Efficient Multicomponent Approach to the Medicinally Relevant 5-aryl-chromeno[2,3-b]pyridine Scaffold

被引:18
|
作者
Elinson, Michail N. [1 ]
Vereshchagin, Anatoly N. [1 ]
Anisina, Yuliya E. [1 ]
Egorov, Mikhail P. [1 ]
机构
[1] ND Zelinskii Inst Organ Chem, Leninsky Prospect 47, Moscow 119991, Russia
关键词
2-Aminoprop-1-ene-1; 1; 3-tricarbonitrile; benzaldehyde; catalysis; chromeno[2; 3-b]pyridine; dimedone; multicomponent reaction; NAD(+)-DEPENDENT DNA-LIGASE; ONE-POT SYNTHESIS; 3-COMPONENT SYNTHESIS; ONE-STEP; MALONONITRILE; INHIBITORS; MOLECULES; ALDEHYDES; DESIGN;
D O I
10.1080/10406638.2017.1363062
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The general multicomponent approach was found to the medicinally relevant 5-aryl-chromeno[2,3-b]pyridine scaffold. Triethylamine catalyzed multicomponent reaction of benzaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile and dimedone in a minimal amount of propanol results in efficient formation of substituted 2,4-diamino-8,8-dimethyl-6-oxo-5-aryl-6,7,8,9-tetrahydro-5H-chromeno[2,3-b]pyridine-3-carbonitriles in 75-80% yields. This general and efficient approach avoids traditional recrystallization and chromatographic purification stages and opens a convenient way to scaffolds, promising for many diverse oriented medical applications.
引用
收藏
页码:108 / 115
页数:8
相关论文
共 50 条
  • [41] SYNTHESIS AND PROPERTIES OF 10-ARYL-10-HYDROXY-10H-CHROMENO[2,3-B]PYRIDINES
    MIKHALEV, AI
    KONSHIN, ME
    ZHURNAL ORGANICHESKOI KHIMII, 1977, 13 (05): : 1111 - 1115
  • [42] Cascade assembling of pyrazolin-5-ones and benzylidenemalononitriles: the facile and efficient approach to medicinally relevant spirocyclopropylpyrazolone scaffold
    Vereshchagin, Anatoly N.
    Elinson, Michail N.
    Korshunov, Aleksander D.
    Korolev, Victor A.
    Egorov, Mikhail P.
    HETEROCYCLIC COMMUNICATIONS, 2015, 21 (06) : 355 - 360
  • [43] 5-Bromo-1H-pyrrolo[2,3-b]pyridine
    Starha, Pavel
    Travnicek, Zdenek
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O381 - +
  • [44] A convenient approach to the synthesis of dialkyl 5-oxo-1,2-dihydro-5H-chromeno[4,3-b]pyridine-2,3-dicarboxylates
    Glasnov, Toma N.
    Ivanov, Ivo C.
    SYNTHETIC COMMUNICATIONS, 2008, 38 (10) : 1579 - 1588
  • [45] Synthesis and anti-inflammatory activities of 4H-chromene and chromeno[2,3-b]pyridine derivatives
    Shu-Ting Chung
    Wen-Hsin Huang
    Chih-Kuo Huang
    Feng-Cheng Liu
    Ren-Yeong Huang
    Chin-Chen Wu
    An-Rong Lee
    Research on Chemical Intermediates, 2016, 42 : 1195 - 1215
  • [46] Synthesis and anti-inflammatory activities of 4H-chromene and chromeno[2,3-b]pyridine derivatives
    Chung, Shu-Ting
    Huang, Wen-Hsin
    Huang, Chih-Kuo
    Liu, Feng-Cheng
    Huang, Ren-Yeong
    Wu, Chin-Chen
    Lee, An-Rong
    RESEARCH ON CHEMICAL INTERMEDIATES, 2016, 42 (02) : 1195 - 1215
  • [47] Reactions with pyridinethione derivatives:: Synthesis and characterization of thienyl[2,3-b]pyridine, pyrido[2′,3′:4,5] thieno[2,3-b]pyridazine, pyrido[2′,3′:4,5] thieno[2,3-b]-pyrimidinone, pyrazolino[3′,4′:4,5] thieno[2,3-b]pyridine and aminopyrazolo[3,4-b]pyridine derivatives
    Attaby, FA
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1997, 126 : 27 - 38
  • [48] Synthesis of 2-(1-aryl-1H-tetrazol-5-yl)-thieno[2,3-b]pyridine derivatives
    Koltsov, Nikolai Yu
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (08) : 768 - 772
  • [49] Synthesis of 2-(1-aryl-1H-tetrazol-5-yl)-thieno[2,3-b]pyridine derivatives
    Nikolai Yu. Koltsov
    Chemistry of Heterocyclic Compounds, 2019, 55 : 768 - 772
  • [50] Synthesis of 9,11-diamino-12H-benzo[5,6]-chromeno[2,3-b]pyridine-10-carbonitriles
    V. A. Osyanin
    D. V. Osipov
    Yu. N. Klimochkin
    Chemistry of Heterocyclic Compounds, 2012, 47 : 1460 - 1462