A one-pot, pseudo four-component synthesis of novel benzopyrano[2,3-b]pyridines under solvent-free conditions

被引:20
作者
Olyaei, Abolfazl [1 ]
Vaziri, Mohsen [1 ]
Razeghi, Reza [1 ]
机构
[1] Payame Noor Univ, Dept Chem, Tehran, Iran
关键词
Naphthol; Benzopyranopyridine; Malononitrile; Aldehyde; Knoevenagel condensation; NAD(+)-DEPENDENT DNA-LIGASE; BIS-SCHIFF BASES; CONVENIENT; FLINDERSINE; PRODUCTS; PROTEIN; SYSTEM;
D O I
10.1016/j.tetlet.2013.01.124
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile, one-pot, pseudo four-component catalyst- and solvent-free synthesis of novel benzopyrano[2,3-b]pyridines is achieved by Michael addition of various naphthols to iminocoumarin derivatives obtained from Knoevenagel condensation of salicylaldehydes with malononitrile, which can be attacked by another molecule of malononitrile to afford the title products. The advantages of this procedure are mild reaction conditions, high yields of products, generality, short reaction times and operational simplicity. (C) 2013 Published by Elsevier Ltd.
引用
收藏
页码:1963 / 1966
页数:4
相关论文
共 50 条
  • [41] An efficient one-pot four-component Gewald reaction: Synthesis of substituted 2-aminothiophenes with coumarin-thiazole scaffolds under environmentally benign conditions
    Kavitha, Kotthireddy
    Srikrishna, Devulapally
    Dubey, Pramod Kumar
    Aparna, Pasula
    [J]. JOURNAL OF SULFUR CHEMISTRY, 2019, 40 (02) : 195 - 208
  • [42] One-pot three-component regioselective synthesis of linear naphtho[2,3-b]-furan-4,9-diones
    Teimouri, Mohammad Bagher
    Khavasi, Hamid Reza
    [J]. TETRAHEDRON, 2007, 63 (41) : 10269 - 10275
  • [43] Aspartic acid as a highly efficient and nontoxic organocatalyst for the one-pot synthesis of tri- and tetrasubstituted imidazoles under solvent-free conditions
    Ghorbani-Choghamarani, A.
    Hajjami, M.
    Gholamian, F.
    Azadi, G.
    [J]. RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 51 (03) : 352 - 356
  • [44] One-pot three-component coupling reaction: solvent-free synthesis of novel 3-substituted indoles catalyzed by PMA-SiO2
    Srihari, P.
    Singh, Vinay K.
    Bhunia, Dinesh C.
    Yadav, J. S.
    [J]. TETRAHEDRON LETTERS, 2009, 50 (27) : 3763 - 3766
  • [45] An efficient synthesis of imidazo[2,1-b][1,3]thiazins via a one-pot, three-component and solvent-free reaction
    Ghanbari, Mohammad Mehdi
    [J]. GREEN CHEMISTRY LETTERS AND REVIEWS, 2016, 9 (04) : 203 - 207
  • [46] Efficient One-Pot Four-Component Synthesis and X-ray Crystallographic Structure of 2-Pyridone Derivatives
    Balalaie, Saeed
    Hashemi, Mohammed M.
    Khezri, S. Hadi
    Rominger, Frank
    Ghabraie, Elmira
    Oeser, Thomas
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2013, 50 (06) : 1272 - 1280
  • [47] Silica Sulfuric Acid: An Efficient Heterogeneous Catalyst for the One-Pot Synthesis of 1,4-Dihydropyridines under Mild and Solvent-Free Conditions
    Datta, Bandita
    Pasha, M. Afzal
    [J]. CHINESE JOURNAL OF CATALYSIS, 2011, 32 (07) : 1180 - 1184
  • [48] ONE-POT SYNTHESIS OF 1H-INDAZOLO[2,1-b]PHTHALAZINETRIONE CATALAZED BY MAGNETIC ROOM TEMPERATURE DICATIONIC IONIC LIQUID UNDER SOLVENT-FREE CONDITIONS
    Godajdar, Bijan Mombani
    Kiasat, Ali Reza
    Hashemi, Mohammad Mahmoodi
    [J]. HETEROCYCLES, 2013, 87 (03) : 559 - 570
  • [49] Facile synthesis of Z/E-3-arylmethylidene-2,3-dihydroindol-2-one under solvent-free conditions
    Xu, Tian-Tu
    Wang, Shun-Yi
    Ji, Shun-Jun
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2006, 26 (10) : 1414 - 1417
  • [50] Organocatalytic approach toward the green one-pot synthesis of novel benzo[f]chromenes and 12H-benzo[5,6]chromeno[2,3-b]pyridines
    Olyaei, Abolfazl
    Shahsavari, Mohammad Sadegh
    Sadeghpour, Mahdieh
    [J]. RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (02) : 943 - 956