Microwave-assisted Hantzsch thiazole synthesis of N-phenyl-4-(6-phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amines from the reaction of 2-chloro-1-(6-phenylimidazo[2,1-b]thiazol-5-yl)ethanones and thioureas

被引:19
|
作者
Kamila, Sukanta [1 ]
Mendoza, Kimberly [1 ]
Biehl, Edward R. [1 ]
机构
[1] So Methodist Univ, Dept Chem, Dallas, TX 75275 USA
关键词
Microwave irradiation; (6-Phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amine 2-chloro-1-(6-phenylimidazo[2,1-b]thiazol-5-yl)ethanones; 6-Phenylimidazo[2,1-b]thiazoles; ONE-POT SYNTHESIS; DERIVATIVES; ANTITUMOR; EFFICIENT;
D O I
10.1016/j.tetlet.2012.06.116
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N-Phenyl-4-(6-phenylimidazo[2,1-b]thiazol-5-yl)thiazol-2-amines (6a-q) have been synthesized by the Hantzsch thiazole reaction of 2-chloro-1-(6-phenylimidazo[2,1-b]thiazol-5-yl)ethanones (4a-e) with suitably substituted thioureas using microwave heating. The ethanones (4a-e) were prepared by the reaction of 6-phenylimidazo[2,1-b]thiazoles (3a-e) with chloroacetylchloride in refluxing 1,4-dioxane whereas the thiazoles (3a-e) were synthesized by the reaction of 2-bromo-1-phenylethanones (2a-e) with thiazol-2-amine in refluxing acetone. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4921 / 4924
页数:4
相关论文
共 50 条
  • [21] Chloro(ethylenediamine)(6-phenylimidazo-[2,1-b]thiazole-N-7)platinum(II) nitrate
    Arvanitis, GM
    Griffitts, AE
    Baffic, SP
    Ho, DM
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1996, 52 : 319 - 321
  • [22] STUDIES ON CHEMISTRY OF 2,3,5,6-TETRAHYDRO-6-PHENYLIMIDAZO[2,1-B]-THIAZOLE .2. REACTION WITH NUCLEOPHILES
    BIGG, DCH
    PURVIS, SR
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1977, 14 (04) : 607 - 609
  • [23] Substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-ones and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones as hypoglycemic agents
    Aicher, TD
    Balkan, B
    Bell, PA
    Brand, LJ
    Cheon, SH
    Deems, RO
    Fell, JB
    Fillers, WS
    Fraser, JD
    Gao, JP
    Knorr, DC
    Kahle, GG
    Leone, CL
    Nadelson, J
    Simpson, R
    Smith, HC
    JOURNAL OF MEDICINAL CHEMISTRY, 1998, 41 (23) : 4556 - 4566
  • [24] Synthesis and Biological Evaluation of N-Phenyl-4-(pyridin-2-yl)-5-(1H-1,2,4-triazol-1-yl)thiazol-2-amines
    Zhang, Mu
    Luo, Xiai
    Zhu, Daizheng
    Zhang, Xuepeng
    Liu, Feng
    Fang
    Liu, Jianbing
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (09) : 1955 - 1959
  • [25] N-(3-oxo-1-thia-4-azaspiro[4.5]dec-4-yl)-6-phenylimidazo[2,1-b][1,3]thiazole3-acetamide hemihydrate
    Akkurt, Mehmet
    Yalcin, Serife Pinar
    Guezeldemirci, Nuray Ulusoy
    Buyukgungor, Orhan
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O810 - U1487
  • [26] Dichlorobis[(S)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole] nickel(II)
    Cabeza, JA
    del Río, I
    Sánchez-Vega, MG
    García-Granda, S
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : M1984 - M1985
  • [27] 7-Benzyl-3-methyl-6-phenylimidazo[2,1-b][1,3]thiazol-7-iumchloride0.75-hydrate
    Guo-Li, Huang
    Bo, Liu
    Jun-Feng, Kou
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1247 - +
  • [28] Synthesis and crystal structure analysis of 2-(4-fluorobenzyl)-6-phenylimidazo[2,1-b]- [1,3,4]thiadiazole and its chlorophenyl derivative
    Banu, Afshan
    Lamani, Ravi S.
    Khazi, I. A. M.
    Begum, Noor Shahina
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2014, 18 (05) : 371 - 378
  • [29] Derivatives of 5-(imidazo[2,1-b]thiazol-6-yl)-4-methylthiazol-2-amine new effective EGFR-kinase inhibitors
    Bunev, Alexander
    Sukhonosova, Elena
    Talina, Kristina
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 253
  • [30] Synthesis of imidazo[2,1-b]thiazol-5-amines using Groebke-Blackburn-Bienaymé multicomponent reaction (microreview)
    Longo Jr, Luiz S.
    Siqueira, Fernanda A.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2024, 60 (7-8) : 339 - 341