Multicomponent transformation of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile, and pyrazolin-5-ones into substituted 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles

被引:8
作者
Elinson, M. N. [1 ]
Vereshchagin, A. N. [1 ]
Anisina, Y. E. [1 ]
Goloveshkin, A. S. [2 ]
Ushakov, I. E. [2 ]
Egorov, M. P. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia
[2] Russian Acad Sci, AN Nesmeyanov Inst Organoelement Cpds, 28 Ul Vavilova, Moscow 119991, Russia
基金
俄罗斯基础研究基金会;
关键词
multicomponent reactions; catalysis; salicylaldehydes; 2-aminoprop-1-ene-1-1,3-tricarbonitrile; 2-pyrazolin-5-ones; cyclization; chromeno[2,3-b]pyridines; EFFICIENT APPROACH; SOLVENT-FREE; MEDICINALLY RELEVANT; ON-SOLVENT; MALONONITRILE; POT; MOLECULES; DESIGN; WATER; ALDEHYDES;
D O I
10.1007/s11172-018-2278-1
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new multicomponent reaction, namely, a one-pot transformation of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile, and 2-pyrazolin-5-ones in the presence of triethylamine as the catalyst in a minimum amount of propanol leads to the previously unknown substituted 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-5H-chromeno [2,3-b]-pyridine-3-carbonitriles in 63-98% yields. This reaction provides a facile and efficient route to a new type of functionalized 5-C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine systems containing the 2-pyrazolin-5-one moiety. These reaction products are promising compounds for different biomedical applications.
引用
收藏
页码:1695 / 1703
页数:9
相关论文
共 43 条
  • [1] 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
  • [2] [Anonymous], TOPAS 4 2 US MAN
  • [3] [Anonymous], PYRAZOLES AS DRUGS
  • [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] An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles
    Baumann, Marcus
    Baxendale, Ian R.
    [J]. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2265 - 2319
  • [6] Solvent-assisted mechanochemistry
    Bowmaker, Graham A.
    [J]. CHEMICAL COMMUNICATIONS, 2013, 49 (04) : 334 - 348
  • [7] Rietveld refinement and structure verification using 'Morse' restraints
    Bushmarinov, Ivan S.
    Dmitrienko, Artem O.
    Korlyukov, Alexander A.
    Antipin, Mikhail Yu.
    [J]. JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2012, 45 : 1187 - 1197
  • [8] Organic synthesis reactions on-water at the organic-liquid water interface
    Butler, Richard N.
    Coyne, Anthony G.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (42) : 9945 - 9960
  • [9] Multicomponent reactions: advanced tools for sustainable organic synthesis
    Cioc, Razvan C.
    Ruijter, Eelco
    Orru, Romano V. A.
    [J]. GREEN CHEMISTRY, 2014, 16 (06) : 2958 - 2975
  • [10] 'On water' Knoevenagel condensation of isatins with malononitrile
    Demchuk, Dmitry V.
    Elinson, Michail N.
    Nikishin, Gennady I.
    [J]. MENDELEEV COMMUNICATIONS, 2011, 21 (04) : 224 - 225