Citation:
SHI Yun, REN Chaojie, ZHANG Ning. Synthesis of Pyridines via Copper-catalyzed Reaction of Oxime Acetates with Benzyl Alcohols[J]. Chinese Journal of Applied Chemistry,
;2016, 33(11): 1289-1294.
doi:
10.11944/j.issn.1000-0518.2016.11.160026
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Pyridine derivatives were synthesized in a one-pot reaction from oxime acetates and benzyl alcohols in the presence of copper(Ⅱ) trifluoromethanesulfonate[Cu(OTf)2] catalyst. The effect of catalysts and their dosage, raw material ratios, solvents, and temperatures on the yield were investigated. The target compound 2,4,6-trisubstituted pyridine was obtained in 88% yield under the optimum condition. The molecular structures of products were analyzed by mass spectrometry and nuclear magnetic resonance spectroscopy(1H NMR and 13C NMR). The method has several advantages:commerically available materials, easy operation, mild reaction conditions, good yields and a wide range of functional group tolerance.
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[1]
[1] Bagleym C,Bashford K E,Hesketh C L,et al. Total Synthesis of the Thiopeptidepromothiocin A[J]. J Am Chem Soc,2000,122(14):3301-3313.
-
[2]
[2] Roughley S D,Jordan A M. The Medicinal Chemist's Toolbox:An Analysis of Reactions Used in the Pursuit of Drug Candidates[J]. J Med Chem,2011,54(10):3451-3479.
-
[3]
[3] Gibson V C,Redshaw C,SolanG A. Bis(imino)pyridines:Surprisingly Reactive Ligands and a Gateway to New Families of Catalysts[J]. Chem Rev,2007,107(5):1745-1776.
-
[4]
[4] Girgis A S,Hosni H M,Barsoum F F. Novel Synthesis of Nicotinamide Derivatives of Cytotoxic Properties[J]. Bioorg Med Chem,2006,14(13):4466-4476.
-
[5]
[5] Bull J A,Mousseau J J,Pelletier G,et al. Synthesis of Pyridine and Dihydropyridine Derivatives by Regio- and Stereoselectiveaddition to N-Activated Pyridines[J]. Chem Rev,2012,112(5):2642-2713.
-
[6]
[6] Too P C,Wang Y F,Chiba S. Rhodium(Ⅲ)-Catalyzed Synthesis of Isoquinolines from Aryl Ketone O-Acyloxime Derivatives and Internal Alkynes[J]. Org Lett,2010,12(24):5688-5691.
-
[7]
[7] Kelly T R,Lebedev R L. Synthesis of Some Unsymmetrical Bridged Terpyridines[J]. J Org Chem,2002,67(7):2197-2205.
-
[8]
[8] Li Z Y,Huang X Q,Chen F,et al. Cu-Catalyzed Concise Synthesis of Pyridines and 2-(1H)-Pyridones from Acetaldehydes and Simple Nitrogen Donors[J]. Org Lett,2015,17(3):584-587.
-
[9]
[9] Colby D A,Bergman R G,Ellman J A. Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C-H Activation[J]. J Am Chem Soc,2008,130(11):3645-3651.
-
[10]
[10] Ren Z H,Zhang Z Y,Yang B Q,et al. Copper-Catalyzed Coupling of Oxime Acetates with Adehydes:A New Strategyfor Synthesis of Pyridines[J]. Org Lett,2011,13(19):5394-5397.
-
[11]
[11] Wang Y,Chen C,Peng J,et al. Copper(Ⅱ)-Catalyzed Three-Component Cascade Annulation of Diaryliodoniums, Nitriles, and Alkynes:A Regioselective Synthesis of Multiply Substituted Quinolines[J]. Angew Chem Int Ed,2013,52(20):5323-5327.
-
[12]
[12] Trost B M,Rhee Y H. A Ru Catalyzed Divergence:Oxidative Cyclization vs Cycloisomerization of Bis-homopropargylic Alcohols[J]. J Am Chem Soc,2002,124(11):2528-2533.
-
[13]
[13] Takai K,Katsura N,Kunisada Y. Generation of Chromioenamines by Reduction of O-Acetyloximes with Chromium(Ⅱ) and Their Application[J]. Chem Commun,2001,(18):1724-1725.
-
[1]
-
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