catalyzed multicomponent synthesis of 3-indole derivatives
    He, Yan-Hong
    Cao, Jian-Fei
    Li, Rui
    Xiang, Yang
    Yang, Da-Cheng
    Guan, Zhi
    [J]. TETRAHEDRON, 2015, 71 (49) : 9299 - 9306
  • [8] Synthesis of pyrrolobenzoxazepinones by CuI/L-proline-catalyzed intramolecular coupling reactions
    Huang, Aiping
    Feng, Lei
    Qiao, Zhi
    Yu, Wei
    Zheng, Qingqing
    Ma, Chen
    [J]. TETRAHEDRON, 2013, 69 (02) : 642 - 646
  • [9] CuI/L-proline-catalyzed synthesis of vinyl sulfides in 95% alcohol
    Guo, Sheng-Rong
    Yuan, Yan-Qin
    [J]. SYNTHETIC COMMUNICATIONS, 2008, 38 (16) : 2722 - 2730
  • [10] L-Proline catalyzed efficient and convenient synthesis of substituted 2H-chromenes by three-component reaction
    Rao, L. Chandrasekhara
    Meshram, H. M.
    Kumar, N. Satish
    Rao, N. Nageswara
    Babu, N. Jagadeesh
    [J]. TETRAHEDRON LETTERS, 2014, 55 (06) : 1127 - 1131