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Current Organocatalysis


ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

Research Article

Ultrasonically Assisted Efficient and Green Protocol for the Synthesis of 4H-isoxazol-5-ones using Itaconic Acid as a Homogeneous and Reusable Organocatalyst

Author(s): Sandeep B. Kasar and Shankar R. Thopate*

Volume 6 , Issue 3 , 2019

Page: [231 - 237] Pages: 7

DOI: 10.2174/2213337206666190411115402


Background: Multicomponent reactions involve the simultaneous reaction of three or more components which deliver the product that incorporates the elements of all starting materials. A combination of multicomponent reaction and green solvents like water and the use of nonconventional energy sources like microwave or ultrasonication are important features of ideal green synthesis. Therefore, the design of a new multicomponent reaction and improvement of an already known multicomponent reaction with a green procedure has attracted the attention of the scientific community. Isoxazole derivatives are well known for their biological activities such as antifungal, analgesic, antitumor, antioxidant, antimicrobial, COX-2 inhibitory, anti-inflammatory, antiviral, and antimycobacterial.

Objective: To develop a green methodology for the synthesis of 4H-isoxazol-5-ones derivatives.

Result: Itaconic acid was used as a green catalyst for the synthesis of 4H-isoxazol-5-ones derivatives under conventional as well as ultrasound irradiation technique. Ultrasound irradiation condition requires less time for the completion of the reaction and also the yields were better.

Methods: We have reported Itaconic acid as a green homogenous organocatalyst under ultrasound irradiation for the synthesis of 4H-isoxazol-5-ones derivatives.

Conclusion: In conclusion, we have developed a green methodology for the synthesis of 4Hisoxazol- 5-ones derivatives. Itaconic acid is used as an organocatalyst which is biodegradable and nonhazardous. Water is used as a green solvent. Ultrasonication is used as a non-conventional green energy source. Ambient reaction conditions are used to carry out transformation for multicomponent reaction. Metal-free, mineral acid-free synthesis are key features of the present protocol.

Keywords: 4H-isoxazol-5-ones, homogenous, Itaconic acid, multicomponent reaction, organocatalyst, reusable, ultrasonication.

Graphical Abstract
Yanlong, G.U. Multicomponent reactions in unconventional solvents: state of the art. Green Chem., 2012, 14, 2091.
Wu, T.Y.; Guo, N.; Teh, C.Y.; Hay, J.X.W. Advances in Ultrasound Technology for Environmental Remediation; Springer Briefs in Green Chemistry for Sustainability, 2013.
Srivastava, R.M.; Filho, R.A.W.N.; Silva, C.A.; Bortoluzzi, A. First ultrasound-One-pot synthesis of N-substituted amides. Ultrason. Sonochem., 2009, 16, 737-742.
Santos, M.M.M.; Faria, N.; Iley, J.; Coles, S.J.; Hursthouse, M.B.; Martins, M.; Moreira, R. Reaction of naphthoquinones with substituted nitromethanes Facile synthesis and antifungal activity of naphtho[2,3-d]isoxazole-4,9-diones. Bioorg. Med. Chem. Lett., 2010, 20, 193-195.
Kano, H.; Adachi, I.; Ryonosuke, K.; Hirose, K. Isoxazoles. XVIII. Synthesis and Pharmacological Properties of 5-Aminoalkyl-and Aminoalkylisoxazoles and Related Derivatives. J. Med. Chem., 1967, 10, 411-418.
Patrizia, D.A.; Carbone, P.; Barraja, G.; Kelter, H.H.; Fiebig, G.; Cirrincione, G. Synthesis and antitumor activity of 2,5-bis(3′-indolyl)-furans and 3,5-bis(3′-indolyl)-isoxazoles, nortopsentin analogues. Bioorg. Med. Chem., 2010, 18, 4524-4529.
Padmaja, A.; Rajasekhar, C.; Muralikrishna, A.; Padmavathi, V. Synthesis and antioxidant activity of oxazolyl/thiazolylsulfonyl-methyl pyrazoles and isoxazoles. Eur. J. Med. Chem., 2011, 46, 5034-5038.
Prashanthi, Y.; Kiranmai, K.; Subhashini, N.J.P. Shivaraj, Synthesis, potentiometric and antimicrobial studies on metal complexes of isoxazole Schiff bases. Spectrochim. Acta A, 2008, 70, 5-30.
Talley, J.J.; Brown, D.L.; Carter, J.S.; Graneto, M.J.; Koboldt, C.M.; Masferrer, J.L.; Perkins, W.E.; Rogers, R.S.; Shaffer, A.F.; Zhang, Y.Y.; Zweifel, B.S.; Seiber, T.K. 4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, Valdecoxib: A Potent and Selective Inhibitor of COX-2. J. Med. Chem., 2000, 43, 775-777.
Karabasanagouda, T.; Adhikari, A.V.; Girisha, M. Synthesis of some new pyrazolines and isoxazoles carrying 4-methylthiophenyl moiety as potential analgesic and anti-inflammatory agents. Indian J. Chem., 2009, 48B, 430-437.
Lee, Y.S.; Park, S.M.; Kim, B.H. Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses. Bioorg. Med. Chem. Lett., 2009, 19, 1126-1128.
Changtam, C.; Hongmanee, P.; Suksamrarn, A. Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. Eur. J. Med. Chem., 2010, 45, 4446-4457.
Liu, Q.; Hou, X. One-Pot Three-Component Synthesis of 3-Methyl-4-Arylmethylene- Isoxazol-5(4H)- Ones Catalyzed by Sodium Sulfide. Phosphorus Sulfur Silicon Relat. Elem., 2012, 187, 448-453.
Mirzazadeh, M.; Mahdavinia, G.H. Fast and efficient synthesis of 4-arylidene-3-phenylisoxazol-5-ones. E-J. Chem., 2012, 9, 425-429.
Fozooni, S.; Hosseinzadeh, N.G.; Hamidian, H.; Akhgar, M.R. Nano Fe2O3, clinoptilolite and H3PW12O40 as efficient catalysts for solvent-free synthesis of 5(4H)-Isoxazolone under microwave irradiation conditions. J. Braz. Chem. Soc., 2013, 10, 1649-1655.
Saikh, F.; Das, J.; Ghosh, S. Synthesis of 3-methyl-4-arylmethylene isoxazole-5(4H)-ones by visible light in aqueous ethanol. Tetrahedron Lett., 2013, 54, 4679-4682.
Kiyani, H.; Ghorbani, F. Potassium phthalimide as efficient basic organocatalyst for the synthesis of 3,4-disubstituted isoxazol-5(4H)-ones in aqueous medium. J. Saudi Chem. Soc., 2017, 21, S112-S119.
Pourmousavi, S.A.; Fattahi, H.R.; Ghorbani, F. A green and efficient synthesis of isoxazol-5(4H)-one derivatives in water and a DFT study. J. IRAN Chem. Soc., 2018, 15, 455-469.
Navid, I.G.; Zare, A.; Sajadikhah, S.S.; Banaei, A. A novel dicationic ionic liquid as a highly effectual and Dual-functional catalyst for the synthesis of 3-methyl-4-arylmethylene-isoxazole-5(4H)-ones. Res. Chem. Intermed., 2018, 44, 6253-6266.
Dekamin, M.G.; Peyman, S.Z. Phthalimide-N-oxyl salts: efficient organocatalysts for facile synthesis of (Z)-3-methyl-4-(arylmethylene)- isoxazole-5(4H)-onederivatives in water. Monatshefte fuer Chemie., 2016, 147, 445-450.
Kolsepatil, S.R.; Nayana, P.; Lingampalle, D. An efficient monosodium glutamate (MSG) catalyzed multicomponent synthesis of isoxazolone in water under microwave irradiation. Der Pharma Chemica., 2017, 9, 52-55.
Patil, M.; Mudaliar, S.C.; Chaturbhuj, G.U. Sulfated polyborate catalyzed expeditious and efficient three-component synthesis of 3-methyl-4-(hetero) arylmethylene isoxazole-5(4H)-ones. Tetrahedron Lett., 2017, 58, 3256-3261.
Imène, A.K.; Raouf, B. Taous, B.; Boudjemaa, B.; Abdelmadjid, D. NaH2PO4 catalyzed a three- component 4-arylidene-3-methylisoxazol-5(4H)-ones synthesis in solvent-free conditions. Pharma Chemica., 2016, 8, 97-101.
Kiyani, H.; Ghorbani, F. Boric acid-catalyzed multi-component reaction for efficient synthesis of 4H-isoxazol5-ones in aqueous medium. Res. Chem. Intermed., 2015, 41, 2653-2664.
Surya, N.M.; Suresh, M.; Werner, E.V.; Sreekantha, B.J. Ag/SiO2 as a recyclable catalyst for the Facile green synthesis of 3-methyl-4(phenyl)methylene-isoxazole-5(4H)-ones. Res. Chem. Intermed., 2016, 42, 2553-2566.
Thopate, S.R.; Thorat, N.M. Natural organic acids promoted synthesis of 3, 4-dihydropyrimidin-2(1H) ones/thiones under solvent-free conditions. Lett. Org. Chem., 2015, 12, 210-216.
Thopate, S.R.; Kasar, S.B. Synthesis of Bis(indolyl)methanes using naturally occurring, Biodegradable itaconic acid as a green and reusable catalyst. Curr. Org. Synth., 2018, 15, 110-115.
Vakariya, R.H.; Patel, H.D. Facial ecofriendly and one pot synthesis of 3,4 disubstituted isoxazole-5(4H-one) using starch solution as a reaction media. Indian J. Chem., 2017, 56B, 890-896.

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