Ionic Liquid [(EMIM)Ac] Catalyzed Green and Efficient Synthesis of Pyrano[2,3-c]Pyrazole Derivatives

Reference

• Bekington Myrboh, Hormi Mecadon, Md Rumum Rohman, Mantu Rajbangshi, Icydora Kharkongor, Badaker M. Laloo, Iadeishisha Kharbangar, and Baskhemlang Kshiar, “Synthetic Developments in Functionalized Pyrano [2, 3-c] Pyrazoles. A Review,” Organic Preparations and Procedures International 45, no. 4 (2013): 253–303. doi:10.1080/00304948.2013.798566.
   Web of Science ®Google Scholar
• Ahmed Fadda, Ahmed El-Mekabaty, and Khaled M. Elattar, “Chemistry of Enaminonitriles of Pyrano [2, 3-c] Pyrazole and Related Compounds,” Synthetic Communications 43, no. 20 (2013): 2685–719. doi:10.1080/00397911.2012.744842.
   Web of Science ®Google Scholar
• Manouchehr Mamaghani, and Roghayeh Hossein Nia, “A Review on the Recent Multicomponent Synthesis of Pyranopyrazoles,” Polycyclic Aromatic Compounds 41, no. 2 (2021): 223–91. doi:10.1080/10406638.2019.1584576.
   Web of Science ®Google Scholar
• R. Stolle, “Ueber Die Condensation Von Acetessigester Mit Phenyl‐Methyl‐Pyrazolon Und Die Einwirkungsproducte Von Phenylhydrazin Und Hydrazin Auf Dehydracetsäure,” Berichte der deutschen chemischen Gesellschaft 38, no. 3 (1905): 3023–32.
   Google Scholar
• Hans Junek, and Hans Aigner, “Synthesen Mit Nitrilen, XXXV. Reaktionen Von Tetracyanäthylen Mit Heterocyclen,” Chemische Berichte 106, no. 3 (1973): 914–21. doi:10.1002/cber.19731060323.
   Google Scholar
• H. H. Otto, “Synthesis of Some 4H-pyrano (2.3-c) Pyrazoles,” Archiv der Pharmazie 307, no. 6 (1974): 444–7. doi:10.1002/ardp.19743070609.
   PubMed Web of Science ®Google Scholar
• Nadia Mohamed, Nahed Khaireldin, A. Fahmyb, and A. El-Sayeda, “Facile Synthesis of Fused Nitrogen Containing Heterocycles as Anticancer Agents,” Der Pharma Chemica 2, no. 1 (2010): 400–17.
   Google Scholar
• Hadi Adibi, Leila Hosseinzadeh, Sepideh Farhadi, and Farahnaz Ahmadi, “Synthesis and Cytotoxic Evaluation of 6-Amino-4-Aryl-3-Methyl-2, 4-Dihydropyrano [2, 3-C] Pyrazole-Carbonitrile Derivatives Using Borax with Potential Anticancer Effects,” Journal of Reports in Pharmaceutical Sciences 2, no. 2 (2013): 27–35.
   Google Scholar
• Rahul Ramtekkar, Kandhasamy Kumarvel, Gnanasambandam Vasuki, K. Sekar, and R. Krishna, “Computer-Aided Drug Design of Pyranopyrazoles and Related Compounds for Checkpoint Kinase-1,” Letters in Drug Design & Discovery 6, no. 8 (2009): 579–84. doi:10.2174/157018009789353455.
   Web of Science ®Google Scholar
• Nicolas Foloppe, Lisa M. Fisher, Rob Howes, Andrew Potter, Alan G. S. Robertson, and Allan E. Surgenor, “Identification of Chemically Diverse Chk1 Inhibitors by Receptor-Based Virtual Screening,” Bioorganic & Medicinal Chemistry 14, no. 14 (2006): 4792–802. doi:10.1016/j.bmc.2006.03.021.
   PubMed Web of Science ®Google Scholar
• Magda M. F. Ismail, Nagy M. Khalifa, Hoda H. Fahmy, Eman S. Nossier, and Mohamed M. Abdulla, “Design, Docking, and Synthesis of Some New Pyrazoline and Pyranopyrazole Derivatives as anti‐Inflammatory Agents,” Journal of Heterocyclic Chemistry 51, no. 2 (2014): 450–8. doi:10.1002/jhet.1757.
   Web of Science ®Google Scholar
• Adel Hamed Mandour, Eslam Reda El-Sawy, Manal Shaaban Ebaid, and Seham M. Hassan, “sinteza i potencijalno biološko djelovanje novih 3-((N-supstituiranih indol-3-il) metilenamino)-6-amino-4-aril-pirano (2, 3-c) pirazol-5-karbonitrila i 3, 6-diamino-4-(N-supstituiranih indol-3-il) pirano (2, 3-c) pirazol-5-karbonitrila,” Acta Pharmaceutica (Zagreb, Croatia) 62, no. 1 (2012): 15–30. doi:10.2478/v10007-012-0007-0.
   PubMed Web of Science ®Google Scholar
• Taisei Ueda, Hideshi Mase, Noriichi Oda, and Isoo Ito, “Synthesis of Pyrazolone Derivatives. XXXIX. Synthesis and Analgesic Activity of Pyrano[2,3-c]Pyrazoles,” Chemical & Pharmaceutical Bulletin 29, no. 12 (1981): 3522–8. doi:10.1248/cpb.29.3522.
   PubMed Web of Science ®Google Scholar
• Anand Saundane, Prabhaker Walmik, Manjunatha Yarlakatti, Vijaykumar Katkar, and Vaijinath A. Verma, “Synthesis and Biological Activities of Some New Annulated Pyrazolopyranopyrimidines and Their Derivatives Containing Indole Nucleus,” Journal of Heterocyclic Chemistry 51, no. 2 (2014): 303–14. doi:10.1002/jhet.1582.
   Web of Science ®Google Scholar
• D. Capodanno, J. L. Ferreiro, and D. J. Angiolillo, “Antiplatelet Therapy: new Pharmacological Agents and Changing Paradigms,” Journal of Thrombosis and Haemostasis 11 (2013): 316–29. doi:10.1111/jth.12219.
   PubMed Web of Science ®Google Scholar
• G. Tacconi, G. Gatti, G. Desimoni, and V. Messori, “A New Route to 4H‐Pyrano [2, 3‐c] Pyrazoles,” Journal für Praktische Chemie 322, no. 5 (1980): 831–4. doi:10.1002/prac.19803220519.
   Google Scholar
• Sheu-Meei Yu, Sheng-Chu Kuo, Li-Jiau Huang, Selma Siu-Man Sun, Tur-Fu Huang, and Che-Ming Teng, “ Vasorelaxation of Rat Thoracic Aorta Caused by Two Ca(2+)-Channel Blockers, HA-22 and HA-23,” The Journal of Pharmacy and Pharmacology 44, no. 8 (1992): 667–71. doi:10.1111/j.2042-7158.1992.tb05491.x.
   PubMed Web of Science ®Google Scholar
• Fathy M. Abdelrazek, Peter. Metz, Nadia H. Metwally, and Sherif F. El‐Mahrouky, “Synthesis and Molluscicidal Activity of New Cinnoline and Pyrano [2, 3‐c] Pyrazole Derivatives,” Archiv der Pharmazie 339, no. 8 (2006): 456–60. doi:10.1002/ardp.200600057.
   PubMed Web of Science ®Google Scholar
• Debasis Das, Reena Banerjee, and Atanu Mitra, “Bioactive and Pharmacologically Important Pyrano [2, 3-c] Pyrazoles,” Journal of Chemical and Pharmaceutical Research 6, no. 11 (2014): 108–16.
   Google Scholar
• Dileep Kumar Yadav, and M. A. Quraishi, “Electrochemical Investigation of Substituted Pyranopyrazoles Adsorption on Mild Steel in Acid Solution,” Industrial & Engineering Chemistry Research 51, no. 24 (2012): 8194–210. doi:10.1021/ie3002155.
   Web of Science ®Google Scholar
• Răzvan C. Cioc, Eelco Ruijter, and Romano V. A. Orru, “Multicomponent Reactions: advanced Tools for Sustainable Organic Synthesis,” Green Chemistry 16, no. 6 (2014): 2958–75. doi:10.1039/C4GC00013G.
   Web of Science ®Google Scholar
• Ashishkumar Katariya, Devidas Bhagat, Maya Katariya, and Rajendra Pawar, “Green Techniques in Organic Synthesis and Its Advantages,” Journal of Medicinal Chemistry and Drug Design 3, no. 3 (2017): 62–6.
   Google Scholar
• Benjamin H. Rotstein, Serge Zaretsky, Vishal Rai, and Andrei K. Yudin, “Small Heterocycles in Multicomponent Reactions,” Chemical Reviews 114, no. 16 (2014): 8323–59. doi:10.1021/cr400615v.
   PubMed Web of Science ®Google Scholar
• V. K. Ahluwalia, and Mazaahir Kidwai, New Trends in Green Chemistry (Boston: Springer Science & Business Media, 2004).
   Google Scholar
• Mohammad Ali Zolfigol, Mahsa Tavasoli, Ahmad Reza Moosavi-Zare, Parvin Moosavi, Hendrik Gerhardus Kruger, Morteza Shiri, and Vahid Khakyzadeh, “Synthesis of Pyranopyrazoles Using Isonicotinic Acid as a Dual and Biological Organocatalyst,” RSC Advances 3, no. 48 (2013): 25681–5. doi:10.1039/c3ra45289a.
   Web of Science ®Google Scholar
• Madhusudana Reddy, V. P. Jayashankara, and M. A. Pasha, “Glycine-Catalyzed Efficient Synthesis of Pyranopyrazoles via One-Pot Multicomponent Reaction,” Synthetic Communications 40, no. 19 (2010): 2930–4. doi:10.1080/00397910903340686.
   Web of Science ®Google Scholar
• Hemant V. Chavan, Santosh B. Babar, Rahul U. Hoval, and Babasaheb P. Bandgar, “Rapid One-Pot, Four Component Synthesis of Pyranopyrazoles Using Heteropolyacid under Solvent-Free Condition,” Bulletin of the Korean Chemical Society 32, no. 11 (2011): 3963–6. doi:10.5012/bkcs.2011.32.11.3963.
   Web of Science ®Google Scholar
• Guda Mallikarjuna Reddy, and Jarem Raul Garcia, “Synthesis of Pyranopyrazoles under Eco‐Friendly Approach by Using Acid Catalysis,” Journal of Heterocyclic Chemistry 54, no. 1 (2017): 89–94. doi:10.1002/jhet.2544.
   Web of Science ®Google Scholar
• Aisha Siddekha, Aatika Nizam, and M. A. Pasha, “An Efficient and Simple Approach for the Synthesis of Pyranopyrazoles Using Imidazole (Catalytic) in Aqueous Medium, and the Vibrational Spectroscopic Studies on 6-Amino-4-(4'-Methoxyphenyl)-5-Cyano-3-Methyl-1-Phenyl-1,4-Dihydropyrano[2,3-c]Pyrazole Using Density Functional Theory, ” Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy 81, no. 1 (2011): 431–40. doi:10.1016/j.saa.2011.06.033.
   PubMed Web of Science ®Google Scholar
• Kuppusamy Kanagaraj, and Kasi Pitchumani, “Solvent-Free Multicomponent Synthesis of Pyranopyrazoles: Per-6-Amino-β-Cyclodextrin as a Remarkable Catalyst and Host,” Tetrahedron Letters 51, no. 25 (2010): 3312–6. doi:10.1016/j.tetlet.2010.04.087.
   Web of Science ®Google Scholar
• Sunil N. Darandale, Jaiprakash N. Sangshetti, and Devanand B. Shinde, “Ultrasound Mediated, Sodium Bisulfite Catalyzed, Solvent Free Synthesis of 6-Amino-3-Methyl-4-Substitued-2, 4-Dihydropyrano [2, 3-c] Pyrazole-5-Carbonitrile,” Journal of the Korean Chemical Society 56, no. 3 (2012): 328–33. doi:10.5012/jkcs.2012.56.3.328.
   Google Scholar
• Ashishkumar Katariya, Satish Deshmukh, S. B. Munde, Maya Katariya, and Rajendra Pawar,"Green and expeditious one pot synthesis of pyrano[2,3-c]pyrazole using potassium ter-butoxide catalyst in aqueous medium" International Journal of Green and Herbal Chemistry 8, no. 3 (2019): 790–7.
   Google Scholar
• Hormi Mecadon, Md Rumum Rohman, Mantu Rajbangshi, and Bekington Myrboh, “γ-Alumina as a Recyclable Catalyst for the Four-Component Synthesis of 6-Amino-4-Alkyl/Aryl-3-Methyl-2, 4-Dihydropyrano [2, 3-c] Pyrazole-5-Carbonitriles in Aqueous Medium,” Tetrahedron Letters 52, no. 19 (2011): 2523–5. doi:10.1016/j.tetlet.2011.03.036.
   Web of Science ®Google Scholar
• Jitender M. Khurana, Bhaskara Nand, and Sanjay Kumar, “Rapid Synthesis of Polyfunctionalized Pyrano [2, 3-c] Pyrazoles via Multicomponent Condensation in Room-Temperature Ionic Liquids,” Synthetic Communications 41, no. 3 (2011): 405–10. doi:10.1080/00397910903576669.
   Web of Science ®Google Scholar
• Farid Moeinpour, and Amir Khojastehnezhad, “Polyphosphoric Acid Supported on Ni0. 5Zn0. 5Fe2O4 Nanoparticles as a Magnetically-Recoverable Green Catalyst for the Synthesis of Pyranopyrazoles,” Arabian Journal of Chemistry 10 (2017): S3468–S3474. doi:10.1016/j.arabjc.2014.02.009.
   Web of Science ®Google Scholar
• Maryam Babaie, and Hassan Sheibani, “Nanosized Magnesium Oxide as a Highly Effective Heterogeneous Base Catalyst for the Rapid Synthesis of Pyranopyrazoles via a Tandem Four-Component Reaction,” Arabian Journal of Chemistry 4, no. 2 (2011): 159–62. doi:10.1016/j.arabjc.2010.06.032.
   Web of Science ®Google Scholar
• Arijit Saha, Soumen Payra, and Subhash Banerjee, “One-Pot Multicomponent Synthesis of Highly Functionalized Bio-Active Pyrano [2, 3-c] Pyrazole and Benzylpyrazolyl Coumarin Derivatives Using ZrO2 Nanoparticles as a Reusable Catalyst,” Green Chemistry 17, no. 5 (2015): 2859–66. doi:10.1039/C4GC02420F.
   Web of Science ®Google Scholar
• Ashok Vishram Borhade, and Bhagwat Karbhari Uphade, “ZnS Nanoparticles as an Efficient and Reusable Catalyst for Synthesis of 4H-Pyrano [2, 3-c] Pyrazoles,” Journal of the Iranian Chemical Society 12, no. 6 (2015): 1107–13. doi:10.1007/s13738-014-0571-y.
   Web of Science ®Google Scholar
• Gnanasambandam Vasuki, and Kandhasamy Kumaravel, “Rapid Four-Component Reactions in Water: synthesis of Pyranopyrazoles,” Tetrahedron Letters 49, no. 39 (2008): 5636–8. doi:10.1016/j.tetlet.2008.07.055.
   Web of Science ®Google Scholar
• Javad Ebrahimi, Ali Mohammadi, Vahid Pakjoo, Ehsan Bahramzade, and Amir Habibi, “Highly Efficient Solvent-Free Synthesis of Pyranopyrazoles by a Brønsted-Acidic Ionic Liquid as a Green and Reusable Catalyst,” Journal of Chemical Sciences 124, no. 5 (2012): 1013–7. doi:10.1007/s12039-012-0310-9.
   Web of Science ®Google Scholar
• Siddique A. Ansari, Satish U. Deshmukh, Rajesh B. Patil, Manoj G. Damale, Rajendra H. Patil, Hamad M. Alkahtani, Abdulrahman A. Almehizia, Hanaa M. Al‐Tuwajiri, Fadilah S. Aleanizy, Fulwah Y. Alqahtani, et al, “Identification of Promising Biofilm Inhibitory and Cytotoxic Quinazolin‐4‐One Derivatives: Synthesis, Evaluation, Molecular Docking and ADMET Studies,” ChemistrySelect 4, no. 12 (2019): 3559–66. doi:10.1002/slct.201803795.
   Web of Science ®Google Scholar
• Vinod V. Thorat, Satish A. Dake, Satish U. Deshmukh, Elayaraja Rasokkiyam, Farees Uddin, and Rajendra P. Pawar, “Ionic Liquid Mediated Synthesis of Novel Tetrahydroimidazo [1, 2-a] Pyrimidine-6-Carboxylate Derivatives,” Letters in Organic Chemistry 10, no. 3 (2013): 178–84. doi:10.2174/1570178611310030006.
   Web of Science ®Google Scholar
• Satish Uttamrao Deshmukh, Kiran Ramesh Kharat, Gajanan Gulabrao Kadam, and Rajendra Pundlikrao Pawar, “Synthesis of Quinazolinones Derivatives an Antiproliferative Agent against Human Lung Carcinoma Cells,” European Journal of Chemistry 8, no. 3 (2017): 317–20. doi:10.5155/eurjchem.8.3.317-320.1586.
   Google Scholar
• Bourbigou Hélene Olivier, L. Magna, and D. Morvan, “Ionic Liquids and Catalysis: Recent Progress from Knowledge to Applications,” Applied Catalysis A: General 373, no. 1-2 (2010): 1–56. doi:10.1016/j.apcata.2009.10.008.
   Web of Science ®Google Scholar
• Bakhtar Ullah, Jingwen Chen, Zhiguo Zhang, Huabin Xing, Qiwei Yang, Zongbi Bao, and Qilong Ren, “1-Ethyl-3-Methylimidazolium Acetate as a Highly Efficient Organocatalyst for Cyanosilylation of Carbonyl Compounds with Trimethylsilyl Cyanide,” Scientific Reports 7, no. 1 (2017): 42699–7. doi:10.1038/srep42699.
   PubMedGoogle Scholar
• Gerald Ebner, Philipp Vejdovszky, Ronny Wahlström, Anna Suurnäkki, Michael Schrems, Paul Kosma, Thomas Rosenau, and Antje Potthast, “The Effect of 1-Ethyl-3-Methylimidazolium Acetate on the Enzymatic Degradation of Cellulose,” Journal of Molecular Catalysis B: Enzymatic 99 (2014): 121–9. doi:10.1016/j.molcatb.2013.11.001.
   Web of Science ®Google Scholar