Synthesis of Arylmethylidene-isoxazol-5(4H)-ones via Three-Component Reaction in Water Catalyzed by Sodium Tetraborate

A series of arylmethylidene-isoxazol-5(4H)-ones have been prepared via a one-pot, three-component cyclocondensation process between aromatic aldehydes, ethyl acetoacetate, and hydroxylamine hydrochloride in good yields. It was found that sodium tetraborate to be an efficient and reusable catalyst for this condensation reaction under aqueous conditions at room temperature. Mild conditions, green, safe, shorter reaction times, eco-friendly, no use of organic solvent, and easy work-up of the products are remarkable advantages of this process.

[1]  H. Kiyani Synthesis of 4-arylmethylidene-3-methyl-isoxazol-5(4H)-ones via a three-component reaction in water catalyzed by sodium ascorbate , 2013 .

[2]  Suman Gupta,et al.  Chemotherapy of leishmaniasis. Part XI: synthesis and bioevaluation of novel isoxazole containing heteroretinoid and its amide derivatives. , 2012, Bioorganic & Medicinal Chemistry Letters.

[3]  Yunyun Liu,et al.  Recent advances in new multicomponent synthesis of structurally diversified 1,4-dihydropyridines , 2012 .

[4]  Yanlong Gu Multicomponent reactions in unconventional solvents: state of the art , 2012 .

[5]  Wei Wang,et al.  Chemistry and biology of multicomponent reactions. , 2012, Chemical reviews.

[6]  Sushobhan Chowdhury,et al.  Recent developments in solvent-free multicomponent reactions: a perfect synergy for eco-compatible organic synthesis , 2012 .

[7]  I. H. Bechtold,et al.  Synthesis and thermal behavior of new liquid crystals arylaldoxime esters , 2012 .

[8]  R. Orru,et al.  Recent developments in asymmetric multicomponent reactions. , 2012, Chemical Society reviews.

[9]  Keyume Ablajan,et al.  Efficient One-Pot Synthesis of β-Unsaturated Isoxazol-5-ones and Pyrazol-5-ones Under Ultrasonic Irradiation , 2012 .

[10]  Lanying Wang,et al.  Merocyanine dyes containing an isoxazolone nucleus: Synthesis, X-ray crystal structures, spectroscopic properties and DFT studies , 2012 .

[11]  T. Coviello,et al.  Evaluation of Rheological Properties and Swelling Behaviour of Sonicated Scleroglucan Samples , 2012, Molecules.

[12]  Qing Liu,et al.  One-Pot Three-Component Synthesis of 3-Methyl-4-Arylmethylene- Isoxazol-5(4H)- Ones Catalyzed by Sodium Sulfide , 2012 .

[13]  Hyeongjin Cho,et al.  Isoxazolone Derivatives as Potent Inhibitors of PTP1B , 2012 .

[14]  G. H. Mahdavinia,et al.  Fast and Efficient Synthesis of 4-Arylidene-3-phenylisoxazol-5-ones , 2012 .

[15]  M. A. Nassar,et al.  Effect of Addition of Boric Acid and Borax on Fire-Retardant and Mechanical Properties of Urea Formaldehyde Saw Dust Composites , 2011 .

[16]  Ya-nan Zhang,et al.  One-pot Synthesis of 3-Methyl-4-arylmethylene-isoxazol-5(4H)-ones Catalyzed by Sodium Benzoate in Aqueous Media: A Green Chemistry Strategy , 2011 .

[17]  R. Wu,et al.  Facile Synthesis of 3-Methyl-4-Arylmethylene-Isoxazol-5(4H)-Ones Catalysed by Sodium Silicate in an Aqueous Medium , 2011 .

[18]  V. Padmavathi,et al.  Synthesis and antioxidant activity of oxazolyl/thiazolylsulfonylmethyl pyrazoles and isoxazoles. , 2011, European journal of medicinal chemistry.

[19]  Guigen Li,et al.  New multicomponent cyclization: domino synthesis of pentasubstituted pyridines under solvent-free conditions. , 2011, Organic & biomolecular chemistry.

[20]  Gaohong Zhai,et al.  Synthesis and structural studies of 4-[(5-methoxy-1H-indole-3-yl)-methylene]-3-methyl-isoxazole-5-one by X-ray crystallography, NMR spectroscopy, and DFT calculations , 2011 .

[21]  Shouzhi Pu,et al.  Synthesis and the effects of substitution upon photochromic diarylethenes bearing an isoxazole moiety , 2011 .

[22]  Keyume Ablajan,et al.  The convenient synthesis of 4-arylmethylidene-4,5- dihydro-3-phenylisoxazol-5-ones , 2011 .

[23]  Thokhir Basha Shaik,et al.  Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents. , 2011, European journal of medicinal chemistry.

[24]  A. Suksamrarn,et al.  Isoxazole analogs of curcuminoids with highly potent multidrug-resistant antimycobacterial activity. , 2010, European journal of medicinal chemistry.

[25]  J. Nath,et al.  Borax: An Ecofriendly and Efficient Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones under Solvent-Free Conditions , 2010 .

[26]  Laura Sola,et al.  Design and synthesis of novel isoxazole-based HDAC inhibitors. , 2010, European journal of medicinal chemistry.

[27]  H. Fiebig,et al.  Synthesis and antitumor activity of 2,5-bis(3'-indolyl)-furans and 3,5-bis(3'-indolyl)-isoxazoles, nortopsentin analogues. , 2010, Bioorganic & medicinal chemistry.

[28]  C. S. Reddy,et al.  Synthesis and in vitro study of methylene-bis-tetrahydro[1,3]thiazolo[4,5-c]isoxazoles as potential nematicidal agents. , 2010, European journal of medicinal chemistry.

[29]  S. Franzblau,et al.  Synthesis and antituberculosis activity of novel mefloquine-isoxazole carboxylic esters as prodrugs. , 2010, Bioorganic & medicinal chemistry letters.

[30]  Maria M. M. Santos,et al.  Reaction of naphthoquinones with substituted nitromethanes. Facile synthesis and antifungal activity of naphtho[2,3-d]isoxazole-4,9-diones. , 2010, Bioorganic & medicinal chemistry letters.

[31]  K. Vasuki Multi-Component Reactions in Water , 2009 .

[32]  V. Padmavathi,et al.  Synthesis, antimicrobial and antioxidant activities of substituted pyrazoles, isoxazoles, pyrimidine and thioxopyrimidine derivatives. , 2009, European journal of medicinal chemistry.

[33]  Y. Nageswar,et al.  Multicomponent Approach Towards the Synthesis of Substituted Pyrroles under Supramolecular Catalysis Using β‐Cyclodextrin as a Catalyst in Water Under Neutral Conditions , 2009 .

[34]  Shouzhi Pu,et al.  Photochromism of new unsymmetrical isomeric diarylethenes bearing a pyridine group , 2009 .

[35]  A. V. Adhikari,et al.  Synthesis of Some New Pyrazolines (IV) and Isoxazoles (V) Carrying 4-Methylthiophenyl Moiety as Potential Analgesic and Antiinflammatory Agents. , 2009 .

[36]  S. Kartal,et al.  Termite Resistance of MDF Panels Treated with Various Boron Compounds , 2009, International Journal of Molecular Sciences.

[37]  M. Syamala,et al.  Recent Progress in Three-Component Reactions. An Update , 2009 .

[38]  B. Kim,et al.  Synthesis of 5-isoxazol-5-yl-2′-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses , 2008, Bioorganic & Medicinal Chemistry Letters.

[39]  Peng‐Fei Xu,et al.  Borax-catalyzed thiolysis of 1,2-epoxides in aqueous medium , 2008 .

[40]  Shivaraj,et al.  Synthesis, potentiometric and antimicrobial studies on metal complexes of isoxazole Schiff bases. , 2008, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[41]  U. Westermark,et al.  Effects of borate impregnation on the response of wood strength to heat treatment , 2005, Wood Science and Technology.

[42]  M. Yus,et al.  Asymmetric multicomponent reactions (AMCRs): the new frontier. , 2005, Angewandte Chemie.

[43]  C. Ghelardini,et al.  [(3-Chlorophenyl)piperazinylpropyl]pyridazinones and analogues as potent antinociceptive agents. , 2003, Journal of medicinal chemistry.

[44]  I. Ugi Recent progress in the chemistry of multicomponent reactions , 2001 .

[45]  R. S. Rogers,et al.  4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, valdecoxib: a potent and selective inhibitor of COX-2. , 2000, Journal of medicinal chemistry.

[46]  A. Sharifi,et al.  SOLID PHASE SYNTHESIS OF ISOXAZOLE AND PYRAZOLE DERIVATIVES UNDER MICROWAVE IRRADIATION , 2000 .

[47]  W. Knecht,et al.  Species-related inhibition of human and rat dihydroorotate dehydrogenase by immunosuppressive isoxazol and cinchoninic acid derivatives. , 1998, Biochemical pharmacology.

[48]  J. Yadav,et al.  A Convenient Synthesis of Benzopyranacetylenes , 1998 .

[49]  J. E. Winandy,et al.  Effects of fire retardant retention, borate buffers, and redrying temperature after treatment on thermal-induced degradation , 1997 .

[50]  C. Pande,et al.  Phase Transfer Catalyzed Oxidation of Ketones with Borax‐H2O2. , 1995 .

[51]  C. Pande,et al.  Phase transfer catalyzed oxidation of ketones with borax-H2O2 , 1995 .

[52]  R. Kido,et al.  Isoxazoles. XVIII. Synthesis and Pharmacological Properties of 5-Aminoalkyl- and 3-Aminoalkylisoxazoles and Related Derivatives. , 1967, Journal of medicinal chemistry.