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
来源：
POLYCYCLIC AROMATIC COMPOUNDS | 2020年 / 40卷 / 01期
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
  • [21] 2,4-Diamino-5-(nitromethyl)-5H-chromeno[2,3-b]pyridine-3-carbonitrile
    Ryzhkova, Yuliya E.
    Ryzhkov, Fedor, V
    Maslov, Oleg, I
    Elinson, Michail N.
    MOLBANK, 2022, 2022 (02)
  • [22] Electrocatalytic Fast and Efficient Multicomponent Approach to Medicinally Relevant Pyrano[3,2-c]quinolone Scaffold
    Elinson, M. N.
    Nasybullin, R. F.
    Nikishin, G. I.
    JOURNAL OF THE ELECTROCHEMICAL SOCIETY, 2013, 160 (07) : G3053 - G3057
  • [23] A facile and efficient multicomponent approach to 5-[5-hydroxy-3-(trifluoromethyl)-1H-pyrazol-4-yl]-5H-chromeno [2,3-b]pyridines
    Elinson, Michail N.
    Vereshchagin, Anatoly N.
    Anisina, Yuliya E.
    Fakhrutdinov, Artem N.
    Goloveshkin, Alexander S.
    Egorov, Mikhail P.
    JOURNAL OF FLUORINE CHEMISTRY, 2018, 213 : 31 - 36
  • [24] Discovery of 2-aryl-5H-chromeno[2,3-b]pyridines (azaxanthenes) as selective glucocorticoid receptor modulators
    Gong, Hua
    Weinstein, David S.
    Doweyko, Arthur M.
    Wang, Jinhong
    Cunningham, Mark
    Holloway, Deborah
    Habte, Sium
    Burke, Christine
    Shuster, David
    Saltercid, Luisa
    Gao, Ling
    Carman, Julie
    Dodd, John
    Somerville, John E.
    Nadler, Steven G.
    Barrish, Joel C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2011, 242
  • [25] Versatile and Sustainable Approach to Access Biologically Relevant Chromeno[2,3-b]pyridine and Benzylpyrazolyl Coumarin Derivatives Using Graphitic Carbon Nitride as a Reusable Heterogeneous Catalyst
    Gajurel, Sushmita
    Sarkar, Rajib
    Sarkar, Fillip Kumar
    Kyndiah, Lenida
    Pal, Amarta Kumar
    ACS OMEGA, 2022, 7 (51): : 48087 - 48099
  • [26] Electrocatalytic Fast and Efficient Multicomponent Approach to Medicinally Relevant (2-Amino-4H-chromen-4-yl) phosphonate Scaffold
    Elinson, Michail N.
    Nasybullin, Ruslan F.
    Nikishin, Gennady I.
    HETEROATOM CHEMISTRY, 2013, 24 (05) : 398 - 403
  • [27] Multicomponent assembling of salicylaldehydes, malononitrile and cyanoacetamides: A simple and efficient approach to medicinally relevant 2-amino-4H-chromene scaffold
    Elinson, Michail N.
    Ryzhkov, Fedor V.
    Vereshchagin, Anatoly N.
    Gorbunov, Sergey V.
    Egorov, Mikhail P.
    COMPTES RENDUS CHIMIE, 2015, 18 (05) : 540 - 546
  • [28] Green synthesis and biological activities assessment of some new chromeno[2,3-b]pyridine derivatives
    Azarifar, Davood
    Ghaemi, Masoumeh
    Jaymand, Mehdi
    Karamian, Roya
    Asadbegy, Mostafa
    Ghasemlou, Fatemeh
    MOLECULAR DIVERSITY, 2022, 26 (02) : 891 - 902
  • [29] Green synthesis and biological activities assessment of some new chromeno[2,3-b]pyridine derivatives
    Davood Azarifar
    Masoumeh Ghaemi
    Mehdi Jaymand
    Roya Karamian
    Mostafa Asadbegy
    Fatemeh Ghasemlou
    Molecular Diversity, 2022, 26 : 891 - 902
  • [30] A Review on the Syntheses and Applications of the 5H-chromeno [2,3-b]pyridines
    Ramazani, Ali
    Kiani, Mohammad Taghi
    Rezayati, Sobhan
    LETTERS IN ORGANIC CHEMISTRY, 2023, 20 (01) : 28 - 53
12345