Synthesis of 2-(3-furyl)-1H-benzimidazoles from 2-phenacyl-1H- benzimidazoles

被引:0
|
作者
Dzvinchuk I.B. [1 ]
Lozinskii M.O. [1 ]
机构
[1] Institute of Organic Chemistry, National Academy of Sciences of Ukraine
来源
Chem. Heterocycl. Compd. | 2007年 / 11卷 / 1390-1396期
关键词
Benzimidazoles; C-alkylation; Cyclocondensation; Furans; Phenacyl bromides; Selectivity;
D O I
10.1007/s10593-007-0215-6
中图分类号
学科分类号
摘要
C-Alkylation at the active methylene group of 2-phenacyl-1H-benzimidazoles with phenacyl bromides proceeds highly selectively with the formation of the corresponding 1,4-diketones, which on heating with hydrochloric acid are cyclized with the formation of the previously unknown 2-(2,5-diaryl-3-furyl)-1H- benzimidazoles. © 2007 Springer Science+Business Media, Inc.
引用
收藏
页码:1390 / 1396
页数:6
相关论文
共 50 条
  • [31] AN ADVANTAGEOUS SYNTHESIS OF 2-SUBSTITUTED BENZIMIDAZOLES USING POLYPHOSPHORIC ACID - 2-(PYRIDYL)-1H-BENZIMIDAZOLES, 1-ALKYL-(1H-BENZIMIDAZOL-2-YL)PYRIDINIUM SALTS, THEIR HOMOLOGS AND VINYLOGUES
    ALCALDE, E
    DINARES, I
    PEREZGARCIA, L
    ROCA, T
    SYNTHESIS-STUTTGART, 1992, (04): : 395 - 398
  • [32] Lead optimization of 2-(piperidin-3-yl)-1H-benzimidazoles: Identification of 2-morpholin- and 2-thiomorpholin-2-yl-1H-benzimidazoles as selective and CNS penetrating H1-antihistamines for insomnia
    Ravula, Satheesh Babu
    Yu, Jinghua
    Tran, Joe A.
    Arellano, Melissa
    Tucci, Fabio C.
    Moree, Wilna J.
    Li, Bin-Feng
    Petroski, Robert E.
    Wen, Jianyun
    Malany, Siobhan
    Hoare, Samuel R. J.
    Madan, Ajay
    Crowe, Paul D.
    Beaton, Graham
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (01) : 421 - 426
  • [33] Facile and Eco-friendly Synthesis of 2-(2-Methoxyethyl sulfanyl)-1H-benzimidazoles and Their Antimicrobial Screening
    Varaprasad, Dasari
    Rao, Gangula Mohan
    Rao, Sumangala
    Chakravarthy, Akula Kalyan
    Vijayakumar, Baru
    ASIAN JOURNAL OF CHEMISTRY, 2009, 21 (06) : 4251 - 4257
  • [34] Synthesis and fungicidal activity of novel 2-(2-alkylthio-6-phenylpyrimidin-4-yl)-1H-benzimidazoles
    Sun, Changxing
    Zhang, Shuai
    Qian, Ping
    Li, Ying
    Deng, Hao
    Ren, Wansheng
    Jiang, Lin
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 47
  • [35] Synthesis of pyrido[1,2-a]benzimidazoles from 2-acylmethyl-1H- benzimidazoles
    Dzvinchuk I.B.
    Turov A.V.
    Lozinskii M.O.
    Chemistry of Heterocyclic Compounds, 2006, 42 (7) : 929 - 934
  • [36] Synthesis of pyrido[1,2-a]-benzimidazoles from 2-acylmethyl-1H-benzimidazoles
    Dzvinchuk, I. B.
    Turov, A. V.
    Lozinskii, M. O.
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2006, (07): : 1073 - 1079
  • [37] Cyclocondensation of 2-(1-aryl-5-phenylpyrazol-4-yl)-1H-benzimidazoles with DMF dimethylacetal
    Dzvinchuk, IB
    Lozinskii, MO
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2005, (09): : 1404 - 1405
  • [38] Cyclocondensation of 2-(1-Aryl-5-phenylpyrazol-4-yl)-1H-benzimidazoles with DMF Dimethylacetal
    I. B. Dzvinchuk
    M. O. Lozinskii
    Chemistry of Heterocyclic Compounds, 2005, 41 (9) : 1199 - 1200
  • [39] Preparative synthesis of 2-[3-alkoxy-4-(hydroxy, alkoxy, acyloxy)phenyl]-1H-benzimidazoles proceeding from substituted benzaldehydes
    Dikusar, E. A.
    Potkin, V. I.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (02) : 268 - 274
  • [40] Preparative synthesis of 2-[3-alkoxy-4-(hydroxy, alkoxy, acyloxy)phenyl]-1H-benzimidazoles proceeding from substituted benzaldehydes
    E. A. Dikusar
    V. I. Potkin
    Russian Journal of Organic Chemistry, 2010, 46 : 268 - 274