Cerium(IV) ammonium nitrate-catalyzed synthesis of β-keto enol ethers from cyclic β-diketones and their deprotection

被引:32
|
作者
Banerjee, B [1 ]
Mandal, SK [1 ]
Roy, SC [1 ]
机构
[1] Indian Assoc Cultivat Sci, Dept Organ Chem, Kolkata 700032, W Bengal, India
关键词
D O I
10.1246/cl.2006.16
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A mild and efficient method for etherification of cyclic beta-diketones with alcohols has been developed Using a catalytic amount of cerium(IV) ammonium nitrate at room temperature to afford the corresponding beta-keto enol ethers in good to excellent yields. The deprotections of enol ethers in water-acetonitrile (1:1) using a catalytic amount (10 mol %) of cerium(IV) ammonium nitrate have also been achieved.
引用
收藏
页码:16 / 17
页数:2
相关论文
共 50 条
  • [31] Synthesis of fused acetals by ceric ammonium nitrate mediated cycloaddition of 1,3-dicarbonyl compounds to cyclic enol ethers
    Roy, SC
    Mandal, PK
    TETRAHEDRON, 1996, 52 (38) : 12495 - 12498
  • [32] Ceric ammonium nitrate-catalyzed tetrahydropyranylation of alcohols and synthesis of 2-deoxy-O-glycosides
    Pachamuthu, K
    Vankar, YD
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (22): : 7511 - 7513
  • [33] FACILE PALLADIUM-CATALYZED CARBONYLATION OF TRIARYLSTIBINES IN THE PRESENCE OF AMMONIUM CERIUM(IV) NITRATE
    CHO, CS
    TANABE, K
    ITOH, O
    UEMURA, S
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (01): : 274 - 275
  • [34] Regeneration of carbonyl compounds from azines with cerium(IV) ammonium nitrate
    Giurg, M
    Mlochowski, J
    SYNTHETIC COMMUNICATIONS, 1999, 29 (24) : 4307 - 4313
  • [35] Regeneration of carbonyl compounds from azines with cerium(IV) ammonium nitrate
    Inst. Organ. Chem. Biochem. Biotech., Wroclaw University of Technology, Wyb. Wyspianskiego 27, 50-370 Wroclaw, Poland
    Synth. Commun., 24 (4307-4313):
  • [36] Convenient synthesis of substituted pyrroles via a cerium (IV) ammonium nitrate (CAN)-catalyzed Paal-Knorr reaction
    Kamal, Ahmed
    Faazil, Shaikh
    Malik, M. Shaheer
    Balakrishna, Moku
    Bajee, Shaik
    Siddiqui, M. Rafique H.
    Alarifi, Abdullah
    ARABIAN JOURNAL OF CHEMISTRY, 2016, 9 (04) : 542 - 549
  • [37] Fully Diastereoselective Synthesis of Polysubstituted, Functionalized Piperidines and Decahydroquinolines Based on Multicomponent Reactions Catalyzed by Cerium(IV) Ammonium Nitrate
    Suryavanshi, Padmakar A.
    Sridharan, Vellaisamy
    Maiti, Swarupananda
    Carlos Menendez, J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (28) : 8791 - 8799
  • [38] REGIOSELECTIVE OXIDATION OF POLYALKOXY NAPHTHALENES - FORMATION OF NAPHTHOQUINONES BY AMMONIUM CERIUM(IV) NITRATE OXIDATION OF METHOXYMETHYL ETHERS
    CLIVE, DLJ
    MIDDLETON, DS
    ISRAEL JOURNAL OF CHEMISTRY, 1991, 31 (03) : 211 - 213
  • [39] Synthesis of 1,4-Diketones from -Oxo Esters and Enol Acetates by Cerium-Catalyzed Oxidative Umpolung Reaction
    Geibel, Irina
    Christoffers, Jens
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (05) : 918 - 920
  • [40] Microwave thermolysis IV: Selective deprotection of MPM ethers using clay supported ammonium nitrate "clayan" in dry media
    Yadav, JS
    Meshram, HM
    Reddy, GS
    Sumithra, G
    TETRAHEDRON LETTERS, 1998, 39 (19) : 3043 - 3046