A convenient one-pot synthesis of 2-benzimidazolyl-thioacetophenones and thiazolo[3,2-a]benzimidazoles

被引:24
|
作者
Sarhan, AEAO [1 ]
ElSherief, HAH [1 ]
Mahmoud, AM [1 ]
机构
[1] ASSIUT UNIV,FAC SCI,DEPT CHEM,ASSIUT 71516,EGYPT
关键词
D O I
10.1016/0040-4020(96)00569-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Mercaptobenzimidazole (1) reacts with aromatic ketones 2a-d in acidified acetic acid giving 2-benzimidazolylthioacetophenones 3a-d. which on cyclization yield thiazolo[3,2-a]benzimidazoles 4a-d. Acetylation of 3a,d gave the N-acetyl derivatives 5a,d. Cyclization of 3a-d or 5d in acetic anhydride or acetic anhydride/pyridine mixture afforded 6a-d. While reaction of 1 with aliphatic or alicyclic ketones gave directly 2,3-disubstituted thiazolo[3.2-a]benzimidazoles 7a-f and 8a-d respectively. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:10485 / 10496
页数:12
相关论文
共 50 条
  • [1] Convenient method for synthesis of thiazolo[3,2-a]pyrimidine derivatives in a one-pot procedure
    Singh, Sukhdeep
    Schober, Andreas
    Gebinoga, Michael
    Gross, G. Alexander
    TETRAHEDRON LETTERS, 2011, 52 (29) : 3814 - 3817
  • [2] Efficient regioselective one-pot synthesis of partially hydrogenated thiazolo[3,2-a]pyridines
    Krauze, A
    Popelis, J
    Duburs, G
    TETRAHEDRON, 1998, 54 (31) : 9161 - 9168
  • [3] Unequivocal synthesis of substituted thiazolo[3,2-a]benzimidazoles
    Rewcastle, Gordon W.
    ARKIVOC, 2020, : 214 - 227
  • [4] Expeditious one-pot synthesis of highly substituted thiazolo[3,2-a]pyridines involving chromones
    Terzidis, Michael A.
    Stephanidou-Stephanatou, Julia
    Tsoleridis, Constantinos A.
    Terzis, Aristides
    Raptopoulou, Catherine P.
    Psycharis, Vassilis
    TETRAHEDRON, 2010, 66 (04) : 947 - 954
  • [5] A convenient one-pot synthesis of 2-substituted benzimidazoles
    Trivedi, R
    De, SK
    Gibbs, RA
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2006, 245 (1-2) : 8 - 11
  • [6] CONVENIENT SYNTHESIS OF 3-METHYLTHIAZOLO[3,2-A]BENZIMIDAZOLES, 3-BENZYLTHIAZOLO[3,2-A]BENZIMIDAZOLES, AND 4-PHENYLTHIAZENO[3,2-A]BENZIMIDAZOLES
    BALASUBRAMANIAN, KK
    NAGARAJAN, R
    SYNTHESIS-STUTTGART, 1976, (03): : 189 - 189
  • [7] One-pot synthesis of thiazolo[3,2-a]pyrimidine derivatives, their cytotoxic evaluation and molecular docking studies
    Sekhar, Thuraka
    Thriveni, Pinnu
    Venkateswarlu, Annavarapu
    Daveedu, Thathapudi
    Peddanna, Kotha
    Sainath, Sri Bhashyam
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2020, 231 (231)
  • [8] New synthesis of 2,3-dihydro-thiazolo[3,2-a]benzimidazoles
    F. A. Khaliullin
    E. E. Klen
    Chemistry of Heterocyclic Compounds, 2009, 45 : 876 - 877
  • [9] CYCLOCONDENSATION OF NOVEL THIAZOLO[3,2-A]BENZIMIDAZOLES
    SARHAN, AAO
    HOZIEN, ZA
    ELSHERIEF, HAH
    MAHMOUD, AM
    POLISH JOURNAL OF CHEMISTRY, 1995, 69 (11) : 1479 - 1483
  • [10] One-Pot Green Synthesis of Thiazolo[3,2-a]pyridine Derivatives via Tandem Cyclization in Aqueous Media
    Boominathan, Muthusamy
    Nagaraj, Muthupandi
    Maheshwaran, Chellaiah
    Muthusubramanian, Shanmugam
    Bhuvanesh, Nattamai
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (01) : 244 - 248