A Mild Protocol foor the Efficient Synthesis of 5,6-Unsubstituted 1,4-Dihydropyridines

被引:19
|
作者
Maiti, Swarupanada [1 ]
Menendez, J. Carlos [1 ]
机构
[1] Univ Complutense Madrid, Fac Farm, Dept Quim Organ & Farmaceut, Madrid 28040, Spain
关键词
eliminations; heterocycles; dihydropryidines; cerium(IV); Lewis acids; 3-COMPONENT DOMINO SYNTHESIS; CHEMICAL DELIVERY-SYSTEMS; MULTIDRUG-RESISTANCE; SUBSTITUTED 1,4-DIHYDROPYRIDINES; PRIVILEGED STRUCTURES; MEDICINAL CHEMISTRY; TETRAHYDROQUINOLINE SYSTEMS; MULTICOMPONENT REACTIONS; 4+2 CYCLOADDITIONS; HANTZSCH REACTION;
D O I
10.1055/s-0029-1217719
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of 6-alkoxy-1,4,5,6-tetrahydropyridines with neutral alumina (activity grade I) suspended in refluxing aceto-nitrile, afforded 1,4-dihydropyridines in excellent yields. This method allowed the efficient synthesis of 5,6-unsubstituted dihydropyridines, which are difficult to prepare by traditional methods, from acyclic and readily available precursors.
引用
收藏
页码:2249 / 2252
页数:4
相关论文
共 50 条
  • [41] New Efficient Protocol for the Production of Hantzsch 1,4-Dihydropyridines Using RuCl3
    Suresh
    Kumar, Dhruva
    Sandhu, Jagir S.
    SYNTHETIC COMMUNICATIONS, 2009, 39 (11) : 1957 - 1965
  • [42] Efficient oxidation of Hantzsch 1,4-dihydropyridines with nicotinium dichromate
    Sadeghi, MM
    Mohammadpoor-Baltork, I
    Memarian, HR
    Sobhani, S
    SYNTHETIC COMMUNICATIONS, 2000, 30 (09) : 1661 - 1665
  • [43] Comparative Study of Various Green Chemistry Approaches for the Efficient Synthesis of 1,4-Dihydropyridines
    Kaur, Prabhjot
    Sharma, Heena
    Rana, Rekha
    Prasad, D. N.
    Singh, Rajesh K.
    ASIAN JOURNAL OF CHEMISTRY, 2012, 24 (12) : 5649 - 5651
  • [44] Rapid and cleaner synthesis of 1,4-dihydropyridines in aqueous medium
    Sivamurugan, V.
    Vinu, A.
    Palanichamy, M.
    Murugesan, V.
    HETEROATOM CHEMISTRY, 2006, 17 (04) : 267 - 271
  • [45] Synthesis of the C-2 functionalized 1,4-dihydropyridines
    Zenouz, AM
    Allahverdi, S
    Raissossadat, M
    Sadeghi, Q
    ASIAN JOURNAL OF CHEMISTRY, 2005, 17 (04) : 2639 - 2643
  • [46] UNEQUIVOCAL SYNTHESIS OF N-SUBSTITUTED 1,4-DIHYDROPYRIDINES
    STOUT, DM
    TAKAYA, T
    MEYERS, AI
    JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (05): : 563 - 569
  • [47] Synthesis of Hantzsch 1,4-dihydropyridines under microwave irradiation
    Anniyappan, M
    Muralidharan, D
    Perumal, PT
    SYNTHETIC COMMUNICATIONS, 2002, 32 (04) : 659 - 663
  • [48] SYNTHESIS OF HANTZSCH 1,4-DIHYDROPYRIDINES IN A CONTINUOUS FLOW MICROREACTOR
    Gao, Peiyuan
    Sun, Xuan
    Lei, Ming
    Zhang, Hong
    HETEROCYCLES, 2016, 93 (02) : 755 - 761
  • [49] Design and synthesis of ferrocenyl 1,4-dihydropyridines and their evaluation as kinesin-5 inhibitors
    Kowalczyk, Karolina
    Blauz, Andrzej
    Krawczyk, Krzysztof
    Rychlik, Blazej
    Plazuk, Damian
    DALTON TRANSACTIONS, 2024, 53 (38) : 16038 - 16053
  • [50] Hydrated ferric sulfate catalyzed synthesis of 5,6-unsubstittitted 1,4-dihydropyridines using three-component reaction
    Islam, Kobirul
    Das, Deb K.
    Khan, Abu T.
    TETRAHEDRON LETTERS, 2014, 55 (41) : 5613 - 5617