An efficient synthesis of novel coumarinyldihydropyrimidin-2-thiones via coumarinylenones

被引:1
|
作者
Tyagi, Abhilash [1 ]
Mahiya, Kuldeep [1 ,2 ]
Kumar, Rajesh [3 ,5 ]
Singh, Sukhdev [1 ,4 ,6 ]
机构
[1] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi, India
[2] FGM Govt Coll, Dept Chem, Adampur Hisar, Haryana, India
[3] BRA Bihar Univ, RDS Coll, PG Dept Chem, Muzaffarpur, Bihar, India
[4] GSSS Hizrawan Khurd 3371, Directorate Secondary Educ, Fatehabad, Haryana, India
[5] BRA Bihar Univ, RDS Coll, PG Dept Chem, Muzaffarpur 842002, Bihar, India
[6] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 110007, India
关键词
4-formylcoumarin; Lewis acid catalyst; coumarinyl-DHPM; Knoevenagel condensation; 2-thioxo-3,4-dihydropyrimidine; CALCIUM-CHANNEL BLOCKERS; ONE-STEP SYNTHESIS; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; BIOLOGICAL EVALUATION; DERIVATIVES; DIHYDROPYRIMIDINES; INHIBITORS; ACETYLCHOLINESTERASE; ANTIBACTERIAL;
D O I
10.1080/00397911.2023.2280576
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The novel coumarinyldihydropyrimidin-2-thiones (coumarinyl-DHPM) have been synthesized by Knoevenagel condensation of 4-formylcoumarins with different beta-keto esters in the presence of aluminum chloride (AlCl3) as Lewis acid catalyst leading to coumarinylenones followed by cyclization with protected thiourea and subsequent deprotection of protected sulfur intermediate by trifluoroacetic acid. The structures of coumarinylenones, protected intermediate and the desired coumarinyl-DHPM were confirmed by their NMR and X-ray diffraction analysis. [GRAPHICS]
引用
收藏
页码:41 / 49
页数:9
相关论文
共 50 条
  • [21] Chemical Synthesis of Some Novel 6-Aminouracil-2-Thiones and Their Glycoside Analogues
    Gaafar, A. M.
    Aly, A. S.
    Abu-Zied, Khadiga M.
    Abdel-Rahman, Asmaa E.
    Helmy, M. M.
    EGYPTIAN JOURNAL OF CHEMISTRY, 2016, 59 (05): : 779 - 797
  • [22] Sonicated chemical synthesis for energy efficient production of Hexahydro-IH-quinazolin-2-thiones
    Saxena, Nisha
    Anjali, Anupama
    Srivastva, Abhay Nanda
    Srivastava, Noopur
    Middha, Riya
    MATERIALS TODAY-PROCEEDINGS, 2022, 60 : 1175 - 1178
  • [23] Synthesis of isoxazolyl triazinan-2-thiones and oxadiazine-4-thiones
    Rajanarendar, E.
    Rao, E. Kalyan
    Reddy, A. Siva Rarni
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2008, 17 (04) : 311 - 314
  • [24] SYNTHESIS OF ISOMERIC 4-HYDROXYLAMINOTHIAZOLIDINE-2-THIONES AND 5-HYDROXYLAMINOTHIAZOLIDINE-2-THIONES
    ORLOVA, TI
    EPSHTEIN, SP
    TASHCHI, VP
    RUKASOV, AF
    BOGELFER, LY
    PUTSYKIN, YG
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1986, (04): : 549 - 553
  • [25] SYNTHESIS OF NOVEL 3,6-DIARYLTETRAHYDRO-2H-1,3-OXAZINE-2-THIONES
    SINGH, S
    SINGH, A
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1994, 33 (05): : 465 - 467
  • [26] An efficient Bronsted acid ionic liquid catalyzed synthesis of novel spiro1,2,4-triazolidine-5-thiones and their photoluminescence study
    Shinde, Vikas B.
    Mhaldar, Pradeep M.
    Chhowala, Tarulata N.
    Mirzaei, Mahmoud
    Ghotekar, Suresh K.
    Rashinkar, Gajanan S.
    Pore, Dattaprasad M.
    JOURNAL OF MOLECULAR STRUCTURE, 2022, 1249
  • [27] NOVEL AND EFFICIENT SYNTHESIS OF ROTENOIDS VIA INTRAMOLECULAR RADICAL ARYLATION
    AHMADJUNAN, SA
    AMOS, PC
    WHITING, DA
    JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (05): : 539 - 545
  • [28] Synthesis of polysubstituted furans via a novel and efficient heterocyclization approach
    Damavandi, Saman
    Sandaroos, Reza
    Pashirzad, Maral
    RESEARCH ON CHEMICAL INTERMEDIATES, 2012, 38 (08) : 1969 - 1974
  • [29] Synthesis of polysubstituted furans via a novel and efficient heterocyclization approach
    Saman Damavandi
    Reza Sandaroos
    Maral Pashirzad
    Research on Chemical Intermediates, 2012, 38 : 1969 - 1974
  • [30] Efficient synthesis of polysubstituted isochromanones via a novel photochemical rearrangement
    Xia, Wujiong
    Shao, Yutian
    Gui, Weijun
    Yang, Chao
    CHEMICAL COMMUNICATIONS, 2011, 47 (39) : 11098 - 11100