Ionic liquid i.e. 1-Pentyl-3-methylimidazolium Bromide Mediated Synthesis of 2-phenylbenzoxazole
Keywords:
Ionic liquid, Microwave, [pmIm]Br, Imidazolium, Catalyst-free, Green chemistryAbstract
An efficient and green synthesis of 2-phenylbenzoxazole have been carried out by a simple condensation of 2-aminophenol and aromatic aldehyde in an inexpensive ionic liquid i.e. 1-pentyl-3-methylimidazolium bromide ([pmIm]Br) by microwave irradiation under solvent free condition. Initially, imidazolium based ionic liquid i.e. 1-Pentyl-3-methylimidazolium bromide [pmIm]Br have been synthesized by microwave irradiation from 1-methylimidazole and n-pentyl bromide. The structure of newly synthesized ionic liquid and 2-phenylbenzoxazole have been confirmed by spectral studies such as UV-Vis, FT-IR and 1H-NMR spectroscopy techniques. Ionic liquid i. e. [pmIm]Br as a reaction media offers several advantages including non-toxic, non-corrosive, shorter reaction time, high yield of the products, mild reaction conditions as well as simple experimental and isolation procedures.
References
A. Rajendran, A. Selvam, C. Karthikeyan, S. Ramu, “An ionic liquid catalysed facile green synthesis of phenyl polyhydro-1, 8-acridine diones”. Int J Cur Tr Res. Vol. 1, issue 1, pp. 24-30, 2012
J. Huddlesto, A. Viser, W. Reichert, H. Willauer, G. Broker and R. Rogers, “Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation” . Green Chem., Vol. 3, pp. 156, 2001
Li Ruxiong, Green Solvents: Synthesis and Application of Ionic Liquids, Beijing: Chemical Industry Press, Vol. 6, 2004.
K. Mikami, Green Reaction Media in Organic Synthesis, Blackwell Publishing, Oxford, 2005.
A. Zare, A. Parhami, A. R. Moosavi-Zare, A. Hasaninejad, A. Khalafi-Nezhad, M. H. Beyzavi, “A catalyst-free protocol for the green and efficient condensation of indoles with aldehydes in ionic liquids”. Can. J. Chem. Vol. 87, Issue 2, pp. 416-421, 2009.
A. Zare, A. Hasaninejad, M. H. Beyzavi, A. R. Moosavi Zare, A. Khalafi-Nezhad, F. Asadi, L. Baramaki, S. Jomhori-Angali, R. Ghaleh-Golabi, “KF/Al2O3 as a highly efficient, green, heterogeneous, and reusable catalytic system for the solvent-free synthesis of carboacyclic nucleosides via Michael addition reaction.” Synth. Commun. , Vol. 39, pp. 139 – 157, 2009.
P. Wasserscheid, T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2003.
X. Li, W. Eli, G. Li, “Solvent-free synthesis of benzoic esters and benzyl esters in novel Brønsted acidic ionic liquids under microwave irradiation”. Catal. Commun. Vol. 9, pp. 2264-2268, 2008.
Y. Peng, G. Song, “Microwave-assisted clean synthesis of 6-aryl-2,4-diamino-1,3,5-triazines in [Bmim][PF6]”. Tetrahedron Lett., Vol. 45, pp. 5313-5316, 2004.
A. Romero, A. Santos, J. Tojo, A. Rodriguez, “Toxicity and biodegradability of imidazolium ionic liquids”. J Hazard Mater. Vol. 151, pp. 268–273, 2008.
C. Benedi, F. Bravo, P. Uriz, E. Fernandez, C. Claver, and S. Castillon, “Synthesis of 2-substituted-benzothiazoles by palladium-catalyzed intramolecular cyclization of o-bromophenylthioureas and o-bromophenylthioamides”, Tetrahedron Lett., Vol. 44, pp. 6073, 2003.
K.S.A. Vallin, P. Emilsson, M. Larhed, A. Hallberg, “High-speed Heck reactions in ionic liquid with controlled microwave heating”. J. Org. Chem., Vol. 67, pp. 6243-6246, 2002.
J.S. Yadav, B.V.S. Reddy, L. Chetia, G. Srinivasulu, A.C. Kunwar, “Ionic liquid accelerated intramolecular hetero-Diels–Alder reactions: a protocol for the synthesis of octahydroacridines.” Tetrahedron Lett., Vol. 46, pp. 1039-1044, 2005.
V. Namboordiri and R. S. Varma, “Solvent-Free Sonochemical Preparation of Ionic Liquids”. Org. Lett., vol. 4, issue 18, pp. 3161-3163, 2002.
V. I. Parvulescu, C. Hardacre, “Catalysis in ionic liquids”. Chem. Rev. vol. 107, issue 6, pp. 2615–2665, 2007
P. L. Anto, C. Y. Panicker, H. T. Varghese, D. Philip, O. Temiz-Arpaci, B. Tekiner-Gulbas, I. Yildiz, “Vibrational spectroscopic studies and ab initio calculations of 5-methyl-2-(p-fluorophenyl)benzoxazole”. Spectrochim. Acta Part A, vol. 67, pp. 744-749, 2007
R. M. Silverstein, F. X. Webster, Spectrometric Identification of Organic Compounds, sixth ed., John Wiley, Asia, 2003.
R. Saxena, L. D. Kaudpal, G. N. Mathur, “Synthesis and characterization of poly(benzobisthiazole)s derived from halogenated phthalic acid and isophthalic acid”. J. Polym. Sci. Part A: Polym. Chem. vol. 40, pp. 3959-3966, 2002.
K. Nakamoto, Infrared and Raman Spectrum of Inorganic and coordination Compounds,5th ed., John Wiley and Sons, Inc., New York, 1997.
S. Kantevari, S.V.N. Vuppalapati, L. Nagarapu, “Montmorillonite K10 catalyzed efficient synthesis of amidoalkyl naphthols under solvent free conditions”. Catal. Commun., Vol. 8, pp. 1857-1862, 2007.
N. B. Colthup, L. H. Daly, S. E. Wiberly, Introduction to Infrared and Raman Spectroscopy, 3rd ed., Academic Press, Boston, 1990.
J. Coates, R. A. Meyers (Ed.), Encyclopedia of Analytical Chemistry; Interpretation of Infrared Spectra, A Practical Approach, John Wiley and Sons Ltd., Chichester, 2000.
J.S. Yadav, B.V.S. Reddy, L. Chetia, G. Srinivasulu, A.C. Kunwar, “Ionic liquid accelerated intramolecular hetero-Diels–Alder reactions: a protocol for the synthesis of octahydroacridines”. Tetrahedron Lett., Vol. 46 pp. 1039-1044, 2005.
B.C. Ranu, S.S. Dey, A. Hajra, “Catalysis by an ionic liquid: efficient conjugate addition of thiols to electron deficient alkenes catalyzed by molten tetrabutylammonium bromide under solvent-free conditions”. Tetrahedron, Vol. 59, issue 14, 2417-2421, 2003.
B. C. Ranu, A. Hajra, and S. S. Dey, “A practical and green approach towards synthesis of dihydropyrimidinones without any solvent or catalyst”. Org. Process Res. Dev., vol. 6, pp. 817, 2002.
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