SYNTHESIS, REACTIONS, AND CHARACTERIZATION OF 6-AMINO-4-(BENZO[b]THIOPHEN-2-YL)-2-THIOXO-1, 2-DIHYDROPYRIDINE-3,5-DICARBONITRILE

被引:3
|
作者
Abdel-Fattah, Azza M. [1 ]
Attaby, Fawzy A. [1 ]
机构
[1] Cairo Univ, Fac Sci, Dept Chem, Giza 12613, Egypt
关键词
3-(Benzo[b]thiophen-2-yl)-2-cyanoprop-2-enethioamide; 2-cyanoethanethioamide; thieno[2,3-b]pyridine and pyrazolo[3,4-b]pyridine; HETEROCYCLIC SYNTHESIS; ANTI-ALZHEIMER; ANTI-COX-2; ACTIVITIES; DERIVATIVES; PYRIDINE-2(1H)-THIONE; POTENT;
D O I
10.1080/10426507.2011.590562
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Benzothiophene -2- carbaldehyde 1 reacted with 2-cyanoethanethioamide 2 in 1:2 molar ratios to give the corresponding 6-amino-4-(benzo[b]thiophen-2-yl)-2-thioxo-1, 2-dihydropyridine-3,5-dicarbonitrile 6. The synthetic potentiality of compound 6 was investigated via its reaction with active halogen-containing reagents to afford the corresponding thieno[2,3-b]pyridine derivatives 11a,b, 14, 16, and 19. Also, compound 6 reacted with hydrazine hydrate to give the pyrazolo[3,4-b]pyridine derivative 21. Compound 21 condensed with 4-(2-thienyl)benzaldehyde to afford pyrazolo[3,4-b]pyridine derivative 23. Structural elucidation of all the newly synthesized heterocyclic compounds was based on elemental analyses, IR, H-1 NMR, and mass spectra.
引用
收藏
页码:555 / 563
页数:9
相关论文
共 50 条
  • [1] 6-Amino-4-(methylsulfanyl)-2-oxo-1-tolyl-1,2-dihydropyridine-3,5-dicarbonitrile
    Elgemeie, GH
    Jones, PG
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O2107 - O2109
  • [2] 6-amino-4-(4-chlorophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile ethanol solvate
    Jia, Runhong
    Tu, ShuJiang
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O1578 - U3063
  • [3] Synthesis of Novel Fused Heterocycles Based on 6-Amino-4-phenyl-2-thioxo-1,2-dihydropyridine-3,5-dicarbonitrile
    Abdel-Ghany, H.
    El-Sayed, A. M.
    Amer, A. A.
    Ahmed, A. M.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (06) : 2013 - 2019
  • [4] Crystal structure and Hirshfeld surface analysis of 1,6-diamino-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3,5-dicarbonitrile
    Naghiyev, Farid N.
    Khrustalev, Victor N.
    Akkurt, Mehmet
    Khalilov, Ali N.
    Bhattarai, Ajaya
    Kerimli, Fuad Sh.
    Mamedov, Ibrahim G.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2023, 79 : 494 - +
  • [5] 6-Amino-4-(3-nitrophenyl)-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile ethanol solvate
    Xu, Jia-Ning
    Jia, Run-Hong
    Tu, Shu-Jiang
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2007, 63 : O3342 - U4673
  • [6] Synthesis and Aminomethylation of 6-Amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile Morpholinium Salt
    A. O. Kurskova
    V. V. Dotsenko
    K. A. Frolov
    N. A. Aksenov
    I. V. Aksenova
    B. S. Krivokolysko
    S. G. Krivokolysko
    Russian Journal of General Chemistry, 2021, 91 : 1471 - 1483
  • [7] Synthesis and Aminomethylation of 6-Amino-2-(dicyanomethylene)-4-phenyl-1,2-dihydropyridine-3,5-dicarbonitrile Morpholinium Salt
    Kurskova, A. O.
    Dotsenko, V. V.
    Frolov, K. A.
    Aksenov, N. A.
    Aksenova, I., V
    Krivokolysko, B. S.
    Krivokolysko, S. G.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2021, 91 (08) : 1471 - 1483
  • [8] Crystal structure and Hirshfeld surface analysis of 2-amino-6-[(1-phenylethyl)amino]-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile
    Naghiyev, Farid N.
    Khrustalev, Victor N.
    Asadov, Khammed A.
    Akkurt, Mehmet
    Khalilov, Ali N.
    Bhattarai, Ajaya
    Mamedov, Ibrahim G.
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2023, 79 : 526 - +
  • [9] 2-amino-6-ethoxy-4-methylpyridine-3,5-dicarbonitrile
    Mamat, Constantin
    Schulz, Axel
    Villinger, Alexander
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2007, 63 : O4936 - U7217
  • [10] 2-Amino-6-(pyrrolidin-1-yl)-4-p-tolylpyridine-3,5-dicarbonitrile
    Inglebert, S. Antony
    Kamalraja, Jayabal
    Vasuki, Gnanasambandam
    Sethusankar, K.
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1972 - U2403