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
来源：
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS | 2012年 / 187卷 / 05期
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
  • [41] Design, synthesis and biological evaluation of novel (E)-2-benzylidene-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl) hydrazine-1-carboxamide derivatives as α-glucosidase inhibitors
    Zhang, Jin-He
    Xie, Hong-Xu
    Li, Yue
    Wang, Kai-Ming
    Song, Zhiling
    Zhu, Kong-Kai
    Fang, Lei
    Zhang, Juan
    Jiang, Cheng-Shi
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2021, 52
  • [42] GREEN SYNTHESIS OF 2-BENZOYL-6-HYDROXY-3-METHYL-5-(2-SUBSTITUTED-2,3-DIHYDRO-1H-1,5-BENZODIAZEPIN-4-YL) BENZO [b] FURANS AND 2-BENZOYL-6-HYDROXY-3-METHYL-5-(2-SUBSTITUTED-2,3-DIHYDRO-1H-1,5-BENZOTHIAZEPIN-4-YL) BENZO [b] FURANS AND THEIR ANTIMICROBIAL ACTIVITY
    Sarasija, M.
    Sudershan, K.
    Ashok, D.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 24 (02) : 199 - 204
  • [43] An Efficient and Facile Synthesis of 5-(Thiophene-2-carbonyl)-6-(trifluoromethyl)-tetrahydro-pyrimidin-2(1H)-one and 6-(Thiophen-2-yl)-4,5-dihydropyrimidin-2(1H)-one from Same Substrates Under Different Conditions
    Rong Liang-Ce
    Zha, Yunyun
    Xia, Sheng
    Ji, Linlin
    Zhang, Jing
    Cai, Peijun
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2016, 53 (01) : 56 - 63
  • [44] Novel Synthesis and Antitumor Evaluation of Polyfunctionally Substituted Heterocyclic Compounds Derived from 2-Cyano-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-acetamide
    Shams, Hoda Z.
    Mohareb, Rafat M.
    Helal, Maher H.
    Mahmoud, Amira E.
    MOLECULES, 2011, 16 (01) : 52 - 73
  • [45] The irony of chirality - unveiling the distinct mechanistic binding and activities of 1-(3-(4-amino-5-(7-methoxy-5-methylbenzo[b]thiophen-2-yl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)pyrrolidin-1-yl)prop-2-en-1-one enantiomers as irreversible covalent FGFR4 inhibitors
    Akher, Farideh Badichi
    Farrokhzadeh, Abdolkarim
    Olotu, Fisayo A.
    Agoni, Clement
    Soliman, Mahmoud E. S.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (05) : 1176 - 1190
  • [46] Synthesis, spectral characterization (FT-IR, NMR, XRD) and computational studies of chloroacetyl chloride incorporated 3t-butyl-2r,6c-diphenyl/di(thiophen-2-yl)piperidin-4-ones
    Doss, M. Arockia
    Rajarajan, G.
    Dhineshkumar, E.
    Amala, S.
    Thanikachalam, V
    Selvanayagam, S.
    Sridhar, B.
    JOURNAL OF MOLECULAR STRUCTURE, 2020, 1200
  • [47] Synthesis of new 2-(5-(4-alkyl-4H-dithieno[3,2-b:2′,3′-d]pyrrol-2-yl)thiophen-2-yl)methylene)malononitrile: Dopant free hole transporting materials for perovskite solar cells with high power conversion efficiency
    Bharath, Dyaga
    Sasikumar, M.
    Chereddy, Narendra Reddy
    Vaidya, Jayathirtha Rao
    Pola, Someshwar
    SOLAR ENERGY, 2018, 174 : 130 - 138
  • [48] Design and Synthesis of Novel Heterocycles Utilizing 4,6-Dimethyl-1-((4-methylthiazol-2-yl)amino)-2-oxo-1,2-dihydropyridine-3-carbonitrile
    Borik, Rita M.
    LETTERS IN ORGANIC CHEMISTRY, 2024, 21 (11) : 973 - 982
  • [49] Divergent Synthesis of (Benzo[b][1,4]diazepin-2-yl)phosphonates and (Quinoxalin-2-yl)methylphosphonates from Phosphoryl-Substituted Conjugated Ynones
    Mitrofanov, Alexander Yu.
    Gontcharenko, Victoria E.
    Beletskaya, Irina P.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2024, 27 (04)
  • [50] Design, synthesis and biological evaluation of aryl 1,3-oxazo-le-oxazolo[4,5-b]pyridin-2-yl)benzo[d]thiazol-6-yl)thiazole-2-car-boxamides as anticancer agents
    Bairi, Suresh
    Alagarsamy, Veerachamy
    Rachamalla, Shaym Sunder
    CHEMICAL DATA COLLECTIONS, 2022, 40
12345