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
  • [31] Biginelli Synthesis of Regioisomeric 5,6-Dihydro-4H-benzo[4,5]imidazo[1,2-a]pyranopyrimidin-4-ones
    I. V. Kanevskaya
    A. S. Bondartsova
    O. V. Fedotova
    [J]. Russian Journal of Organic Chemistry, 2020, 56 : 1753 - 1757
  • [32] Silica sulfuric acid/ethylene glycol as an efficient catalyst for the synthesis of benzo[4,5]imidazo[1,2-a]pyrimidine-3-carbonitrile derivatives
    Basyouni, Wahid M.
    Abbas, Samir Y.
    Abdelazeem, Nagwa M.
    El-Bayouki, Khairy A. M.
    El-Kady, Mohamed Y.
    [J]. SYNTHETIC COMMUNICATIONS, 2019, 49 (22) : 3112 - 3120
  • [33] Design, synthesis, and application of 1H-imidazol-3-ium trinitromethanide {[HIMI]C(NO2)3} as a recyclable nanostructured ionic liquid (NIL) catalyst for the synthesis of imidazo[1,2-a]pyrimidine-3-carbonitriles
    Yarie, Meysam
    Zolfigol, Mohammad Ali
    Baghery, Saeed
    Khoshnood, Abbas
    Alonso, Diego A.
    Kalhor, Mehdi
    Bayat, Yadollah
    Asgari, Asiye
    [J]. JOURNAL OF THE IRANIAN CHEMICAL SOCIETY, 2018, 15 (10) : 2259 - 2270
  • [34] AN ECO-FRIENDLY ULTRASOUND-ASSISTED ONE-POT THREE-COMPONENT SYNTHESIS OF 1,4-DIHYDROPYRIMIDO [1,2-A]BENZIMIDAZOLE DERIVATIVES CATALYZED BY MAGHNITE-H+
    Ben Messaoud, Hadda
    Benlahreche, Boumadiene
    Djemoui, Amar
    Souli, Lahcene
    Lahrech, Mokhtar Boualem
    [J]. HETEROCYCLIC LETTERS, 2023, 13 (03): : 449 - 457
  • [35] SILICA SULFURIC ACID PROMOTED ONE-POT SYNTHESIS OF BENZO[4,5]IMIDAZO[1,2-a]PYRIMIDINE DERIVATIVES UNDER SOLVENT-FREE CONDITIONS
    Wu, Liqiang
    Yan, Fulin
    Yang, Chunguang
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF ETHIOPIA, 2010, 24 (03) : 417 - 423
  • [36] Thiamine hydrochloride (VB1)-catalyzed one-pot synthesis of (E)-N-benzylidene-2-phenyl-1H-benzo[d]imidazo[1,2-a]imidazol-3-amine derivatives
    Chen, Fanglei
    Lei, Min
    Hu, Lihong
    [J]. TETRAHEDRON, 2013, 69 (14) : 2954 - 2960
  • [37] Synthesis and Tautomeric Structure of Tris(arylazo) Derivatives of Novel 1H-Bis-imidazo[1,2-b:2′,1′-e]pyrazole Ring System
    Shawali, Ahmad Sami
    Farghaly, Thoraya A.
    Shehata, Mohamed R.
    Hussein, Shadia M.
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2015, 52 (02) : 545 - 550
  • [38] Synthesis and tautomeric structure of novel 3-arylazo-imidazo[1,2-b]pyrazolo[4,3-d]pyridazines
    Farghaly, Thoraya A.
    Shawali, Ahmad Sami
    [J]. JOURNAL OF CHEMICAL RESEARCH, 2012, (05) : 296 - 299
  • [39] High chemoselectivity of C=S dipolarophile in 1,3-dipolar cycloaddition of nitrilimines and 1,1,4-triazepin-5-one derivatives: experimental, theoretical and X-ray study
    Azzouzi, S
    El Messaoudi, M
    Esseffar, M
    Jalal, R
    Cano, MH
    Apreda-Rojas, MDC
    Domingo, LR
    [J]. JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (06) : 522 - 528
  • [40] One-pot microwave assisted synthesis under green chemistry conditions, antioxidant screening, and cytotoxicity assessments of benzimidazole Schiff bases and pyrimido[1,2-a]benzimidazol-3(4H)-ones
    Neochoritis, Constantinos G.
    Zarganes-Tzitzikas, Tryfon
    Tsoleridis, Constantinos A.
    Stephanidou-Stephanatou, Julia
    Kontogiorgis, Christos A.
    Hadjipavlou-Litina, Dimitra J.
    Choli-Papadopoulou, Theodora
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) : 297 - 306