A Simple and Convenient Method for the Synthesis of Pyrano[3,2-c] chromenes via Sequential Three Component Reaction

被引:5
|
作者
Alizadeh, Abdolali [1 ]
Moafi, Leila [1 ]
机构
[1] Tarbiat Modares Univ, Dept Chem, POB 14115-175, Tehran, Iran
关键词
Pyrano[3,2-c]chromenes; activated alkynes; multicomponent reaction; 4-hydroxycoumarin; anti microbial; anti coagulant; MULTICOMPONENT REACTION; EFFICIENT SYNTHESIS; DERIVATIVES;
D O I
10.2174/1570178614666170710100020
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Background: Pyrano[3,2-c]chromenes are important frameworks of various natural products and have attracted much attention due to their biological activities. These properties include spasmolytic, anti microbial, anti coagulant, anti tumor and central nervous system activities. Methods: we described a convenient method for the preparation of functionalized pyrano[3,2-c] chromenes from the reaction of malononitrile, activated alkynes and 4-hydroxycoumarin in the presence of Et3N in EtOH at reflux condition. Result: Five pyrano[3,2-c]chromene derivatives were synthesized in high yield and their structures were completely characterized by spectroscopic techniques and elemental analysis. These products have potential applications in medicinal chemistry and in organic synthesis. Conclusion: A practical procedure one pot, three component reaction of readily available starting materials to give pyrano[3,2-c]chromene compounds has been developed. This method has some advantages like mild reaction condition, experimental simplicity, easy purification of products and does not require any metal-catalyst.
引用
收藏
页码:45 / 48
页数:4
相关论文
共 50 条
  • [31] 2H-Pyrano[3,2-c]quinolin-2-ones: their convenient synthesis and selected reactions
    Matúš Čakurda
    Pavol Koiš
    Gabriela Addová
    Margita Lácová
    Andrej Boháč
    Chemical Papers, 2018, 72 : 683 - 690
  • [32] A convenient synthesis of furo[3,2-c]coumarins by a tandem alkylation/intramolecular aldolisation reaction
    Risitano, F
    Grassi, G
    Foti, F
    Bilardo, C
    TETRAHEDRON LETTERS, 2001, 42 (20) : 3503 - 3505
  • [33] A mild and efficient method for the synthesis of a new class of furo[3,2-c]chromenes in aqueous media
    Khalilzadeh, Mohammad A.
    Hossaini, Zinatossadat
    Charati, Faramarz Rostami
    Hallajian, Sara
    Rajabi, Mehdi
    MOLECULAR DIVERSITY, 2011, 15 (02) : 445 - 450
  • [34] A mild and efficient method for the synthesis of a new class of furo[3,2-c]chromenes in aqueous media
    Mohammad A. Khalilzadeh
    Zinatossadat Hossaini
    Faramarz Rostami Charati
    Sara Hallajian
    Mehdi Rajabi
    Molecular Diversity, 2011, 15 : 445 - 450
  • [35] Efficient synthesis of new tricyclic pyrano[3,2-c]pyridine derivatives
    Mamedov, Ibrahim G.
    Khrustalev, Victor N.
    Dorovatovskii, Pavel V.
    Naghiev, Farid N.
    Maharramov, Abel M.
    MENDELEEV COMMUNICATIONS, 2019, 29 (02) : 232 - 233
  • [36] A synthesis of a new pyrano[3,2-c] quinolinedione derivative assisted by microwaves
    Bratulescu, George
    LETTERS IN ORGANIC CHEMISTRY, 2008, 5 (02) : 133 - 136
  • [37] Preparation and characterization of MNPs-PhSO3H as a heterogeneous catalyst for the synthesis of benzo[b]pyran and pyrano[3,2-c]chromenes
    Faroughi Niya, Homayoun
    Hazeri, Nourallah
    Rezaie Kahkhaie, Mahboobeh
    Maghsoodlou, Malek Taher
    RESEARCH ON CHEMICAL INTERMEDIATES, 2020, 46 (03) : 1685 - 1704
  • [38] Preparation and characterization of MNPs–PhSO3H as a heterogeneous catalyst for the synthesis of benzo[b]pyran and pyrano[3,2-c]chromenes
    Homayoun Faroughi Niya
    Nourallah Hazeri
    Mahboobeh Rezaie Kahkhaie
    Malek Taher Maghsoodlou
    Research on Chemical Intermediates, 2020, 46 : 1685 - 1704
  • [39] Green Synthesis of Pyrano[3,2-c]pyridine Derivatives in Ionic Liquids
    Zhang, Meimei
    Zhou, Yujing
    Li, Yuling
    Liu, Yun
    Wang, Xiangshan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2013, 33 (08) : 1728 - 1733
  • [40] A green and efficient one-pot three-component synthesis of dihydropyrano[3,2-c]chromenes using NaCl in hydroalcoholic media
    Sajadikhah, Seyed Sajad
    Maghsoodlou, Malek Taher
    Hazeri, Nourallah
    Norouzi, Mahmoud
    Moein, Maryam
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (11) : 8665 - 8672