Synthesis of Pyridines via Copper-catalyzed Reaction of Oxime Acetates with Benzyl Alcohols

doi:10.11944/j.issn.1000-0518.2016.11.160026

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (11): 1289-1294.DOI: 10.11944/j.issn.1000-0518.2016.11.160026

• Full Papers • Previous Articles Next Articles

Synthesis of Pyridines via Copper-catalyzed Reaction of Oxime Acetates with Benzyl Alcohols

SHI Yun(),REN Chaojie,ZHANG Ning

College of Chemistry and Chemical Engineering,Lanzhou University,Lanzhou 730000,China

Received:2016-01-15 Accepted:2016-05-11 Published:2016-11-01 Online:2016-11-01
Contact: SHI Yun
Supported by:
Supported by National Natural Science Foundation of China(No.21101663), Gansu Province Youth Science and Technology Fund Project(No.1107RJYA080)

Abstract

Abstract:

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.

Key words: oxime acetate, benzyl alcohol, copper-catalyzed, pyridine derivative, one-pot reaction

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.

References

[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]	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]	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]	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]	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]	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]	Kelly T R,Lebedev R L.Synthesis of Some Unsymmetrical Bridged Terpyridines[J]. J Org Chem,2002,67(7):2197-2205.
[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]	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]	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]	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]	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]	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.

Synthesis of Pyridines via Copper-catalyzed Reaction of Oxime Acetates with Benzyl Alcohols

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 11

Recommended Articles

Metrics

Comments

[1]	TIAN Shu-Yang, LYU Rong-Wen. Solvent-Free Oxidation of Benzyl Alcohol to Benzaldehyde Catalyzed by Magnesium Oxide Supported Bimetallic Gold-Palladium [J]. Chinese Journal of Applied Chemistry, 2021, 38(7): 789-799.
[2]	HUANG Jieying, LIU Jianjun, ZUO Shengli, HAN Wenjing, YU Yingchun. Preparation of Ag₃PO₄ Quantum Dots/g-C₃N₄ Nanosheet Composite Photocatalysts and Its Activity for Selective Oxidation of Benzyl Alcohol [J]. Chinese Journal of Applied Chemistry, 2020, 37(9): 1030-1037.
[3]	TANG Zilong, TAN Jingzhao, CAI Lanqiong, LI Xinxing, LIU Wanqiang. Synthesis and Fungicidal Activity of Novel 2-(Arylaminoethylamino)benzyl Alcohols [J]. Chinese Journal of Applied Chemistry, 2017, 34(3): 345-353.
[4]	CHANG Yu, XIE Wenbing, ZHOU Shihong, LI Junling, LIU Baofeng, PAN Lihua. Synthesis and Spectroscopic Properties of a Cryptate Rare Earth Fluorescence Complex [J]. Chinese Journal of Applied Chemistry, 2017, 34(3): 361-366.
[5]	LIU Jie,ZHOU Weiyou,WU Zhong,SUN Fu'an,HE Mingyang,CHEN Qun. Selective Oxidation of Benzyl Alcohol to Benzaldehyde Catalyzed by Co₂/Al/Mg_x Hydrotalcite-like Materials in Liquid Phase [J]. Chinese Journal of Applied Chemistry, 2015, 32(9): 1033-1039.
[6]	SU Hao, YANG Chun*. Selective Oxidation of Benzyl Alcohol Catalyzed by Polyoxometalates:A Green Recyclable Catalytic System with High Performance [J]. Chinese Journal of Applied Chemistry, 2014, 31(08): 958-964.
[7]	MA Congming1, LIU Zuliang1, YAO Qizheng1,2*. Synthesis and Characterization of 5-Substituted Furoxano[3,4-b]pyridine Derivatives [J]. Chinese Journal of Applied Chemistry, 2014, 31(08): 911-915.
[8]	SUN Xiaoyun1,2,3, LI Jing3, YUE Shuang3, DU Yanfang3, ZANG Shuliang3*. Methyltri-n-octylammonium Peroxotungstate Ionic Liquid Catalized Hydrogen Peroxide Oxidation of Benzyl Alcohol to Benzoic Acid [J]. Chinese Journal of Applied Chemistry, 2013, 30(04): 394-397.
[9]	ZHAO Zhouxing. Three-Component One-Pot Synthesis of (E)-β-(Alkoxy)arylethylenes [J]. Chinese Journal of Applied Chemistry, 2013, 30(02): 148-152.
[10]	RONG Li-Xia1, HE Kai2, FANG Yan-Xiong1*, JI Hong-Bing3, ZHANG Kun1. Oxydation of Benzyl Alcohol Catalyzed by Chloridizing Metallic Porphyrin Immobilized in Ionic Liquid [J]. Chinese Journal of Applied Chemistry, 2010, 27(10): 1124-1128.
[11]	HAO Fu-Ying, YIN Jian-Hui, GAN Xiao-Ping, GENG Wen-Qian, XU Guo-Yi, TUN Jie-Ying, TIAN Yu-Peng, ZHOU Hong-Bing. Synthesis of Carbazole derivatives with Two-photon absorption via Solid-state method and Optical storage application [J]. Chinese Journal of Applied Chemistry, 2009, 26(11): 1277-1281.