A facile synthesis of the novel thiazolo[3,2-a]pyrimidine derivatives

被引：16
|
作者：
Studzinska, Renata [1 ]
Wroblewski, Marcin [1 ]
Karczmarska-Wodzka, Aleksandra [1 ]
Kolodziejska, Renata [1 ]
机构：
[1] Nicolaus Copernicus Univ Torun, Coll Med Bydgoszcz, Dept Gen Chem, PL-85626 Bydgoszcz, Poland
来源：
TETRAHEDRON LETTERS | 2014年 / 55卷 / 07期
关键词：
Thiazolo[3,2-a]pyrimidine derivatives; 2-Halomethylthiazolo[3,2-a]pyrimidine derivatives; Organic synthesis; Thiazole ring closure; Substitution reaction; Elimination reaction; RITANSERIN;
D O I：
10.1016/j.tetlet.2014.01.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
2-Bromomethyl- and 2-iodomethyl-2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones are prepared via the reaction of 3-allyl-2-thiouracil derivatives with bromine or iodine chloride, respectively. The 6-bromo and 6-nitro derivatives are synthesized by an electrophilic substitution at C-6 of the thiazolopyrimidine system. As a result, novel 2,3-dihydrothiazolo[3,2-a]pyrimidin-5-one derivatives are obtained. Hydrogen halide elimination from the 2-halomethy1-2,3-dihydrothiazolo[3,2-a]pyrimidin-5-ones is also reported. (C) 2014 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1384 / 1386
页数：3
相关论文
共 50 条
  • [1] Synthesis of Novel Thiazolo[3,2-a]pyrimidine Compounds
    Zeng, Rongjin
    Zhou, Zaichun
    Wang, Zhaoxu
    Li, Xiaofang
    Chen, Zhong
    Yu, Xianyong
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2009, 29 (03) : 470 - 475
  • [2] SYNTHESIS AND STRUCTURAL EVALUATIONS OF THIAZOLO[3,2-A]PYRIMIDINE DERIVATIVES
    BALKAN, A
    ERTAN, M
    BURGEMEISTER, T
    ARCHIV DER PHARMAZIE, 1992, 325 (08) : 499 - 501
  • [3] Synthesis of thiazolo [3,2-a] pyrimidine derivatives as a biologically active heterocycles
    Parmar, JM
    Parikh, AR
    HETEROCYCLIC COMMUNICATIONS, 1998, 4 (05) : 463 - 466
  • [4] Synthesis and Characterization of Novel Thiazolo[3,2-a]pyrimidine Derivatives and Evaluation of Antioxidant and Cytotoxic Activities
    Khalilpour, Asieh
    Asghari, Sakineh
    Pourshab, Maryam
    CHEMISTRY & BIODIVERSITY, 2019, 16 (05)
  • [5] Synthesis and Antiproliferative Activity of Novel Thiazolo[3,2-a]pyrimidine Derivates
    Zhang, Lei
    Lin, Ya
    Wang, Jing
    Zhu, Xinling
    Yao, Qiuli
    Yao, Qizheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2015, 35 (02) : 497 - 504
  • [6] STUDIES ON PYRIMIDINE DERIVATIVES AND RELATED COMPOUNDS .44. SYNTHESIS OF THIAZOLO[3,2-A]PYRIMIDINE DERIVATIVES
    TAKAMIZA.A
    HIRAI, K
    ISHIBA, T
    MATSUMOT.Y
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1967, 15 (06) : 731 - +
  • [7] Synthesis, characterization and biological evaluation of fused thiazolo[3,2-a] pyrimidine derivatives
    Banothu, Janardhan
    Khanapur, Manjulatha
    Basavoju, Srinivas
    Bavantula, Rajitha
    Narra, Muralikrishna
    Abbagani, Sadanandam
    RSC ADVANCES, 2014, 4 (44): : 22866 - 22874
  • [8] Synthesis and crystal structure analysis of two thiazolo[3,2-a]pyrimidine derivatives
    Nagarajaiah, H.
    Khazi, M. I. A.
    Khan, A. Y.
    Fathima, N.
    Khazi, I. A. M.
    Begum, N. S.
    JOURNAL OF STRUCTURAL CHEMISTRY, 2014, 55 (08) : 1521 - 1526
  • [9] Synthesis and crystal structure analysis of two thiazolo[3,2-a]pyrimidine derivatives
    H. Nagarajaiah
    M. I. A. Khazi
    A. Y. Khan
    N. Fathima
    I. A. M. Khazi
    N. S. Begum
    Journal of Structural Chemistry, 2014, 55 : 1521 - 1526
  • [10] THIAZOLO[3,2-A]PYRIMIDINE DERIVATIVES AS CALCIUM-ANTAGONISTS
    BALKAN, A
    UMA, S
    ERTAN, M
    WIEGREBE, W
    PHARMAZIE, 1992, 47 (09): : 687 - 688
12345