Microwave-Assisted Synthesis of Benzoxazoles in Glycerol

doi:10.11944/j.issn.1000-0518.2017.03.160243

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (3): 324-329.DOI: 10.11944/j.issn.1000-0518.2017.03.160243

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Microwave-Assisted Synthesis of Benzoxazoles in Glycerol

LEI Jiao^a,LUO Li^a,FU Weiwei^a,ZHOU Wenjun^a^b^*()

^aCollege of Chemistry and Chemical Engineering
^bKey Laboratory of Fruit Waste Treatment and Resource Recycling of the Sichuan Provincial College,Neijiang,Sichuan 641112,China

Received:2016-06-13 Accepted:2016-08-15 Published:2017-02-27 Online:2017-02-27
Contact: ZHOU Wenjun
Supported by:
Supported by the Sichuan Province Education Office Fostering Projects(No.15Z0026), the Startup Foundation of Ph. D. Scientific Research of Neijiang Normal University(No.2012B05)

Abstract

Abstract:

Benzoxazole derivatives are well known for their applications in medicinal, industrial and synthetic organic chemistry. Numerous effects has been focused on developing efficient methods for the synthesis of it. The benzoxazole derivatives was synthesised by condensation of 2-aminophenol and benzaldehyde in presence of glycerol under focused microwave-irradiation conditions. Reaction conditions:2-aminothiophenol(1.0 mmol), benzaldehyde(1.0 mmol), glycerol(2 mL), irradiating under focused microwave for several minutes at 20 W and 110 ℃. The corresponding products was obtained in 80% to 91% yield. The present method has the advantages of mild conditions, green solvent, simple operation, easily available reaction substrates, and excellent product yields, which make it a useful and important supplement to the existing methods.

Key words: benzoxazole, glycerol, aminophenol, aromatic aldehydes

LEI Jiao, LUO Li, FU Weiwei, ZHOU Wenjun. Microwave-Assisted Synthesis of Benzoxazoles in Glycerol[J]. Chinese Journal of Applied Chemistry, 2017, 34(3): 324-329.

References

[1]	Seenaiah D,Reddy P R,Reddy G M,et al.Synthesis, Antimicrobial and Cytotoxic Activities of Pyrimidinyl Benzoxazole, Benzothiazole and Benzimidazole[J]. Eur J Med Chem,2014,77(22):1-7.
[2]	Wee D,Yoo S,Kang Y H,et al.Poly(imide-benzoxazole) Gate Insulators with High Thermal Resistance for Solution-processed Flexible Indium-zinc Oxide Thin-film Transistors[J]. J Mater Chem:C,2014,2(31):6395-6401.
[3]	Dick P F,Coelho F L,Rodembusch F S,et al.Amphiphilic ESIPT Benzoxazole Derivatives as Prospective Fluorescent MembraneProbes[J]. Tetrahedron Lett,2014,55(19):3024-3029.
[4]	XIAO Liwei,GAO Hongjie,KONG Jie,et al.Progress in the Synthesis of 2-Substituted Benzoxazoles Derivatives[J]. Chinese J Org Chem,2014,34(10):1048-1060(in Chinese). 肖立伟,高红杰,孔洁,等. 2-取代苯并噁唑类化合物合成研究进展[J]. 有机化学,2014,34(10):1048-1060.
[5]	Kawashita Y,Nakamichi N,Kawabata H,et al.Direct and Practical Synthesis of 2-Arylbenzoxazoles Promoted by Activated Carbon[J]. Org Lett,2003,5(21):3713-3715.
[6]	Gu L J,Jin C,Guo J M,et al.A Novel Strategy for the Construction of Substituted Benzoxazoles via a Tandem Oxidative Process[J]. Chem Commun,2013,49(93):10968-10970.
[7]	Wu M,Hu X,Liu J,et al.Iron-Catalyzed 2-Arylbenzoxazole Formation from o-Nitrophenols and Benzylic Alcohols[J]. Org Lett,2012,14(11):2722-2725.
[8]	Jin X,Liu Y,Lu Q,et al.Formation of C=N Double BondS by the Release of H2:A New Strategy for Synthesis of Imines and Benzazoles[J]. Org Biomol Chem,2013,11(23):3776-3780.
[9]	Wu X F,Neumann H,Neumann S,et al.Sequential One-pot Synthesis of Benzoxazoles from Aryl Bromides:Successive Palladium- and Copper-catalyzed Reactions[J]. Tetrahedron Lett,2013,54(24):3040-3042.
[10]	Ranjit S,Liu X G. Direct Arylation of Benzothiazoles and Benzoxazoles with Aryl Boronic Acids[J]. Chem Eur J,2011,17(4):1105-1108.
[11]	Guru M M,Ali M A,Punniyamurthy T. Copper(II)-Catalyzed Conversion of Bisaryloxime Ethers to 2-Arylbenzoxazoles via C—H Functionalization/C—N/C—O Bonds Formation[J]. Org Lett,2011,13(5):1194-1197.
[12]	Hoogendoorn A,van Kasteren H. Transportation Biofuels Novel Pathways for the Production of Ethanol, Biogas and Bio-diesel[M]. RSC Publishing,Cambridge,2010.
[13]	Pagliaro M,Rossi M. The Future of Glycerol:New Usages for a Versatile Raw Material[M]. RSC Publishing,Cambridge,2008.
[14]	ZHANG Xiazhong,ZOU Runying,DENG Jiaying,et al.Recent Progress of Glycerol as Green Solvents in Organic Synthesis[J]. Chinese J Org Chem,2015,35(6):1238-1249(in Chinese). 张霞忠,邹润英,邓家英,等. 甘油作绿色溶剂在有机合成中的应用研究进展[J]. 有机化学,2015,35(6):1238-1249.
[15]	Díaz-Álvarez A E,Francos J,Lastra-Barreira B,et al. Glycerol and Derived Solvents:New Sustainable Reaction Media for Organic Synthesis[J]. Chem Commun,2011,47(21):6208-6227.
[16]	Gu Y,Jérôme F. Glycerol as A Sustainable Solvent for Green Chemistry[J]. Green Chem,2010,12(7):1127-1138.
[17]	ZHOU Yu,HE Yuan,ZHOU Wenjun. Adsorption of Palladium by Pectin and Its Application in Organic Synthesis[J]. Chinese J Appl Chem,2015,32(12):1402-1409(in Chinese). 周宇,何媛,周文俊. 果胶对钯的吸附及其在有机合成中的应用[J]. 应用化学,2015,32(12):1402-1409.
[18]	ZHOU Wenjun,ZHOU Dan,ZHANG Xiazhong,et al.Synthesis of Quinoxaline Derivatives Using Glycerol as Phase Transfer Catalyst[J]. Chem Res Appl,2015,27(6):919-922(in Chinese). 周文俊,周丹,张霞忠,等. 甘油作为相转移催化剂催化合成喹噁啉类化合物[J]. 化学研究与应用,2015,27(6):919-922.
[19]	Zhang X H,Zhou W J,Yang M,et al.Microwave-assisted Synthesis of Benzothiazole Derivatives Using Glycerol as Green Solvent[J]. J Chem Res,2012,36(8):489-491.
[20]	Blacker A J,Farah M M,Marsden S P,et al.Oxidative Conversion of Amines into Benzoxazoles Using Hydrogen Transfer Catalysis[J]. Tetrahedron Lett,2009,50(45):6106-6109.
[21]	Wang L,Ma Z G,Wei X J,et al.Synthesis of 2-Substituted Pyrimidines and Benzoxazoles via a Visible-light-driven Organocatalytic Aerobic Oxidation:Enhancement of the Reaction Rate and Selectivity by a Base[J]. Green Chem,2014,16(8):3752-3757.

Microwave-Assisted Synthesis of Benzoxazoles in Glycerol

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