An expeditious synthesis of novel pyranopyridine derivatives involving chromenes under controlled microwave irradiation

被引:87
作者
Raghuvanshi, Dushyant Singh [1 ]
Singh, Krishna Nand [1 ]
机构
[1] Banaras Hindu Univ, Fac Sci, Dept Chem, Varanasi 221005, Uttar Pradesh, India
关键词
Friedlander annulation; pyranopyridines; microwave synthesis; multi-component reaction; 2-amino-3-cyano-4H-chromenes; NAD(+)-DEPENDENT DNA-LIGASE; THROUGHPUT SCREENING ASSAY; MULTICOMPONENT REACTIONS; BIOLOGICAL EVALUATION; ASSISTED SYNTHESIS; IN-VITRO; INHIBITION; QUINOLINES; DISCOVERY; APOPTOSIS;
D O I
10.3998/ark.5550190.0011.a25
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of novel pyrano[2,3-b] pyridine derivatives has been achieved by the cyclocondensation of 2-amino-3-cyano-4H-chromenes and cyclohexanone in the presence of aluminium chloride under controlled microwave irradiation. The experimental conditions have been thoroughly optimized and established, allowing significant rate enhancements and excellent yields. The starting 4H-chromenes were obtained using one pot DBU-catalysed microwave induced multicomponent condensation of resorcinol, malononitrile and aromatic aldehydes.
引用
收藏
页码:305 / 317
页数:13
相关论文
共 70 条
  • [1] FLINDERSINE FROM FAGARA-HEITZII
    AHMAD, S
    [J]. JOURNAL OF NATURAL PRODUCTS, 1984, 47 (02): : 391 - 392
  • [2] Aminocyanopyridine inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
    Anderson, DR
    Hegde, S
    Reinhard, E
    Gomez, L
    Vernier, WF
    Lee, L
    Liu, S
    Sambandam, A
    Snider, PA
    Masih, L
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2005, 15 (06) : 1587 - 1590
  • [3] [Anonymous], 1997, COUMARINS BIOL APPL
  • [4] Cancer chemopreventive effect of phenothiazines and related tri-heterocyclic analogues in the 12-O-tetradecanoylphorbol-13-acetate promoted Epstein-Barr virus early antigen activation and the mouse skin two-stage carcinogenesis models
    Azuine, MA
    Tokuda, H
    Takayasu, J
    Enjyo, F
    Mukainaka, T
    Konoshima, T
    Nishino, H
    Kapadia, GJ
    [J]. PHARMACOLOGICAL RESEARCH, 2004, 49 (02) : 161 - 169
  • [5] Three-component process for the synthesis of 2-amino-2-chromenes in aqueous media
    Ballini, R
    Bosica, G
    Conforti, ML
    Maggi, R
    Mazzacani, A
    Righi, P
    Sartori, G
    [J]. TETRAHEDRON, 2001, 57 (07) : 1395 - 1398
  • [6] Simple coumarins and analogues in medicinal chemistry: Occurrence, synthesis and biological activity
    Borges, F
    Roleira, F
    Milhazes, N
    Santana, L
    Uriarte, E
    [J]. CURRENT MEDICINAL CHEMISTRY, 2005, 12 (08) : 887 - 916
  • [7] Specific and potent inhibition of NAD+-dependent DNA ligase by pyridochromanones
    Brötz-Oesterhelt, H
    Knezevic, I
    Bartel, S
    Lampe, T
    Warnecke-Eberz, U
    Ziegelbauer, K
    Häbich, D
    Labischinski, H
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (41) : 39435 - 39442
  • [8] Microwave enhanced synthesis
    Caddick, Stephen
    Fitzmaurice, Richard
    [J]. TETRAHEDRON, 2009, 65 (17) : 3325 - 3355
  • [9] Synthesis and in vitro selective anti-Helicobacter pylori activity of N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides
    Chimenti, F
    Bizzarri, B
    Bolasco, A
    Secci, D
    Chimenti, P
    Carradori, S
    Granese, A
    Rivanera, D
    Lilli, D
    Scaltrito, MM
    Brenciaglia, MI
    [J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2006, 41 (02) : 208 - 212
  • [10] Synthesis of quinolines via ruthenium-catalysed amine exchange reaction between anilines and trialkylamines
    Cho, CS
    Oh, BH
    Kim, JS
    Kim, TJ
    Shim, SC
    [J]. CHEMICAL COMMUNICATIONS, 2000, (19) : 1885 - 1886