A convenient [hydroxy(tosyloxy)iodo]benzene-mediated one-pot synthesis of 2-arylimidazo[2,1-b]benzothiazoles

被引:12
|
作者
Sumran, Garima [1 ]
Aggarwal, Ranjana [2 ]
机构
[1] DAV Coll Lahore, Dept Chem, Ambala City 134002, Haryana, India
[2] Kurukshetra Univ, Dept Chem, Kurukshetra 136119, Haryana, India
关键词
imidazo[2,1-b]benzothiazoles; hydroxy(tosyloxy)iodo]benzene; hypervalent iodine; 2-amino-6-(substituted)benzothiazoles; alpha-tosyloxyketones; REGIOSELECTIVE SYNTHESIS; BIOLOGICAL EVALUATION; EFFICIENT SYNTHESIS; SOLVENT-FREE; AGENTS; DERIVATIVES; INHIBITORS; MOIETY; WATER;
D O I
10.1080/17415993.2014.996221
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Several 2-arylimidazo[2,1-b]benzothiazoles (4) have been conveniently synthesized in one-pot reactions via alpha-tosyloxylation of enolizable ketones (1) using [hydroxy(tosyloxy)iodo]benzene 2 in acetonitrile, followed by treatment with 2-amino-6-(substituted)benzothiazoles (3). The present protocol offers several advantages towards general access of 2-arylimidazo[2,1-b]benzothiazoles, including an intriguing alternative to the literature protocols, a readily available nontoxic reagent, operational simplicity and an environmentally benign procedure.
引用
收藏
页码:170 / 177
页数:8
相关论文
共 50 条
  • [1] Hypervalent iodine in the synthesis of bridgehead heterocycles: A facile route to the synthesis of 6-arylimidazo[2,1-b]thiazoles using [hydroxy(tosyloxy)iodo]benzene
    Aggarwal, R
    Sumran, G
    SYNTHETIC COMMUNICATIONS, 2006, 36 (07) : 875 - 879
  • [2] A facile [hydroxy(tosyloxy)iodo]benzene mediated synthesis of 2-arylimidazo[1,2-a]pyrimidines and their conversion into 3-bromo-2-arylimidazo[1,2-a]pyrimidines
    Aggarwal, Ranjana
    Sumran, Garima
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2006, 45 (12): : 2690 - 2695
  • [3] Synthesis and biological evaluation of novel Mannich bases of 2-arylimidazo[2,1-b]benzothiazoles as potential anti-cancer agents
    Kumbhare, Ravindra M.
    Kumar, K. Vijay
    Ramaiah, M. Janaki
    Dadmal, Tulshiram
    Pushpavalli, S. N. C. V. L.
    Mukhopadhyay, Debasmita
    Divya, B.
    Devi, T. Anjana
    Kosurkar, Umesh
    Pal-Bhadra, Manika
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (09) : 4258 - 4266
  • [4] AN EFFICIENT ONE-POT SYNTHESIS OF AZULENO [2,1-b]PYRIDAZINES
    Wang, Dao-Lin
    Ma, Jian
    Shi, Xiao-Ce
    Wu, Jian-Ying
    HETEROCYCLES, 2016, 92 (01) : 133 - 140
  • [5] HETEROCYCLIC SYSTEM CONTAINING BRIDGEHEAD NITROGEN ATOM - FACILE ONE-POT SYNTHESIS OF IMIDAZO[2,1-B] THIAZOLES AND THIAZOLO[3,2-A]PYRIMIDINES USING [HYDROXY(PARA-TOSYLOXY)IODO]BENZENE
    MOHAN, J
    VERMA, P
    SINGH, V
    SYNTHETIC COMMUNICATIONS, 1992, 22 (09) : 1293 - 1298
  • [7] Hypervalent iodine in synthesis. 48. A one-pot convenient procedure for the synthesis of 2-mercaptothiazoles by cyclocondensation of ketones with [hydroxy(tosyloxy)iodo]-benzene and ammonium dithiocarbamate
    Zhang, PF
    Chen, ZC
    SYNTHETIC COMMUNICATIONS, 2001, 31 (03) : 415 - 420
  • [8] Efficient regioselective synthesis of triheterocyclic compounds:: imidazo[2,1-b]benzothiazoles, pyrimido[2,1-b]benzothiazolones and pyrimido[2,1-b]benzothiazoles
    Landreau, C
    Deniaud, D
    Evain, M
    Reliquet, A
    Meslin, JC
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (06): : 741 - 745
  • [9] IMIDAZO[2,1-B]BENZOTHIAZOLES .2. SYNTHESIS AND ANTIINFLAMMATORY ACTIVITY OF SOME IMIDAZO[2,1-B]BENZOTHIAZOLES
    ELSHORBAGI, AN
    SAKAI, S
    ELGENDY, MA
    OMAR, N
    FARAG, HH
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1989, 37 (11) : 2971 - 2975
  • [10] 2-Arylimidazo[2,1-b]benzothiazoles: A new family of amyloid binding agents with potential for PET and SPECT imaging of Alzheimer's brain
    Alagille, David
    DaCosta, Herve
    Baldwin, Ronald M.
    Tamagnan, Gilles D.
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2011, 21 (10) : 2966 - 2968