Efficient and green synthesis of novel hexahydro-5H-thiazolo[2′,3′:2,3]pyrimido[4,5-b]quinoline derivatives

被引:6
作者
Tabibi, Tooba [1 ]
Esmaeili, Abbas Ali [1 ]
机构
[1] Ferdowsi Univ Mashhad, Fac Sci, Dept Chem, POB 9177948974, Mashhad, Razavi Khorasan, Iran
关键词
Three-component reaction; Catalyst-free synthesis; 5-Amino-2,3-dihydro-7H-thiazolo [3,2-alpha]pyrimidin-7-one; Hexahydro-5H-thiazolo[2 ',3 ':2,3]pyrimido[4,5-b]quinolines; MICROWAVE-ASSISTED SYNTHESIS; BIOLOGICAL EVALUATION; THIAZOLOPYRIMIDINE DERIVATIVES; PYRIMIDINE; 1,4-DIHYDROPYRIDINES; THIOPYRIMIDINE; ANTIBACTERIAL; INHIBITION; LIGANDS;
D O I
10.1007/s11030-022-10439-z
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Herein, we report a catalyst-free, one-pot three-component reaction of 5-amino-2,3-dihydro-7H-thiazolo[3,2-a]pyrimidin-7-one, aromatic aldehyde, and dimedone in ethylene glycol as a green solvent at 100 degrees C for the easy access of hexahydro-5H-thiazolo[2',3':2,3]pyrimido[4,5-b]quinoline. Catalyst-free, green solvent, simple procedure, mild reaction conditions, easy work-up procedure, and good to excellent yields are the significant advantages of this protocol. [GRAPHICS] .
引用
收藏
页码:477 / 486
页数:10
相关论文
共 43 条
  • [1] Synthesis, in vitro antimicrobial and in vivo antitumor evaluation of novel pyrimidoquinolines and its nucleoside derivatives
    Abbas, Hebat-Allah S.
    Hafez, Hend N.
    El-Gazzar, Abdel-Rahman B. A.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (01) : 21 - 30
  • [2] Antioxidant Properties of Synthesized Bicyclic Thiazolopyrimidine Derivatives as Possible Therapeutic Agents
    Ackova, Darinka Gjorgieva
    Kotur-Stevuljevic, Jelena
    Mishra, Chandra Bhushan
    Luthra, Pratibha Mehta
    Saso, Luciano
    [J]. APPLIED SCIENCES-BASEL, 2019, 9 (01):
  • [3] Substituted thiazoles V. Synthesis and antitumor activity of novel thiazolo[2,3-b]quinazoline and pyrido[4,3-d]thiazolo[3,2-a]pyrimidine analogues
    Al-Omary, Fatmah A. M.
    Hassan, Ghada S.
    El-Messery, Shahenda M.
    El-Subbagh, Hussein I.
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 47 : 65 - 72
  • [4] New thiazolopyrimidine as anticancer agents: Synthesis, biological evaluation, DNA binding, molecular modeling and ADMET study
    Al-Rashood, Sara T.
    Elshahawy, Shymaa S.
    El-Qaias, Asmaa M.
    El-Behedy, Dina S.
    Hassanin, Alshaimaa A.
    El-Sayed, Selwan M.
    El-Messery, Shahenda M.
    Shaldam, Moataz A.
    Hassan, Ghada S.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2020, 30 (23)
  • [5] Synthesis, and analgesic and antiparkinsonian activities of thiopyrimidine, pyrane, pyrazoline, and thiazolopyrimidine derivatives from 2-chloro-6-ethoxy-4-acetylpyridine
    Amr, Abd El-Galil E.
    Maigali, Soher S.
    Abdulla, Mohamed M.
    [J]. MONATSHEFTE FUR CHEMIE, 2008, 139 (11): : 1409 - 1415
  • [6] [Anonymous], 2003, The Chemistry of Heterocycles: Structures, Reactions, Synthesis, and Applications
  • [7] Design, synthesis, biological evaluation and in silico molecular docking studies of novel benzochromeno[2,3-d]thiazolopyrimidine derivatives
    Banoth, Sonyanaik
    Boda, Sakram
    Perugu, Shyam
    Balabadra, Saikrishna
    Manga, Vijjulatha
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (03) : 1833 - 1846
  • [8] Synthesis and Cytotoxic Activity of New Thiazolopyrimidine Sugar Hydrazones and Their Derived Acyclic Nucleoside Analogues
    Basiony, Ebtesam A.
    Hassan, Allam A.
    Al-Amshany, Zahra M.
    Abd-Rabou, Ahmed A.
    Abdel-Rahman, Adel A. -H.
    Hassan, Nasser A.
    El-Sayed, Wael A.
    [J]. MOLECULES, 2020, 25 (02):
  • [9] Synthesis, molecular docking and biological evaluation of new thiazolopyrimidine carboxylates as potential antidiabetic and antibacterial agents
    Batool, Iram
    Saeed, Aamer
    Qureshi, Irfan Zia
    Kalsoom, Saima
    Razzaq, Ayesha
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (02) : 1139 - 1163
  • [10] 4-ARYLDIHYDROPYRIDINES, A NEW CLASS OF HIGHLY-ACTIVE CALCIUM-ANTAGONISTS
    BOSSERT, F
    MEYER, H
    WEHINGER, E
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1981, 20 (09): : 762 - 769