Facile entries for regioselective synthesis of [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones from 2-thiouracil

被引：11
作者：
Shawali, A. S. [1 ]
Abbas, I. M.
Mahran, A. M.
机构：
[1] Cairo Univ, Fac Sci, Dept Chem, Giza, Egypt
[2] Natl Res Ctr, Giza, Egypt
来源：
JOURNAL OF THE IRANIAN CHEMICAL SOCIETY | 2004年 / 1卷 / 01期
关键词：
heterocycles; hydrazones; rearrangement; synthetic methods; 1,2,4-triazolo-pyrimidine;
D O I：
10.1007/BF03245768
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Three new alternative synthetic strategies based on reactions of hydrazonoyl halides 3 with 2-methylthiouracil 2 and treatment of either 2-pyrimidinyl thiohydrazonates 8 or the diazonium coupling products of active (pyrimidin-2-ylthio)methylene compounds 12 with sodium ethoxide in ethanol are described for the title compounds. The mechanisms and regiochemistry of the studied reactions are discussed.
引用
收藏
页码：33 / 39
页数：7
相关论文
共 50 条
  • [1] Facile entries for regioselective synthesis of [1,2,4]triazolo-[4,3-a]pyrimidin-5(1H)-ones from 2-thiouracil
    A. S. Shawali
    I. M. Abbas
    A. M. Mahran
    Journal of the Iranian Chemical Society, 2004, 1 : 33 - 39
  • [2] Retro Diels Alder protocol for regioselective synthesis of novel [1,2,4]triazolo[4,3-a]pyrimidin-7(1H)-ones
    Said, Awad, I
    Palko, Marta
    Haukka, Matti
    Fulop, Ferenc
    RSC ADVANCES, 2020, 10 (56) : 33937 - 33943
  • [3] Synthesis of [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones by the Condensation of 3-Alkylamino-5-amino-1-phenyl[1,2,4]triazoles with β-Keto Esters or Diethyl Ethoxymethylenemalonate
    Astakhov, A. V.
    Zubatyuk, R. I.
    Abagyan, R. S.
    Chernyshev, V. M.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 49 (10) : 1500 - 1507
  • [4] Synthesis of [1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones by the Condensation of 3-Alkylamino-5-amino-1-phenyl[1,2,4]triazoles with β-Keto Esters or Diethyl Ethoxymethylenemalonate
    A. V. Astakhov
    R. I. Zubatyuk
    R. S. Abagyan
    V. M. Chernyshev
    Chemistry of Heterocyclic Compounds, 2014, 49 : 1500 - 1507
  • [5] Synthesis and Antitumor Screening of New 1,7-Diphenyl-3-(1,3-disubstituted-1H-pyrazole-4-carbonyl)-[1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones
    Shawali, Ahmad S.
    Sherif, Sherif M.
    Darwish, Manal A. A.
    El-merzabani, Mahmoud M.
    ARCHIVES OF PHARMACAL RESEARCH, 2010, 33 (01) : 55 - 60
  • [6] A new entry for short and regioselective synthesis of [1,2,4]Triazolo[4,3-b][1,2,4]-triazin-7(1H)-ones
    Shawali, AS
    Gomha, SM
    JOURNAL FUR PRAKTISCHE CHEMIE-PRACTICAL APPLICATIONS AND APPLIED CHEMISTRY, 2000, 342 (06): : 599 - 604
  • [7] Synthesis and Cytotoxicity Evaluation of Some Novel Thiazoles, Thiadiazoles, and Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5(1H)-ones Incorporating Triazole Moiety
    Gomha, Sobhi M.
    Ahmed, Sayed A.
    Abdelhamid, Abdou O.
    MOLECULES, 2015, 20 (01): : 1357 - 1376
  • [8] A facile and practical one-pot synthesis of [1,2,4]-triazolo[4,3-a]pyridines
    Vadagaonkar, Kamlesh S.
    Murugan, Kaliyappan
    Chaskar, Atul C.
    Bhate, Prakash M.
    RSC ADVANCES, 2014, 4 (64): : 34056 - 34064
  • [9] A Facile One-pot Synthesis and Antimicrobial Activity of Pyrido [2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5-ones
    Farghaly, Thoraya A.
    Riyadh, Sayed M.
    Abdallah, Magda A.
    Ramadan, Mohamed A.
    ACTA CHIMICA SLOVENICA, 2011, 58 (01) : 87 - 94
  • [10] Synthesis and Selective Functionalization of [1,2,4]Triazolo[4,3-a]pyrazines
    Demmer, Charles S.
    Jorgensen, Morten
    Kehler, Jan
    Bunch, Lennart
    Rasmussen, Lars K.
    SYNLETT, 2015, 26 (04) : 519 - 524
12345