Microwave-Assisted Chemistry: New Synthetic Application for the Rapid Construction of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives in Diisopropyl Ethyl Ammonium Acetate

References

• X. Yan, S. Anguille, M. Bendahan, and P. Moulin, “Ionic Liquids Combined with Membrane Separation Processes: A Review,” Separation and Purification Technology 222 (2019): 230–53.
   Web of Science ®Google Scholar
• M. A. P. Martins, C. P. Frizzo, D. N. Moreira, N. Zanatta, and H. G. Bonacorso, “Ionic Liquids in Heterocyclic Synthesis,” Chemical Reviews 108, no. 6 (2008): 2015–50.
   PubMed Web of Science ®Google Scholar
• N. Isambert, M. d. M. S. Duque, J.-C. Plaquevent, Y. Génisson, J. Rodriguez, and T. Constantieux, “Multicomponent Reactions and Ionic Liquids: A Perfect Synergy for Eco-Compatible Heterocyclic Synthesis,” Chemical Society Reviews 40, no. 3 (2011): 1347–57.
   PubMed Web of Science ®Google Scholar
• M. Petkovic, K. R. Seddon, L. P. N. Rebelo, and C. S. Pereira, “Ionic Liquids: A Pathway to Environmental Acceptability,” Chemical Society Reviews 40, no. 3 (2011): 1383–403.
   PubMed Web of Science ®Google Scholar
• C. Garkoti, J. Shabir, and S. Mozumdar, “Amine‐Terminated Ionic Liquid Modified Magnetic Graphene Oxide (MGO‐IL‐NH 2): A Highly Efficient and Reusable Nanocatalyst for the Synthesis of 3‐Amino Alkylated Indoles,” ChemistrySelect 5, no. 14 (2020): 4337–46.
   Web of Science ®Google Scholar
• S. S. Kamble and G. S. Shankarling, “An Effect of H-Bonding in Synthesis of 1, 5-Diketones via Tandem Aldol-Michael Addition Reaction Using Room Temperature Ionic Liquid (RTIL),” ChemistrySelect 2, no. 5 (2017): 1917–24.
   Web of Science ®Google Scholar
• B. Banerjee, “[Bmim]BF 4: A Versatile Ionic Liquid for the Synthesis of Diverse Bioactive Heterocycles,” ChemistrySelect 2, no. 27 (2017): 8362–76.
   Web of Science ®Google Scholar
• A. Vioux, L. Viau, S. Volland, and J. Le. Bideau, “Use of Ionic Liquids in Sol-Gel; Ionogels and Applications,” Comptes Rendus Chimie 13, no. 1–2 (2010): 242–55.
   Web of Science ®Google Scholar
• B. Sanay, B. Strehmel, and V. Strehmel, “Green Approach of Photoinitiated Polymerization Using Monomers Derived from Oleic Acid and Ionic Liquid,”ChemistrySelect 4, no. 35 (2019): 10214–8.
   Web of Science ®Google Scholar
• E. Gelens, F. J. J. De Kanter, R. F. Schmitz, L. A. J. M. Sliedregt, B. J. Van Steen, C. G. Kruse, R. Leurs, M. B. Groen, and R. V. A. Orru, “Efficient Library Synthesis of Imidazoles Using a Multicomponent Reaction and Microwave Irradiation,”Molecular Diversity 10, no. 1 (2006): 17–22.
   PubMed Web of Science ®Google Scholar
• M. Li, Z. Zuo, L. Wen, and S. Wang, “Microwave-Assisted Combinatorial Synthesis of Hexa-Substituted 1,4-Dihydropyridines Scaffolds Using One-Pot Two-Step Multicomponent Reaction Followed by a S-Alkylation,” Journal of Combinatorial Chemistry 10, no. 3 (2008): 436–41.
   PubMedGoogle Scholar
• J. Fairoosa, S. Saranya, S. Radhika, and G. Anilkumar, “Recent Advances in Microwave Assisted Multicomponent Reactions,”ChemistrySelect 5, no. 17 (2020): 5180–97.
   Web of Science ®Google Scholar
• B. M. Khadilkar and G. L. Rebeiro, “Microwave-Assisted Synthesis of Room-Temperature Ionic Liquid Precursor in Closed Vessel,” Organic Process Research & Development 6, no. 6 (2002): 826–8.
   Web of Science ®Google Scholar
• A. A. Saikia, R. Nishanth Rao, S. Das, S. Jena, S. Rej, B. Maiti, and K. Chanda, “Sequencing [3 + 2]-Cycloaddition and Multicomponent Reactions: A Regioselective Microwave-Assisted Synthesis of 1,4-Disubstituted 1,2,3-Triazoles Using Ionic Liquid Supported Cu(II) Precatalysts in Methanol,” Tetrahedron Letters 61, no. 36 (2020): 152273.
   Web of Science ®Google Scholar
• A. N. Dadhania, V. K. Patel, and D. K. Raval, “Ionic Liquid Promoted Facile and Green Synthesis of 1,8-Dioxo-Octahydroxanthene Derivatives under Microwave Irradiation,” Journal of Saudi Chemical Society 21 (2017): S163–S9.
   Web of Science ®Google Scholar
• M. Messali, “A Facile and Green Microwave-Assisted Synthesis of New Functionalized Picolinium-Based Ionic Liquids,” Arabian Journal of Chemistry 9 (2016): S564–S9.
   Web of Science ®Google Scholar
• Q. Zhu, H. Jiang, J. Li, M. Zhang, X. Wang, and C. Qi, “Practical Synthesis and Mechanistic Study of Polysubstituted Tetrahydropyrimidines with Use of Domino Multicomponent Reactions,” Tetrahedron 65, no. 23 (2009): 4604–13.
   Web of Science ®Google Scholar
• E. Ruijter, R. Scheffelaar, and R. V. A. Orru, “Multicomponent Reaction Design in the Quest for Molecular Complexity and Diversity,” Angewandte Chemie (International ed. in English) 50, no. 28 (2011): 6234–46.
   PubMed Web of Science ®Google Scholar
• L.-J. Yan and Y.-C. Wang, “Recent Advances in Green Synthesis of 3,3′-Spirooxindoles via Isatin-Based One-Pot Multicomponent Cascade Reactions in Aqueous Medium,” ChemistrySelect 1, no. 21 (2016): 6948–60.
   Web of Science ®Google Scholar
• R. C. Cioc, E. Ruijter, and R. V. A. Orru, “Multicomponent Reactions: advanced Tools for Sustainable Organic Synthesis,” Green Chemistry 16, no. 6 (2014): 2958–75.
   Web of Science ®Google Scholar
• O. V. Kharissova, B. I. Kharisov, C. M. Oliva González, Y. P. Méndez, and I. López, “Greener Synthesis of Chemical Compounds and Materials,” Royal Society Open Science 6, no. 11 (2019): 191378.
   PubMed Web of Science ®Google Scholar
• J.-C. Liu, S. Narva, K. Zhou, and W. Zhang, “A Review on the Antitumor Activity of Various Nitrogenous-Based Heterocyclic Compounds as NSCLC Inhibitors,” Mini Reviews in Medicinal Chemistry 19, no. 18 (2019): 1517–30.
   PubMed Web of Science ®Google Scholar
• S. Tahlan, S. Kumar, and B. Narasimhan, “Pharmacological Significance of Heterocyclic 1H-Benzimidazole Scaffolds: A Review,” BMC Chemistry 13, no. 1 (2019): 1–21.
   PubMed Web of Science ®Google Scholar
• S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappalà, G. Puja, M. Baraldi, and C. De Micheli, “Synthesis and Anticonvulsant Activity of Novel and Potent 6,7-methylenedioxyphthalazin-1(2H)-ones,” Journal of Medicinal Chemistry 43, no. 15 (2000): 2851–9.
   PubMed Web of Science ®Google Scholar
• S. N. Shalkouhi, H. Kefayati, and S. Shariati, “Synthesis of Novel Spiro[Chromeno[4′,3′:3,4]Pyrazolo[1,2-b]Phthalazine-7,3′-Indoline]-2′,6,9,14-Tetraone,” Journal of the Iranian Chemical Society 16, no. 2 (2019): 263–7.
   Web of Science ®Google Scholar
• N. Watanabe, Y. Kabasawa, Y. Takase, M. Matsukura, K. Miyazaki, H. Ishihara, K. Kodama, and H. Adachi, “4-Benzylamino-1-Chloro-6-Substituted Phthalazines: Synthesis and Inhibitory Activity toward Phosphodiesterase 5,” Journal of Medicinal Chemistry 41, no. 18 (1998): 3367–72.
   PubMed Web of Science ®Google Scholar
• V. A. Chebanov, E. A. Muravyova, S. M. Desenko, V. I. Musatov, I. V. Knyazeva, S. V. Shishkina, O. V. Shishkin, and C. O. Kappe, “Microwave-Assisted Three-Component Synthesis of 7-Aryl-2-Alkylthio-4,7-Dihydro-1,2,4-Triazolo[1,5-a]-Pyrimidine-6-Carboxamides and Their Selective Reduction,” Journal of Combinatorial Chemistry 8, no. 3 (2006): 427–34.
   PubMedGoogle Scholar
• J. S. Kim, H.-K. Rhee, H. J. Park, S. K. Lee, C.-O. Lee, and H.-Y. Park Choo, “Synthesis of 1-/2-Substituted-[1,2,3]Triazolo[4,5-g]Phthalazine-4,9-Diones and Evaluation of Their Cytotoxicity and Topoisomerase II Inhibition,” Bioorganic & Medicinal Chemistry 16, no. 8 (2008): 4545–50.
   PubMed Web of Science ®Google Scholar
• C.-K. Ryu, R.-E. Park, M.-Y. Ma, and J.-H. Nho, “Synthesis and Antifungal Activity of 6-Arylamino-Phthalazine-5,8-Diones and 6,7-Bis(Arylthio)-Phthalazine-5,8-Diones,” Bioorganic & Medicinal Chemistry Letters 17, no. 9 (2007): 2577–80.
   PubMed Web of Science ®Google Scholar
• C. B. Sangani, J. A. Makwana, Y.-T. Duan, N. J. Thumar, M.-Y. Zhao, Y. S. Patel, and H.-L. Zhu, “Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives: assessment of Their Antimicrobial, Antituberculosis and Antioxidant Activity,” Research on Chemical Intermediates 42, no. 3 (2016): 2101–17.
   Web of Science ®Google Scholar
• H. R. M. Rashdan, S. M. Gomha, M. S. El-Gendey, M. A. El-Hashash, and A. M. M. Soliman, “Eco-Friendly One-Pot Synthesis of Some New Pyrazolo[1,2-b] Phthalazinediones with Antiproliferative Efficacy on Human Hepatic Cancer Cell Lines,” Green Chemistry Letters and Reviews 11, no. 3 (2018): 264–74.
   Web of Science ®Google Scholar
• J. Sinkkonen, V. Ovcharenko, K. N. Zelenin, I. P. Bezhan, B. A. Chakchir, F. Al-Assar, and K. Pihlaja, “1H and 13C NMR Study of 1-Hydrazino-2,3-Dihydro-1H-Pyrazolo[1,2-a]Pyridazine-5,8-Diones and -1H-Pyrazolo[1,2-b]Phthalazine-5,10-Diones and Their Ring-Chain Tautomerism,” European Journal of Organic Chemistry 2002, no. 13 (2002): 2046.
   Web of Science ®Google Scholar
• Y. A. Tayade and D. S. Dalal, “β-Cyclodextrin as a Supramolecular Catalyst for the Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives in Water,” Catalysis Letters 147, no. 6 (2017): 1411–21.
   Web of Science ®Google Scholar
• R. Ghahremanzadeh, G. Shakibaei, and A. Bazgir, “An Efficient One-Pot Synthesis of 1 H-Pyrazolo[1,2-b] Phthalazine-5,10-Dione Derivatives,” Synlett 2008, no. 8 (2008): 1129–32.
   Web of Science ®Google Scholar
• F. Mohamadpour, M. T. Maghsoodlou, R. Heydari, and M. Lashkari, “Copper(II) Acetate Monohydrate: An Efficient and Eco-Friendly Catalyst for the One-Pot Multi-Component Synthesis of Biologically Active Spiropyrans and 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives under Solvent-Free Conditions,” Research on Chemical Intermediates 42, no. 12 (2016): 7841–53.
   Web of Science ®Google Scholar
• D. S. Raghuvanshi and K. N. Singh, “A Highly Efficient Green Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives and Their Photophysical Studies,” Tetrahedron Letters 52, no. 43 (2011): 5702–5.
   Web of Science ®Google Scholar
• A. Bashti, A. R. Kiasat, and B. Mokhtari, “Synthesis and Characterization of Dicationic 4,4′-Bipyridinium Dichloride Ordered Mesoporous Silica Nanocomposite and Its Application in the Preparation of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives,” RSC Advances 5, no. 33 (2015): 25816–23.
   Web of Science ®Google Scholar
• M. Veeranarayana Reddy and Y. T. Jeong, “InCl3-Catalyzed Green Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Diones under Solvent-Free Conditions,” Tetrahedron Letters 54, no. 27 (2013): 3546–9.
   Web of Science ®Google Scholar
• M. R. Nabid, S. J. T. Rezaei, R. Ghahremanzadeh, and A. Bazgir, “Ultrasound-Assisted One-Pot, Three-Component Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Diones,” Ultrasonics Sonochemistry 17, no. 1 (2010): 159–61.
   PubMed Web of Science ®Google Scholar
• R. Ghorbani-Vaghei, S. Noori, Z. Toghraei-Semiromi, and Z. Salimi, “One-Pot Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives under Solvent-Free Conditions,” RSC Advances 4, no. 89 (2014): 47925–8.
   Web of Science ®Google Scholar
• S.-H. Song, J. Zhong, Y.-H. He, and Z. Guan, “One-Pot Four-Component Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives,” Tetrahedron Letters 53, no. 52 (2012): 7075–7.
   Web of Science ®Google Scholar
• B. Maleki, S. Barat Nam Chalaki, S. Sedigh Ashrafi, E. Rezaee Seresht, F. Moeinpour, A. Khojastehnezhad, and R. Tayebee, “Caesium Carbonate Supported on Hydroxyapatite-Encapsulated Ni 0.5 Zn 0.5 Fe 2 O 4 Nanocrystallites as a Novel Magnetically Basic Catalyst for the One-Pot Synthesis of Pyrazolo[1,2-b]Phthalazine-5,10-Diones,” Applied Organometallic Chemistry 29, no. 5 (2015): 290–5.
   Web of Science ®Google Scholar
• G. Karthikeyan and A. Pandurangan, “Post Synthesis Alumination of KIT-6 Materials with Ia3d Symmetry and Their Catalytic Efficiency towards Multicomponent Synthesis of 1H-Pyrazolo[1,2-]Phthalazine-5,10-Dione Carbonitriles and Carboxylates,” Journal of Molecular Catalysis A: Chemical 361–362 (2012): 58–67.
   Google Scholar
• J. Safaei-Ghomi, H. Shahbazi-Alavi, A. Ziarati, R. Teymuri, and M. R. Saberi, “A Highly Flexible Green Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives with CuI Nanoparticles as Catalyst under Solvent-Free Conditions,” Chinese Chemical Letters 25, no. 3 (2014): 401–5.
   Web of Science ®Google Scholar
• M. Kidwai and R. Chauhan, “A Rapid and an Efficient Route to the One-Pot, Multicomponent Synthesis of 1 H -Pyrazolo[1,2-b] Phthalazine-5,10-Dione Ring Systems,” Journal of Heterocyclic Chemistry 51, no. 6 (2014): 1689–96.
   Web of Science ®Google Scholar
• A. G. Mulik, D. R. Chandam, D. R. Patil, P. P. Patil, G. N. Mulik, S. T. Salunkhe, and M. B. Deshmukh, “Protic Ionic Liquids: A Lucid, Rational Tool for Synthesis of Phthalazinediones, Quinoxalines and Benzopyrans,” Research on Chemical Intermediates 41, no. 12 (2015): 10085–96.
   Web of Science ®Google Scholar
• A. Patil, T. Lohar, A. Mane, S. Kamat, and R. Salunkhe, “Deep Eutectic Solvent an Efficient Reaction Medium for the Synthesis of Chromeno Pyrazolo and Indazolo Phthalazine Derivatives,” Journal of Heterocyclic Chemistry 56, no. 11 (2019): 3145–51.
   Web of Science ®Google Scholar
• A. Vafaee, A. Davoodnia, M. Pordel, and M. R. Bozorgmehr, “An Efficient and High-Yielding One-Pot Synthesis of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Diones Catalyzed by Sodium Hydrogen Carbonate under Solvent-Free Conditions,” Oriental Journal of Chemistry 31, no. 4 (2015): 2153–8.
   Web of Science ®Google Scholar
• H. R. Shaterian and M. Mohammadnia, “Mild Preparation of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives with Magnetic Fe3O4 Nanoparticles Coated by (3-Aminopropyl)-Triethoxysilane as Catalyst under Ambient and Solvent-Free Conditions,” Research on Chemical Intermediates 40, no. 1 (2014): 371–83.
   Web of Science ®Google Scholar
• V. S. Dofe, A. P. Sarkate, Z. M. Shaikh, C. K. Jadhav, A. S. Nipte, and C. H. Gill, “Ultrasound-Assisted Synthesis of Novel Pyrazole and Pyrimidine Derivatives as Antimicrobial Agents,” Journal of Heterocyclic Chemistry 55, no. 3 (2018): 756–62.
   Web of Science ®Google Scholar
• C. K. Jadhav, A. S. Nipate, A. V. Chate, V. S. Dofe, J. N. Sangshetti, V. M. Khedkar, and C. H. Gill, “Rapid Construction of Substituted Dihydrothiophene Ureidoformamides at Room Temperature Using Diisopropyl Ethyl Ammonium Acetate: A Green Perspective,” ACS Omega 5, no. 45 (2020): 29055–67.
   PubMed Web of Science ®Google Scholar
• Q. Zhang, S. Zhang, and Y. Deng, “Recent Advances in Ionic Liquid Catalysis,” Green Chemistry 13, no. 10 (2011): 2619.
   Web of Science ®Google Scholar
• P. A. Hunt, C. R. Ashworth, and R. P. Matthews, “Hydrogen Bonding in Ionic Liquids,” Chemical Society Reviews 44, no. 5 (2015): 1257–88.
   PubMed Web of Science ®Google Scholar
• L. M. Ramos, M. O. Rodrigues, and B. A. D. Neto, “Mechanistic Knowledge and Noncovalent Interactions as the Key Features for Enantioselective Catalysed Multicomponent Reactions: A Critical Review,” Organic & Biomolecular Chemistry 17, no. 31 (2019): 7260–9.
   PubMed Web of Science ®Google Scholar
• C. K. Jadhav, A. S. Nipate, A. V. Chate, V. D. Songire, A. P. Patil, and C. H. Gill, “Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate,” ACS Omega 4, no. 27 (2019): 22313–24.
   PubMed Web of Science ®Google Scholar
• A. V. Chate, S. P. Kamdi, A. N. Bhagat, C. K. Jadhav, A. Nipte, A. P. Sarkate, S. V. Tiwari, and C. H. Gill, “Design, Synthesis and SAR Study of Novel Spiro [Pyrimido[5,4-b]Quinoline-10,5′-Pyrrolo[2,3-d]Pyrimidine] Derivatives as Promising Anticancer Agents,” Journal of Heterocyclic Chemistry 55, no. 10 (2018): 2297–302.
   Web of Science ®Google Scholar
• A. S. Nipate, C. K. Jadhav, A. V. Chate, K. S. Taur, and C. H. Gill, “β‐Cyclodextrin Catalyzed Access to Fused 1,8‐Dihydroimidazo[2,3‐b] Indoles via One‐Pot Multicomponent Cascade in Aqueous Ethanol: Supramolecular Approach toward Sustainability,” Journal of Heterocyclic Chemistry 57, no. 2 (2020): 820–9.
   Web of Science ®Google Scholar
• A. V. Chate, A. S. Kulkarni, C. K. Jadhav, A. S. Nipte, and G. M. Bondle, “Multicomponent Reactions and Supramolecular Catalyst: A Perfect Synergy for Eco‐Compatible Synthesis of Pyrido[2,3‐ d] Pyrimidines in Water,” Journal of Heterocyclic Chemistry 57, no. 5 (2020): 2184–93.
   Web of Science ®Google Scholar
• C. K. Jadhav, A. S. Nipate, A. V. Chate, A. P. Patil, and C. H. Gill, “Ionic Liquid Catalyzed One‐Pot Multi‐Component Synthesis of Fused Pyridine Derivatives: A Strategy for Green and Sustainable Chemistry,” Journal of Heterocyclic Chemistry 57, no. 12 (2020): 4291–303.
   Web of Science ®Google Scholar
• C. K. Jadhav, A. S. Nipate, A. V. Chate, P. M. Kamble, G. A. Kadam, V. S. Dofe, V. M. Khedkar, and C. H. Gill, “Room Temperature Ionic Liquid Promoted Improved and Rapid Synthesis of Highly Functionalized Imidazole and Evaluation of Their Inhibitory Activity against Human Cancer Cells,” Journal of the Chinese Chemical Society 68, no. 6 (2021): 1067–1081.
   Web of Science ®Google Scholar