One-Pot Multicomponent Synthesis of 3-Methyl-4-(Hetero)Arylmethylene Isoxazole-5(4H)-Ones Using Guanidine Hydrochloride as the Catalyst under Aqueous Conditions

References

• 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.
   Web of Science ®Google Scholar
• M. Shanshak, Srinivasa Budagumpi, Jan Grzegorz Małecki, and Rangappa S. Keri, “Green Synthesis of 3,4‐Disubstituted Isoxazol‐5(4H)‐Ones Using ZnO@Fe3O4 Core–Shell Nanocatalyst in Water,” Applied Organometallic Chemistry 34, no. 4 (2020): 5544.
   Web of Science ®Google Scholar
• F. Noruzian, A. Olyaei, R. Hajinasiri, and M. Sadeghpour, “Guanidine Hydrochloride Catalyzed Efficient One-Pot Pseudo Five-Component Synthesis of 4,4′-(Arylmethylene)Bis(1H-Pyrazol-5-Ols) in Water,” Synthetic Communications 49, no. 20 (2019): 2717–24.
   Web of Science ®Google Scholar
• Y. U. Gadkari, N. L. Jadhav, N. T. Hatvate, and V. N. Telvekar, “Concentrated Solar Radiation Aided Green Approach for Preparative Scale and Solvent‐Free Synthesis of 3‐Methyl‐4‐(Hetero)Arylmethylene Isoxazole‐5(4H)‐Ones,” ChemistrySelect 5, no. 39 (2020): 12320–3.
   Web of Science ®Google Scholar
• H. Atharifar, A. Keivanloo, and B. Maleki, “Greener Synthesis of 3,4-Disubstituted Isoxazole-5(4H)-Ones in a Deep Eutectic Solvent,” Organic Preparations and Procedures International 52, no. 6 (2020): 517–23.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• K. Tanaka, and F. Toda, “Solvent-Free Organic Synthesis,” Chemical Reviews 100, no. 3 (2000): 1025–74.
   PubMed Web of Science ®Google Scholar
• A. Mosallanezhad, 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.
   Web of Science ®Google Scholar
• T. Lohar, A. Kumbhar, M. Barge, and R. Salunkhe, “DABCO Functionalized Dicationic Ionic Liquid (DDIL): A Novel Green Benchmark in Multicomponent Synthesis of Heterocyclic Scaffolds under Sustainable Reaction Conditions,” Journal of Molecular Liquids 224, (2016): 1102–8.
   Web of Science ®Google Scholar
• K. Naka, E. Horii, and Y. Chujo, “Synthesis and Optical Properties of Soluble Isoxazole-Containing Poly(p-Phenylene)-Related Polymer,” Polymer Journal 32, no. 1 (2000): 73–4.
   Web of Science ®Google Scholar
• G. D. Vilela, Rosa, R.R. da Rosa and A. A. Merlo, “Isoxazole Derivatives With Potential Applications in Polymers and Semiconductors.,” in Proceedings of the 14th Brazilian Meeting on Organic Synthesis Proceedings (14th Brazilian Meeting on Organic Synthesis, Brasilia, Brasil: Editora Edgard Blücher), (2013): 32–32.
   Google Scholar
• D. N. Tomilin, L. N. Sobenina, K. B. Petrushenko, I. A. Ushakov, and B. A. Trofimov, “Design of Novel Meso-CF3-BODIPY Dyes with Isoxazole Substituents,” Dyes and Pigments 152, (2018): 14–8.
   Web of Science ®Google Scholar
• H. Ball, Ch D. Marciniak, R. N. Wolf, A. T.-H. Hung, K. Pyka, and M. J. Biercuk, “Synthesis of New Liquid Crystalline Isoxazole‐, Pyrazole‐ and 2‐Isoxazoline‐Containing Compounds,” The Review of Scientific Instruments 90, no. 5 (2019): 053103–27.
   PubMedGoogle Scholar
• P. Vitale, and A. Scilimati, “Recent Developments in the Chemistry of 3-Arylisoxazoles and 3-Aryl-2-Isoxazolines,” Advances in Heterocyclic Chemistry 122, (2017): 1–41.
   Web of Science ®Google Scholar
• X. H. Zhang, Y. H. Zhan, D. Chen, F. Wang, and L. Wang, “Merocyanine Dyes Containing an Isoxazolone Nucleus: Synthesis, X-Ray Crystal Structures, Spectroscopic Properties and DFT Studies,” Dyes and Pigments 93, no. 1–3 (2012): 1408–15.
   Web of Science ®Google Scholar
• P. Diana, A. Carbone, P. Barraja, G. Kelter, H. H. Fiebig, and G. Cirrincione, “Synthesis and Antitumor Activity of 2,5-bis(3′-indolyl)-furans and 3,5-bis(3'-indolyl)-isoxazoles, nortopsentin analogues,” Bioorganic & Medicinal Chemistry 18, no. 12 (2010): 4524–9. [PMC][10.1016/j.bmc.2010.04.061] [20472437]
   PubMed Web of Science ®Google Scholar
• M. M. M. Santos, N. Faria, J. Iley, S. J. Coles, M. B. Hursthouse, M. L. Martins, and R. Moreira, “Reaction of Naphthoquinones with Substituted Nitromethanes. Facile Synthesis and Antifungal Activity of Naphtho[2,3-d]Isoxazole-4,9-Diones,” Bioorganic & Medicinal Chemistry Letters 20, no. 1 (2010): 193–5.
   PubMed Web of Science ®Google Scholar
• H. Beyzaei, M. Kamali Deljoo, R. Aryan, B. Ghasemi, M. M. Zahedi, and M. Moghaddam-Manesh, “Green Multicomponent Synthesis, Antimicrobial and Antioxidant Evaluation of Novel 5-Amino-Isoxazole-4-Carbonitriles,” Chemistry Central Journal 12, no. 1 (2018): 114
   PubMedGoogle Scholar
• Y. K. Kang, K. J. Shin, K. H. Yoo, K. J. Seo, C. Y. Hong, C.-S. Lee, S. Y. Park, D. J. Kim, and S. W. Park, “Synthesis and Antibacterial Activity of New Carbapenems Containing Isoxazole Moiety,” Bioorganic & Medicinal Chemistry Letters 10, no. 2 (2000): 95–9.
   PubMed Web of Science ®Google Scholar
• H. Kan Unk O, I. Adachi, R. Kido, and K. Hirose, “Isoxazoles. XVIII. Synthesis and Pharmacological Properties of 5-Aminoalkyl- and 3-Aminoalkylisoxazoles and Related Derivatives,” J Med Chem 10, no. 3 (1967): 411–8.
   PubMed Web of Science ®Google Scholar
• A. Padmaja, C. Rajasekhar, A. Muralikrishna, and V. Padmavathi, “Synthesis and Antioxidant Activity of Oxazolyl/Thiazolylsulfonylmethyl Pyrazoles and Isoxazoles,” European Journal of Medicinal Chemistry 46, no. 10 (2011): 5034–8.
   PubMed Web of Science ®Google Scholar
• R. Laroum, R. Boulcina, C. Bensouici, and A. Debache, “Facile Synthesis and Antioxidant Evaluation of 4-Arylmethylideneisoxazol-5(4H)-Ones,” Organic Preparations and Procedures International 51, no. 6 (2019): 583–8.
   Web of Science ®Google Scholar
• Bo-Liang Deng, Matthew D. Cullen, Zhigang Zhou, Tracy L. Hartman, Robert W. Buckheit, Christophe Pannecouque, Erik De Clercq, Phillip E. Fanwick, and Mark Cushman, “Synthesis and anti-HIV Activity of New Alkenyldiarylmethane (ADAM) Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs) Incorporating Benzoxazolone and Benzisoxazole Rings,” Bioorganic & Medicinal Chemistry 14, no. 7 (2006): 2366–74.
   PubMed Web of Science ®Google Scholar
• J. J. Talley, D. L. Brown, J. S. Carter, M. J. Graneto, C. M. Koboldt, J. L. Masferrer, W. E. Perkins, R. S. Rogers, A. F. Shaffer, Y. Y. Zhang, et al. “4-[5-Methyl-3-Phenylisoxazol-4-Yl]-Benzenesulfonamide, Valdecoxib: A Potent and Selective Inhibitor of COX-2,” Journal of Medicinal Chemistry 43, no. 5 (2000): 775–7.
   PubMed Web of Science ®Google Scholar
• D. G. Martin, C. G. Chidester, S. A. Mizsak, D. J. Duchamp, L. Baczynskyj, W. C. Krueger, R. J. Wnuk, and P. A. Meulman, “The Isolation, Structure, and Absolute Configuration of U-43,795, a New Antitumor Agent,” The Journal of Antibiotics 28, no. 1 (1975): 91–3. [PMC][10.7164/antibiotics.28.91] [1126872]
   PubMed Web of Science ®Google Scholar
• C. H. Stammer, A. N. Wilson, C. F. Spencer, F. W. Bachelor, F. W. Holly, and K. Folkers, “Synthesis of Cycloserine and a Methyl Analog,” Journal of the American Chemical Society 79, no. 12 (1957): 3236–40.
   Web of Science ®Google Scholar
• K. Bowden, G. Crank, and W. J. Ross, “The Synthesis of Pantherine and Related Compounds,” Journal of the Chemical Society C: Organic (1968) : 172–85.
   Google Scholar
• M. S. Patil, 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.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• M. Mashhadinezhad, F. Shirini, and M. Mamaghani, “Nanoporous Na+-Montmorillonite Perchloric Acid as an Efficient Heterogeneous Catalyst for Synthesis of Merocyanine Dyes Based on Isoxazolone and Barbituric Acid,” Microporous and Mesoporous Materials 262, (2018): 269–82.
   Web of Science ®Google Scholar
• M. G. Dekamin, and S. Z. Peyman, “Phthalimide-N-Oxyl Salts: Efficient Organocatalysts for Facile Synthesis of (Z)-3-Methyl-4-(Arylmethylene)-Isoxazole-5(4H)-One Derivatives in Water,” Monatshefte Für Chemie – Chemical Monthly 147, no. 2 (2016): 445–50.
   Google Scholar
• A. U. Khandebharad, S. R. Sarda, C. H. Gill, and B. R. Agrawal, “Synthesis of 3-Methyl-4-Arylmethylene-Isoxazol-5 (4H)-Ones Catalyzed by Tartaric Acid in Aqueous Media,” Research Journal of Chemical Sciences 5, no. 5 (2015): 1–5.
   Google Scholar
• 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): 7561–79.
   Web of Science ®Google Scholar
• H. Kiyani, A. Kanaani, D. Ajloo, F. Ghorbani, and M. Vakili, “N-Bromosuccinimide (NBS)-Promoted, Three-Component Synthesis of α,β-Unsaturated Isoxazol-5(4H)-Ones, and Spectroscopic Investigation and Computational Study of 3-Methyl-4-(Thiophen-2-Ylmethylene)Isoxazol-5(4H)-One,” Research on Chemical Intermediates 41, no. 10 (2015): 7739–73.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• A. Bashash 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): 1433–7.
   Web of Science ®Google Scholar
• J. Safari, M. Ahmadzadeh, and Z. Zarnegar, “Sonochemical Synthesis of 3-Methyl-4-Arylmethylene Isoxazole-5(4H)-Ones by Amine-Modified Montmorillonite Nanoclay,” Catalysis Communications 86, (2016): 91–5.
   Web of Science ®Google Scholar
• H. Kiyani, and F. Ghorbani, “Potassium Phthalimide as Efficient Basic Organocatalyst for the Synthesis of 3,4-Disubstituted Isoxazol-5(4H)-Ones in Aqueous Medium,” Journal of Saudi Chemical Society 21, (2017): S112–S19.
   Web of Science ®Google Scholar
• Pavol Štefík, Adriana Annušová, Boris Lakatoš, Katarína Elefantová, Lucia Čepcová, Monika Hofbauerová, Anna Kálosi, Matej Jergel, Eva Majkova, and Peter Siffalovic, “A Facile & Convenient Route for the Stereoselective Synthesis of Z- Isoxazol-5(4H)-Ones Derivatives Catalysed by Sodium Acetate: Synthesis, Multispectroscopic Properties, Crystal Structure with DFT Calculations, DNA-Binding Studies and Molecular Docking Studies,” Biomedical Materials (Bristol, England) 1200, (2021): 127067.
   Google Scholar
• 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.
   Web of Science ®Google Scholar
• Q. Liu, and Y. –N. Zhang, “One-Pot Synthesis of 3-Methyl-4-Arylmethylene-Isoxazol-5(4H)-Ones Catalyzed by Sodium Benzoate in Aqueous Media: A Green Chemistry Strategy,” Bulletin of the Korean Chemical Society 32, no. 10 (2011): 3559–60.
   Web of Science ®Google Scholar
• 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 J. Sci 44, no. 3 (2017): 1011–21.
   Web of Science ®Google Scholar
• G. D. Shirole, A. S. Tambe, and S. N. Shelke, “Ionic Liquid Catalyzed One Pot Green Synthesis of Isoxazolone Derivatives via Multicomponent Reaction,” Indian Journal of Chemistry 59B (2020) : 459–64.
   Google Scholar
• Z. Ye, L. Bai, Y. Bai, Z. Gan, H. Zhou, T. Pan, Y. Yu, and J. Zhou, “High Diastereoselective Synthesis of Spiro-Isoxazolonechromans via Domino Oxa-Michael/1,6-Addition Reactions of Ortho-Hydroxyphenylsubstituted Para-Quinone Methides with Unsaturated Isoxazolones,” Tetrahedron 75, no. 5 (2019): 682–7.
   Web of Science ®Google Scholar
• 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): 217–25.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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): 7847–82.
   Web of Science ®Google Scholar
• K. Ablajan, and H. Xiamuxi, “Efficient One-Pot Synthesis of β -Unsaturated Isoxazol-5-Ones and Pyrazol-5-Ones under Ultrasonic Irradiation,” Synthetic Communications 42, no. 8 (2012): 1128–36.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• P. Kulkarni, “An Efficient Solvent-Free Synthesis of 3,4-Disubstituted Isoxazole-5(4H)-Ones Using Microwave Irradiation,” Journal of the Indian Chemical Society 98, no. 1 (2021): 100013.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar
• F. Jahani, M. Tajbakhsh, H. Golchoubian, and S. Khaksar, “Guanidine Hydrochloride as an Organocatalyst for N-Boc Protection of Amino Groups,” Tetrahedron Letters 52, no. 12 (2011): 1260–4.
   Web of Science ®Google Scholar
• J. Xu, J. Liu, Z. Li, H. Wang, S. Xu, T. Guo, H. Zhu, F. Wei, Y. Zhu, and K. Guo, “Guanidinium as Bifunctional Organocatalyst for Ring-Opening Polymerizations,” Polymer 154, (2018): 17–26.
   Web of Science ®Google Scholar
• M. Sadeghpour, A. Olyaei, and M. Rezaei, “Guanidine Hydrochloride: A Highly Efficient Organocatalyst for the Synthesis of 12-Aryl-8,9,10,12-Tetrahydrobenzo [a] Xanthene-11-Ones under Solvent-Free Conditions: Synthesis of Xanthenones,” Journal of Heterocyclic Chemistry 53, no. 3 (2016): 981–8.
   Web of Science ®Google Scholar
• M. M. Heravi, M. Zakeri, and N. Mohammadi, “Guanidine Hydrochloride: An Active and Simple Catalyst for Mannich Type Reaction in Solvent-Free Condition,” Chinese Chemical Letters 22, no. 7 (2011): 797–800.
   Web of Science ®Google Scholar
• A. Heydari, A. Arefi, S. Khaksar, and R. K. Shiroodi, “Guanidine Hydrochloride: An Active and Simple Catalyst for Strecker Type Reaction,” Journal of Molecular Catalysis A: Chemical 271, no. 1-2 (2007): 142–4.
   Google Scholar
• A. H. Cahyana, B. Ardiansah, and N. R. Aisy, “An Efficient One-Pot Multicomponent Synthesis of 1,4-Dihydropyridines Catalyzed by Guanidine Hydrochloride,” IOP Conference Series: Materials Science and Engineering 763, (2020): 012048.
   Google Scholar
• A. Heydari, A. Arefi, S. Khaksar, and M. Tajbakhsh, “Hydrophosphonylation of Aldehydes Catalysed by Guanidine Hydrochloride in Water,” Catalysis Communications 7, no. 12 (2006): 982–4.
   Web of Science ®Google Scholar
• 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.
   Web of Science ®Google Scholar