Synthesis and X-ray crystal structure of pyrrolo[1,2-a]benzimidazoles

被引：13
|
作者：
Awadallah, Adel M.
Seppelt, Konrad
Shorafa, Hashem
机构：
[1] Islam Univ, Fac Sci, Dept Chem, Gaza, Palestine, Israel
[2] Free Univ Berlin, Inst Chem, D-14195 Berlin, Germany
来源：
TETRAHEDRON | 2006年 / 62卷 / 33期
关键词：
nitrilimines; 2-cyanomethylbenzimidazole; 2-aminobenzimidazole; pyrrolo[1,2-alpha]benzimidazole;
D O I：
10.1016/j.tet.2006.05.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Reaction of nitrilimines 1 with 2-cyanomethylbenzimidazole 2 gave the 3-arylazo-2-methylpyrrolo[1,2-a]benzimidazole 4a rather than the reported 2-arylazo-3-methylpyrrolo[1,2-a]benzimidazole 3a. The correct structure of the product was determined using X-ray crystal structure analysis. The similar reaction of nitrilimines with 2-aminobenzimidazole 5 gave the acyclic nucleophilic addition product 6. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7744 / 7746
页数：3
相关论文
共 50 条
  • [1] SYNTHESIS AND APPLICATION OF IMIDAZOLE DERIVATES - SYNTHESIS OF PYRROLO[1,2-A]BENZIMIDAZOLES AND AZEPINO[1,2-A]BENZIMIDAZOLES
    OHTA, S
    NARITA, Y
    YUASA, T
    HATAKEYAMA, S
    KOBAYASHI, M
    KAIBE, K
    KAWASAKI, I
    YAMASHITA, M
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1991, 39 (11) : 2787 - 2792
  • [2] Unexpected formation of pyrrolo[1,2-a]quinoxaline derivatives during the multicomponent synthesis of pyrrolo[1,2-a]benzimidazoles
    Nicolescu, Alina
    Deleanu, Calin
    Georgescu, Emilian
    Georgescu, Florentina
    Iurascu, Ana-Maria
    Shova, Sergiu
    Filip, Petru
    TETRAHEDRON LETTERS, 2013, 54 (11) : 1486 - 1488
  • [3] Synthesis, X-ray crystal structure and optical properties of novel 2-aryl-3-ethoxycarbonyl-4-phenylpyrido[1,2-a]benzimidazoles
    Chen, Xia
    Yang, He
    Ge, Yanqing
    Feng, Lei
    Jia, Jiong
    Wang, Jianwu
    LUMINESCENCE, 2012, 27 (05) : 382 - 389
  • [4] SIMPLE SYNTHESES OF PYRIDO[1,2-A]BENZIMIDAZOLES AND OF 4H-PYRROLO[1,2-A]BENZIMIDAZOLES
    GALONS, H
    COMBETFARNOUX, C
    MIOCQUE, M
    PHARMAZIE, 1987, 42 (08): : 548 - 549
  • [5] A facile synthesis of pyrrolo[1,2-a]benzimidazoles and pyrazolo[3,4:4′,3′]pyrrolo[1,2-a]benzimidazole derivatives
    Elwan, NM
    TETRAHEDRON, 2004, 60 (05) : 1161 - 1166
  • [6] AZOCOMBINATION, NITRATION AND NITROSYLATION OF PYRROLO (1,2-A) BENZIMIDAZOLES
    BABICHEV, FS
    KUTROV, GP
    KORNILOV, MY
    UKRAINSKII KHIMICHESKII ZHURNAL, 1970, 36 (09): : 909 - &
  • [7] A FACILE SYNTHESIS OF PYRROLO[1,2-A]PYRIMIDINES AND PYRROLO[1,2-A]IMIDAZOLES
    ROSS, JR
    VISHWAKARMA, LC
    SOWELL, JW
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (03) : 661 - 665
  • [8] Synthesis and X-ray structure of a new pyrrolo[1,2-b]pyridazine derivative
    Caira, MR
    Dumitrascu, F
    Draghici, C
    Dumitrescu, D
    Cristea, M
    MOLECULES, 2005, 10 (02): : 360 - 366
  • [9] A facile synthesis of pyrrolo [1,2-a] imidazoles and pyrrolo-[1,2-a] pyrimidines
    Singh, OM
    Ahmed, MF
    Dinesh, H
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2005, 15 (01) : 87 - 88
  • [10] A pyrrolo-tetrathiafulvalene cage: Synthesis and X-ray crystal structure
    Nielsen, KA
    Jeppesen, JO
    Levillain, E
    Thorup, N
    Becher, J
    ORGANIC LETTERS, 2002, 4 (24) : 4189 - 4192
12345