Efficient and Convenient Protocol for the Synthesis of Novel 1,2,4-Triazolo[3,4-b][1,3,4]Thiadiazines

被引：12
|
作者：
Foroughifar, Naser [1 ,2 ]
Mobinikhaledi, Akbar [2 ]
Ebrahimi, Sattar [2 ]
机构：
[1] Islamic Azad Univ, Fac Chem, N Tehran Branch, Tehran, Iran
[2] Arak Univ, Dept Chem, Fac Sci, Arak, Iran
来源：
SYNTHETIC COMMUNICATIONS | 2010年 / 40卷 / 16期
关键词：
Schiff-base; 1; 2; 4-triazole; triazolothiadiazine; ANTIBACTERIAL; DERIVATIVES;
D O I：
10.1080/00397910903261387
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The novel triazolothiadiazine analogs 5a-p were obtained via a multistep synthetic sequence beginning with 5-substituted 4-amino-1,2,4-triazole-3-thiols 1. Compound 1, in reaction with various aromatic aldehydes 2 in acetic acid, afforded Schiff bases 3a-p. Cyclization of 3a-p with ethyl chloroacetate 4 in the presence of sodium hydride at room temperature gave triazolothiadiazines 5a-p in good yields.
引用
收藏
页码：2421 / 2428
页数：8
相关论文
共 50 条
  • [1] A New Approach to the Synthesis of 1,2,4-Triazolo[3,4-b][1,3,4] thiadiazines
    Skryl'nikova, M. A.
    Khramchikhin, A. V.
    Krivchun, M. N.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2017, 87 (06) : 1321 - 1322
  • [2] A new approach to the synthesis of 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines
    M. A. Skryl’nikova
    A. V. Khramchikhin
    M. N. Krivchun
    Russian Journal of General Chemistry, 2017, 87 : 1321 - 1322
  • [3] Antimicrobial and antiinflammatory studies on some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles containing quinoxaline
    Wagle, Shivananda
    Adhikari, Airody Vasudeva
    Kumari, Nalilu Suchetha
    ASIAN JOURNAL OF CHEMISTRY, 2008, 20 (01) : 629 - 641
  • [4] Synthesis and antimicrobial activities of some1,2,4-triazolo [3,4-b] [1,3,4] thiadiazoles and 1,2,4-triazolo [3,4-b] [1,3,4] thiadiazines bearing bistrifluoromethylphenyl moiety
    Bobade, V. D., 1600, Journal of Chemical and Pharmaceutical Research (06):
  • [5] Synthesis, crystal structure and biological evaluation of some novel 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines
    Khan, Imtiaz
    Zaib, Sumera
    Ibrar, Aliya
    Rama, Nasim Hasan
    Simpson, Jim
    Iqbal, Jamshed
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 78 : 167 - 177
  • [6] A CONVENIENT AND NOVEL SYNTHESIS OF 1,2,4-TRIAZOLO[3,4-B][1,3,4]-THIADIAZOLES AS POTENTIAL PESTICIDES
    CHATURVEDI, B
    TIWARI, N
    NIZAMUDDIN
    AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1988, 52 (05): : 1229 - 1232
  • [7] Effective synthesis of 7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines
    Kulikov, Alexander S.
    Epishina, Margarita A.
    Fershtat, Leonid L.
    Makhova, Nina N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2018, 54 (06) : 669 - 672
  • [8] Effective synthesis of 7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines
    Alexander S. Kulikov
    Margarita A. Epishina
    Leonid L. Fershtat
    Nina N. Makhova
    Chemistry of Heterocyclic Compounds, 2018, 54 : 669 - 672
  • [9] Synthesis, antimicrobial and anti-inflammatory activities of some 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazines bearing trichlorophenyl moiety
    Karegoudar, Prakash
    Prasad, D. Jagdeesh
    Ashok, Mithun
    Mahalinga, Manjathuru
    Poojary, Boja
    Holla, Bantwal Shivarama
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2008, 43 (04) : 808 - 815
  • [10] Synthesis and antiviral activity of novel [1,2,4]triazolo[3,4b][1,3,4]thiadiazoles, [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazepines
    Farghaly, Abdel-Rahman
    De Clercq, Erik
    El-Kashef, Hussein
    ARKIVOC, 2006, : 137 - 151
12345