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
  • [21] Synthesis of novel spiro[benzo[4,5]thiazolo[3,2-a]chromeno[2,3-d] pyrimidine-14,3′-indoline]-1,2′,13(2H)-triones via three component reaction
    Jannati, Saeideh
    Esmaeili, Abbas Ali
    [J]. TETRAHEDRON, 2018, 74 (24) : 2967 - 2972
  • [22] Joule J.A., 2000, HETEROCYCLIC CHEM, V4th
  • [23] Katritzky A.R., 2008, COMPREHENSIVE HETERO, V1st, DOI [10.1016/B978-008044992-0.00404-1, DOI 10.1016/B978-008044992-0.00404-1]
  • [24] Development of Novel Thiazolopyrimidines as CDC25B Phosphatase Inhibitors
    Kolb, Stephanie
    Mondesert, Odile
    Goddard, Mary-Lorene
    Jullien, Denis
    Villoutreix, Bruno O.
    Ducommun, Bernard
    Garbay, Christiane
    Braud, Emmanuelle
    [J]. CHEMMEDCHEM, 2009, 4 (04) : 633 - 648
  • [25] Design and synthesis of 2,4-disubstituted polyhydroquinolines as prospective antihyperglycemic and lipid modulating agents
    Kumar, Atul
    Sharma, Siddharth
    Tripathi, Vishwa Deepak
    Maurya, Ram Awatar
    Srivastava, Swayam Prakash
    Bhatia, Gitika
    Tamrakar, A. K.
    Srivastava, Arvind Kumar
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (11) : 4138 - 4148
  • [26] Design, synthesis, and biological evaluation of 7H-thiazolo[3,2-b]-1,2,4-triazin-7-one derivatives as novel acetylcholinesterase inhibitors
    Liu, Si-jie
    Yang, Liu
    Jin, Zhe
    Huang, Er-fang
    Wan, David Chi Cheong
    Lin, Huang-quan
    Hu, Chun
    [J]. ARKIVOC, 2009, : 333 - 348
  • [27] Love B., 1974, J MED CHEM, V19, P956, DOI [DOI 10.1021/JM00255A010, 10.1021/jm00255a010]
  • [28] Synthesis and Biological Studies of Novel Biphenyl-3,5-dihydro-2H-thiazolopyrimidines Derivatives
    Maddila, S.
    Damu, G. L. V.
    Oseghe, E. O.
    Abafe, O. A.
    Rao, C. Venakata
    Lavanya, P.
    [J]. JOURNAL OF THE KOREAN CHEMICAL SOCIETY-DAEHAN HWAHAK HOE JEE, 2012, 56 (03): : 334 - 340
  • [29] Synthesis, Crystal Structure, and Biological Evaluation of Fused Thiazolo[3,2-a]Pyrimidines as New Acetylcholinesterase Inhibitors
    Mahgoub, Mohamed Y.
    Elmaghraby, Awatef M.
    Harb, Abd-Elfttah A.
    Ferreira da Silva, Joao L.
    Justino, Goncalo C.
    Matilde Marques, M.
    [J]. MOLECULES, 2019, 24 (12):
  • [30] Tacripyrines, the First Tacrine-Dihydropyridine Hybrids, as Multitarget-Directed Ligands for the Treatment of Alzheimer's Disease
    Marco-Contelles, Jose
    Leon, Rafael
    de los Rios, Cristobal
    Samadi, Abdelouahid
    Bartolini, Manuela
    Andrisano, Vincenza
    Huertas, Oscar
    Barril, Xavier
    Javier Luque, F.
    Rodriguez-Franco, Maria I.
    Lopez, Beatriz
    Lopez, Manuela G.
    Garcia, Antonio G.
    do Carmo Carreiras, Maria
    Villarroya, Mercedes
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (09) : 2724 - 2732