'On-solvent' new domino reaction of salicylaldehyde, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-one: fast and efficient approach to medicinally relevant 4-pyridinyl-2-amino-4H-chromene scaffold

被引:21
作者
Elinson, Michail N. [1 ]
Ryzhkov, Fedor V. [1 ]
Vereshchagin, Anatoly N. [1 ]
Korshunov, Alexander D. [1 ]
Novikov, Roman A. [1 ]
Egorov, Mikhail P. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, Moscow 119991, Russia
基金
俄罗斯科学基金会;
关键词
HYBRID MOLECULAR-SYSTEMS; 2-AMINO-4H-CHROMENE SCAFFOLD; URIDINE; WATER; PASE; POT; CYANOACETATES; NUCLEOTIDES; SUSPENSION; DISCOVERY;
D O I
10.1016/j.mencom.2017.11.006
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Sodium acetate catalyzed assembling of salicylaldehydes, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-one in small amount of ethanol gives rapidly (5 min) substituted 4-pyridinyl-2-amino-4H-chromenes in 82-99% yields. This novel domino reaction opens the fast, facile, and flexible way to the new type of functionalized 2-amino-4H-chromene scaffold containing uracil-like moiety, which are relevant compounds for diverse biomedical applications.
引用
收藏
页码:559 / 561
页数:3
相关论文
共 42 条
  • [1] Challenges in the development of organic and hybrid molecular systems
    Ananikov, Valentine P.
    Galkin, Konstantin I.
    Egorov, Mikhail P.
    Sakharov, Alexey M.
    Zlotin, Sergei G.
    Redina, Elena A.
    Isaeva, Vera I.
    Kustov, Leonid M.
    Gening, Marina L.
    Nifantiev, Nikolay E.
    [J]. MENDELEEV COMMUNICATIONS, 2016, 26 (05) : 365 - 374
  • [2] Organic and hybrid molecular systems
    Ananikov, Valentine P.
    Khokhlova, Elena A.
    Egorov, Mikhail P.
    Sakharov, Alexey M.
    Zlotin, Sergei G.
    Kucherov, Alexei V.
    Kustov, Leonid M.
    Gening, Marina L.
    Nifantiev, Nikolay E.
    [J]. MENDELEEV COMMUNICATIONS, 2015, 25 (02) : 75 - 82
  • [3] Anastas P., 1998, GREEN CHEM THEORY PR
  • [4] 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
  • [5] Cai S.-X., 2008, Pat. Appl., Patent No. [WO 2008/5572, 20085572]
  • [6] URIDINE DIPHOSPHATE GLUCOSE - THE COENZYME OF THE GALACTOSE GLUCOSE PHOSPHATE ISOMERIZATION
    CARDINI, CE
    PALADINI, AC
    CAPUTTO, R
    LELOIR, LF
    [J]. NATURE, 1950, 165 (4188) : 192 - 192
  • [7] Uridine protects cortical neurons from glucose deprivation-induced death: Possible role of uridine phosphorylase
    Choi, Ji Woong
    Shin, Chan Young
    Choi, Min Sik
    Yoon, Seo Young
    Ryu, Jong Hoon
    Lee, Jae-Chul
    Kim, Won-Ki
    El Kouni, Mahmoud H.
    Ko, Kwang Ho
    [J]. JOURNAL OF NEUROTRAUMA, 2008, 25 (06) : 695 - 707
  • [8] Combining pot, atom and step economy (PASE) in organic synthesis. Synthesis of tetrahydropyran-4-ones
    Clarke, Paul A.
    Santos, Soraia
    Martin, William H. C.
    [J]. GREEN CHEMISTRY, 2007, 9 (05) : 438 - 440
  • [9] Collard J., 2013, Patent, Patent No. [WO 2013/36403 Al, 2013/36403]
  • [10] ACTION OF PURINE AND PYRIMIDINE NUCLEOTIDES ON THE RAT SUPERIOR CERVICAL-GANGLION
    CONNOLLY, GP
    HARRISON, PJ
    STONE, TW
    [J]. BRITISH JOURNAL OF PHARMACOLOGY, 1993, 110 (04) : 1297 - 1304