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
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 48 条
  • [1] Pyrimido[1,2-a]benzimidazoles: synthesis and perspective of their pharmacological use
    Victor V. Fedotov
    Vladimir L. Rusinov
    Evgeny N. Ulomsky
    Evgeny M. Mukhin
    Evgeny B. Gorbunov
    Oleg N. Chupakhin
    Chemistry of Heterocyclic Compounds, 2021, 57 : 383 - 409
  • [2] Regiodirected synthesis of polyfluoro-alkylated pyrimido[1,2-a]benzimidazoles
    Goryaeva, M. V.
    Burgart, Ya. V.
    Saloutin, V. I.
    Chupakhin, O. N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2012, 48 (02) : 372 - 376
  • [3] Regiodirected synthesis of polyfluoro-alkylated pyrimido[1,2-a]benzimidazoles
    M. V. Goryaeva
    Ya. V. Burgart
    V. I. Saloutin
    O. N. Chupakhin
    Chemistry of Heterocyclic Compounds, 2012, 48 : 372 - 376
  • [4] SC2WT Pyrimido[1,2-a]benzimidazoles: synthesis and perspective of their pharmacological use
    Fedotov, Victor V.
    Rusinov, Vladimir L.
    Ulomsky, Evgeny N.
    Mukhin, Evgeny M.
    Gorbunov, Evgeny B.
    Chupakhin, Oleg N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (04) : 383 - 409
  • [5] Synthesis of pyrido[1,2-a]benzimidazoles and other fused imidazole derivatives with a bridgehead nitrogen atom
    Begunov, R. S.
    Ryzvanovich, G. A.
    RUSSIAN CHEMICAL REVIEWS, 2013, 82 (01) : 77 - 97
  • [6] Synthesis and characterization of some novel 2-(trifluoromethyl)pyrimido[1,2-a]benzimidazoles and pyrimido[1,2-a]benzimidazol-2H)-ones of biological interest
    Zanatta, Nilo
    Amaral, Simone S.
    Esteves-Souza, Andressa
    Echevarria, Aurea
    Brondani, Patricia B.
    Flores, Darlene C.
    Bonacorso, Hello G.
    Flores, Alex F. C.
    Martins, Marcos A. P.
    SYNTHESIS-STUTTGART, 2006, 14 (14): : 2305 - 2312
  • [7] Synthesis of Novel Diastereomer Pyrimido[1,2-a]Benzimidazoles by Using Silica Sulfuric Acid/Ethylene Glycol
    Basyouni, Wahid M.
    Abbas, Samir Y.
    Abdelazeem, Nagwa M.
    El-Bayouki, Khairy A. M.
    El-Kady, Mohamed Y.
    POLYCYCLIC AROMATIC COMPOUNDS, 2023, 43 (02) : 1192 - 1201
  • [8] Efficient Synthesis of Pyrimido[1,2-a]Benzimidazoles and Ethyl Pyrimido[1,2-a]Benzimidazole-3-Carboxylates Using Bronsted Acidic Ionic Liquid Supported on Nanoporous Na+-Montmorillonite
    Makhsous, Masoumeh
    Shirini, Farhad
    Seddighi, Mohadeseh
    Mazloumi, Masoumeh
    POLYCYCLIC AROMATIC COMPOUNDS, 2020, 40 (02) : 494 - 501
  • [9] 4H-Chromenes as 1,3-bielectrophiles in the reaction with 2-aminobenzimidazole: synthesis of pyrimido[1,2-a]benzimidazoles
    Vitaly А. Osyanin
    Dmitry V. Osipov
    Kirill S. Korzhenko
    Oleg P. Demidov
    Yuri N. Klimochkin
    Chemistry of Heterocyclic Compounds, 2021, 57 : 588 - 593
  • [10] 4H-Chromenes as 1,3-bielectrophiles in the reaction with 2-aminobenzimidazole: synthesis of pyrimido [1,2-a] benzimidazoles
    Osyanin, Vitaly A.
    Osipov, Dmitry, V
    Korzhenko, Kirill S.
    Demidov, Oleg P.
    Klimochkin, Yuri N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2021, 57 (05) : 588 - 593