Isoquinoline-Catalyzed Reaction between 4-Hydroxycoumarin or 4-Hydroxy-6-methylpyran-1-one and Dialkyl Acetylene Dicarboxylates: Synthesis of Coumarin and Pyranopyrane Derivatives

被引:9
|
作者
Anary-Abbasinejad, Mohammad [1 ]
Anaraki-Ardakani, Hossein [1 ]
Mosslemin, Mohammad Hossein [1 ]
Khavasi, Hamid Reza [2 ]
机构
[1] Islamic Azad Univ, Dept Chem, Yazd Branch, Yazd, Iran
[2] Shaheed Beheshti Univ, Dept Chem, Tehran, Iran
关键词
acetylenedicarboxylic esters; isoquinoline; pyranopyran derivatives; coumarin derivatives; ONE-POT SYNTHESIS; DIMETHYL ACETYLENEDICARBOXYLATE; 3-COMPONENT REACTION; HETEROCYCLIC-COMPOUNDS; ADDITION-REACTIONS; FACILE SYNTHESIS; EFFICIENT SYNTHESIS; PHOSPHORUS YLIDES; TRIPHENYLPHOSPHINE; PYRIDINES;
D O I
10.1590/S0103-50532010000200018
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
In this work we report the reaction between dialkyl acetylenedicarboxylates and enolic systems such as 5,5-dimethyl-1,3-cyclohexanedione, 1,3-cyclohexanedione, 4-hydroxycoumarin or 4-hydroxy-6-methylpyran-1-one in the presence of isoquinoline, which leads to new coumarin and pyranopyran derivatives.
引用
收藏
页码:319 / U212
页数:12
相关论文
共 50 条
  • [31] Synthesis of new coumarin[1,3]oxazine derivatives of 7-hydroxy-6-isobornyl-4-methylcoumarin and their antioxidant activity
    Popova, Svetlana A.
    Shevchenko, Oksana G.
    Chukicheva, Irina Yu
    CHEMICAL BIOLOGY & DRUG DESIGN, 2022, 100 (06) : 994 - 1004
  • [32] Synthesis of 2-hydroxy-7-[benzimidazol-2-yl]methyl-5-methylpyrazolo[1,5-a]pyrimidines from 4-hydroxy-6-methylpyran-2-one
    Elotmani, B
    El Hakmoui, A
    Essassi, EM
    Fifani, J
    Gueiffier, A
    COMPTES RENDUS DE L ACADEMIE DES SCIENCES SERIE II FASCICULE C-CHIMIE, 2001, 4 (04): : 285 - 288
  • [33] DERIVATED COMPOUNDS FROM 4-HETHEROALKANALS .1. SYNTHESIS, DERIVATIVES AND ACID-CATALYZED TRANSFORMATION OF 6-HYDROXY-4-OXA-HEXANAL
    UBEDA, AE
    MEZO, MAG
    ROSA, JC
    ANALES DE QUIMICA SERIE C-QUIMICA ORGANICA Y BIOQUIMICA, 1982, 78 (02): : 232 - 235
  • [34] NOVEL REACTION OF CARBON SUBOXIDE - SYNTHESIS OF 6-AMINO-4-HYDROXY-2(1H)-PYRIDONE DERIVATIVES
    BONSIGNORE, L
    COCCO, MT
    LOY, G
    ONNIS, V
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1992, 29 (01) : 237 - 239
  • [35] Solvent-free synthesis of 3-benzylpyrano [3,2-c] pyran/chromene-2,5-diones via tandem reaction of 4-hydroxy-6-methyl-pyran-2-one and 4-hydroxycoumarin with Baylis-Hillman adduct acetates
    Moghaddam, F. Matloubi
    Foroushani, B. Koushki
    Kalahroodi, E. Lotfi
    SCIENTIA IRANICA, 2014, 21 (03) : 735 - 741
  • [36] Design, synthesis and pharmacological evaluation of 6-hydroxy-4-methylquinolin-2(1H)-one derivatives as inotropic agents
    Sadeghian, Hamid
    Seyedi, Seyed Mohammad
    Saberi, Mohammad Reza
    Nick, Reza Shafiee
    Hosseini, Azar
    Bakavoli, Mehdi
    Mansouri, Seyed Mohammad Taghi
    Parsaee, Heydar
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2009, 24 (04) : 918 - 929
  • [37] A novel and efficient synthesis of 3,3′-benzylidenebis(4-hydroxy-6-methylpyridin-2(1H)-one) derivatives through a multi-component reaction catalyzed by L-proline
    Shi, Chun-Ling
    Shi, Da-Qing
    Kim, Sung Hong
    Huang, Zhi-Bin
    Ji, Min
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2008, 61 (07) : 547 - 551
  • [38] Benzylidene-bis-(4-Hydroxycoumarin) and Benzopyrano-Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformational and X-ray Crystal Structure Studies and In Vitro Antiviral Activity Evaluations
    Zavrsnik, Davorka
    Muratovic, Samija
    Makuc, Damjan
    Plavec, Janez
    Cetina, Mario
    Nagl, Ante
    De Clercq, Erik
    Balzarini, Jan
    Mintas, Mladen
    MOLECULES, 2011, 16 (07): : 6023 - 6040
  • [39] Efficient, Concise, and Chemoselective Synthesis of 1H-Benzo[f]indole-4,9-dione with 4-Hydroxycoumarin Substituent via a One-Pot Three-Component Reaction
    Alizadeh, Abdolali
    Hasanpour, Hamidreza
    Rezaiyehraad, Reza
    CHEMISTRYSELECT, 2023, 8 (48):
  • [40] One-step synthesis of dialkyl 2-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3,4-dicarboxylates by reaction of acetylenedicarboxylates with 'tosylmethyl isocyanide' (TsMIC) and triphenylphosphine
    Alizadeh, Abdolah
    Masrouri, Hassan
    Rostamnia, Sadegh
    Movahedi, Farnaz
    HELVETICA CHIMICA ACTA, 2006, 89 (05) : 923 - 926