239
Views
1
CrossRef citations to date
0
Altmetric
Research Articles

Lipase Catalyzed One-Pot Synthesis of 3-Methyl-4-(Hetero) Arylmethyleneisoxazole-5(4H)-Ones under Aqueous Conditions

ORCID Icon, ORCID Icon & ORCID Icon
Pages 4856-4865 | Received 07 Feb 2022, Accepted 20 Jun 2022, Published online: 14 Jul 2022

References

  • H. Ikeda, T. Sugiyama, and A. Ueno, “New Chemosensory for Larger Guests Based on Modified Cyclodextrin Bearing Seven Hydrophobic Chains Each with a Hydrophilic End Group,” Journal of Inclusion Phenomena and Macrocyclic Chemistry 57, no. 1–4 (2007): 83–7. nodoi:10.1007/s10847-006-9215-x.
  • M. N. Roy, M. C. Roy, and K. Roy, “Investigation of an Inclusion Complex Formed by Ionic Liquid and β-Cyclodextrin through Hydrophilic and Hydrophobic Interactions,” RSC Advances 5, no. 70 (2015): 56717–23. doi:10.1039/C5RA09823H.
  • F. Cavalieri, A. E. Hamassi, E. Chiessi, G. Paradossi, R. Villa, and N. Zaffaroni, “Tethering Functional Ligands onto Shell of Ultrasound Active Polymeric Microbubbles,” Biomacromolecules 7, no. 2 (2006): 604–11. doi:10.1021/bm050723g.
  • T. Ishioka, A. Kubo, Y. Koiso, K. Nagasawa, A. Itai, and Y. Hashimoto, “Novel Non-Steroidal/Non-Anilide Type Androgen Antagonists with an Isoxazolone Moiety,” Bioorganic & Medicinal Chemistry 10, no. 5 (2002): 1555–66. doi:10.1016/S0968-0896(01)00421-7.
  • G. H. C. Oliveira, L. M. Ramos, R. K. C. de Paiva, S. T. A. Passos, M. M. Simões, F. Machado, J. R. Correa, and B. A. D. Neto, “Synthetic Enzyme-Catalyzed Multicomponent Reaction for Isoxazol-5 (4H)-One Syntheses, Their Properties and Biological Application; Why Should One Study Mechanisms?” Organic & Biomolecular Chemistry 19, no. 7 (2021): 1514–31. doi:10.1039/d0ob02114h.
  • G. K. Saidachary, P. Veera, D. Divya, A. Singh, U. Ramesh, B. Sridhar, and B. China. Raju, “Convenient One-Pot Synthesis, anti-Mycobacterial and Anticancer Activities of Novel Benzoxepinoisoxazolones and Pyrazolones,” European Journal of Medicinal Chemistry 76 (2014): 460–9. doi:10.1016/j.ejmech.2014.02.042.
  • K. Bhooshan, N. G. Aher, D. Khadka, H. Park, and H. Cho, “Isoxazol-5 (4H) One Derivatives as PTP1B Inhibitors Showing an Anti-obesity Effect,” Chemistry, An Asian Journal 6, no. 8 (2011): 2073–9. doi:10.1002/asia.201100154.
  • M. Krzysztof, S. Kucharski, E. Ortyl, J.-M. Nunzi, S. Ahmadi-Kandjani, S. Dabos-Seignon, Siu-Wai. Chan, and R. Barille, “Second Harmonic Generation and Photochromic Grating in Polyurethane Films Containing Diazo Isoxazole Chromophore,” Optical Materials 30, no. 12 (2008): 1832–9. doi:10.1016/j.optmat.2007.11.030.
  • N. Irannejad-Gheshlaghchaei, A. Zare, S. S. Sajadikhah, and A. Banaei, “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,” Research on Chemical Intermediates 44, no. 10 (2018): 6253–66. doi:10.1007/s11164-018-3488-8.
  • H. Kiyani, and F. Ghorbani, “Boric Acid-Catalyzed Multi-Component Reaction for Efficient Synthesis of 4H-Isoxazol-5-Ones in Aqueous Medium,” Research on Chemical Intermediates 41, no. 5 (2015): 2653–64. doi:10.1007/s11164-013-1411-x.
  • S. S. Kapale, H. K. Chaudhari, S. N. Mali, B. S. Takale, and H. Pawar, “A Sustainable Approach towards the Three-Component Synthesis of Unsubstituted 1 H-Imidazoles in the Water at Ambient Conditions,” Journal of Asian Natural Products Research 23, no. 7 (2021): 712–16. doi:10.1080/10286020.2020.1760852.
  • S. A. Pourmousavi, H. R. Fattahi, F. Ghorbani, A. Kanaani, and D. Ajloo, “A Green and Efficient Synthesis of Isoxazol-5 (4H)-One Derivatives in Water and a DFT Study,” Journal of the Iranian Chemical Society 15, no. 2 (2018): 455–69. nodoi:10.1007/s13738-017-1246-2.
  • P. S. Manisha, C. Mudaliar, and G. U. Chaturbhuj, “Sulfated Polyborate Catalyzed Expeditious and Efficient Three-Component Synthesis of 3-Methyl-4-(Hetero) Arylmethylene Isoxazole-5 (4H)-Ones,” Tetrahedron Letters 58, no. 33 (2017): 3256–61. doi:10.1016/j.tetlet.2017.07.019.
  • S. N. Maddila, S. Maddila, W. E. van Zyl, and S. B. Jonnalagadda, “Ag/SiO2 as a Recyclable Catalyst for the Facile Green Synthesis of 3-Methyl-4-(Phenyl) Methylene-Isoxazole-5 (4H)-Ones,” Research on Chemical Intermediates 42, no. 3 (2016): 2553–66. doi:10.1007/s11164-015-2167-2.
  • H. Kiyani, and F. Ghorbani, “Expeditious Green Synthesis of 3, 4-Disubstituted Isoxazole-5 (4H)-Ones Catalyzed by nano-MgO,” Research on Chemical Intermediates 42, no. 9 (2016): 6831–44. doi:10.1007/s11164-016-2498-7.
  • A. S. Khedmatgozar, G. Aleaba, N. Daneshvar, and F. Shirini, “Sustainable and Green Synthesis of 3-Methyl-4-Arylmethylene-Isoxazole-5 (4H)-One Derivatives under Mild Conditions Using a Novel Phosphoric Acid-Based Molten Salt as Catalyst,” Sustainable Chemistry and Pharmacy 21 (2021): 100442. doi:10.1016/j.scp.2021.100442.
  • F. Saikh, J. Das, and S. Ghosh, “Synthesis of 3-Methyl-4-Arylmethylene Isoxazole-5 (4H)-Ones by Visible Light in Aqueous Ethanol,” Tetrahedron Letters 54, no. 35 (2013): 4679–82. doi:10.1016/j.tetlet.2013.06.086.
  • S. M. Srinivasa Budagumpi, J. G. Małecki, and R. S. Keri, “Green Synthesis of 3, 4-Disubstituted Isoxazol-(4H)-Ones Using ZnO@ Fe3O4 Core-Shell Nanocatalyst in Water,” Applied Organometallic Chemistry 34, no. 4 (2020): e5544.
  • F. Ghorbani, H. Kiyani, and S. A. Pourmousavi, “Facile and Expedient Synthesis of α, β-Unsaturated Isoxazol-5 (4H)-Ones under Mild Conditions,” Research on Chemical Intermediates 46, no. 1 (2020): 943–59. doi:10.1007/s11164-019-03999-7.
  • H. Kiyani, and A. Mosallanezhad, “Sulfanilic Acid-Catalyzed Synthesis of 4-Arylidene-3-Substituted Isoxazole-5 (4H)-Ones,” Current Organic Synthesis 15, no. 5 (2018): 715–22. doi:10.2174/1570179415666180423150259.
  • N. Reihani, and H. Kiyani, “Three-Component Synthesis of 4-Arylidene-3-Alkylisoxazol-5 (4H)-Ones in the Presence of Potassium 2,5-Dioxoimidazolidin-1-Ide,” Current Organic Chemistry 25, no. 8 (2021): 950–62. doi:10.2174/1385272825666210212120517.
  • F. K. Damghani, H. Kiyani, and S. A. Pourmousavi, “Green Three-Component Synthesis of Merocyanin Dyes Based on 4-Arylideneisoxazol-5 (4H)-Ones,” Current Green Chemistry 7, no. 2 (2020): 217–725. doi:10.2174/2213346107666200122093906.
  • M. Asiyeh, and H. Kiyani, “KI-Mediated Three-Component Reaction of Hydroxylamine Hydrochloride with Aryl/Heteroaryl Aldehydes and Two β-Oxoesters,” Orbital: The Electronic Journal of Chemistry 10, no. 2 (2018): 133–9. doi:10.17807/orbital.v10i2.1134.
  • H. Kiyani, and H. A. Samimi, “Nickel-Catalyzed One-Pot, Three-Component Synthesis of 3, 4-Disubstituted Isoxazole-5 (4H)-Ones in Aqueous Medium,” Chiang Mai Journal of Science 44, no. 3 (2017): 1011–21.
  • Z. Faramarzi, and H. Kiyani, “Organocatalyzed Three-Component Synthesis of Isoxazol-5 (4H)-Ones under Aqueous Conditions,” Heterocycles 102, no. 9 (2021): 1779–90. doi:10.3987/COM-21-14488.
  • S. R. Deshmukh, A. S. Nalkar, and S. R. Thopate, “Pyruvic Acid-Catalyzed One-Pot Three-Component Green Synthesis of Isoxazoles in Aqueous Medium: A Comparable Study of Conventional Heating versus Ultra-Sonication,” Journal of Chemical Sciences 134, no. 1 (2022): 1. doi:10.1007/s12039-021-02016-y.
  • H. Kiyani, and F. Ghorbani, “Efficient Tandem Synthesis of a Variety of Pyran-Annulated Heterocycles, 3, 4-Disubstituted Isoxazol-5 (4H)-Ones, and α, β-Unsaturated Nitriles Catalyzed by Potassium Hydrogen Phthalate in Water,” Research on Chemical Intermediates 41, no. 10 (2015): 7847–7882. doi:10.1007/s11164-014-1863-7.
  • Z. Faramarzi, and H. Kiyani, “Steglich’s Base Catalyzed Three-Component Synthesis of Isoxazol-5-Ones,” Polycyclic Aromatic Compounds 4 (2022): 1–23. doi:10.1080/10406638.2022.2061533.
  • A. Mosallanezhad, and H. Kiyani, “Green Synthesis of 3-Substituted-4-Arylmethylideneisoxazol-5 (4H)-One Derivatives Catalyzed by Salicylic Acid,” Current Organocatalysis 6, no. 1 (2019): 28–35. doi:10.2174/2213337206666190214161332.
  • H. Kiyani, H. Darbandi, A. Mosallanezhad, and F. Ghorbani, “2-Hydroxy-5-Sulfobenzoic Acid: An Efficient Organocatalyst for the Three-Component Synthesis of 1-Amidoalkyl-2-Naphthols and 3, 4-Disubstituted Isoxazol-5 (4H)-Ones,” Research on Chemical Intermediates 41, no. 10 (2015): 7561–7579. doi:10.1007/s11164-014-1844-x.
  • A. B. Rikani, and D. Setamdideh, “One-Pot and Three-Component Synthesis of Isoxazol-5 (4H)-One Derivatives in the Presence of Citric Acid,” Oriental Journal of Chemistry 32, no. 3 (2016): 1433–1437. doi:10.13005/ojc/320317.
  • R. Laroum, and A. Debache, “New Eco-Friendly Procedure for the Synthesis of 4-Arylmethylene-Isoxazol-5 (4H)-Ones Catalyzed by Pyridinium p-Toluenesulfonate (PPTS) in Aqueous Medium,” Synthetic Communications 48, no. 14 (2018): 1876–1882. doi:10.1080/00397911.2018.1473440.
  • M. Behrooz, M. Chahkandi, R. Tayebee, S. Kahrobaei, H. Alinezhad, and S. Hemmati, “Synthesis and Characterization of Nanocrystalline Hydroxyapatite and Its Catalytic Behavior towards Synthesis of 3, 4-Disubstituted Isoxazole-5 (4H)-Ones in Water,” Applied Organometallic Chemistry 33, no. 10 (2019): e5118. doi:10.1002/aoc.5118.
  • Parteek Kour, Monika Ahuja, Pratibha Sharma, Ashok Kumar, and Anil Kumar, “An Improved Protocol for the Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-Ones through L-Valine-Mediated Domino Three-Component Strategy,” Journal of Chemical Sciences 132, no. 1 (2020): 108. doi:10.1007/s12039-020-01801-5.
  • N. T. Hatvate, and S. M. Ghodse, “One-Pot Three-Component Synthesis of Isoxazole Using ZSM-5 as a Heterogeneous Catalyst,” Synthetic Communications 50, no. 23 (2020): 3676–83. doi:10.1080/00397911.2020.1815786.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.