Diversity Oriented Synthesis of Oxygen-Heterocycles, Warfarin Analogs Utilizing Microwave-Assisted Dimethyl Urea-Based Deep Eutectic Solvents

References and notes

• Q. Zhang, K.D.O. Vigier, S. Royer, and F. Jérôme, “Deep Eutectic Solvents: Syntheses, Properties and Applications,”Chemical Society Reviews 41, no. 21 (2012): 7108–46.
   PubMed Web of Science ®Google Scholar
• V. Krishnakumar, N.G. Vindhya, B.K. Mandal, and F.-R. Nawaz Khan, “Green Chemical Approach: Low-Melting Mixture as a Green Solvent for Efficient Michael Addition of Homophthalimides with Chalcones,”Industrial & Engineering Chemistry Research 53, no. 26 (2014): 10814–9.
   Web of Science ®Google Scholar
• C. Teja, and F.R. Nawaz Khan, “Choline Chloride-Based Deep Eutectic Systems in Sequential FriedläNder Reaction and Palladium-Catalyzed sp3 CH Functionalization of Methyl Ketones,” ACS Omega 4, no. 5 (2019): 8046–55.
   PubMed Web of Science ®Google Scholar
• S. Prameela, and F.R. Nawaz Khan, “Ru-Catalyzed Sequential Dehydrogenative Friedlander Reaction/sp3 C–H Activation/Knovenagel Condensation in the Regioselective Synthesis of Chimanine B Analogues,”European Journal of Organic Chemistry 2020, no. 19 (2020): 2888–903.
   Web of Science ®Google Scholar
• S. Prameela, and F.R. Nawaz Khan, “Ir (I)‐Catalyzed Synthesis of (E)‐4‐Benzylidenylacridines and (E)‐2‐Styrylquinoline‐3‐Carboxamide through Sequential Suzuki–Miyaura Coupling, Dehydrogenative Friedländer Reaction, and sp3‐C–H Activation,”European Journal of Organic Chemistry 2020, no. 33 (2020): 5394–410.
   Web of Science ®Google Scholar
• A.P. Abbott, D. Boothby, G. Capper, D.L. Davies, and R.K. Rasheed, “Deep Eutectic Solvents Formed between Choline Chloride and Carboxylic Acids: versatile Alternatives to Ionic Liquids,”Journal of the American Chemical Society 126, no. 29 (2004): 9142–7.
   PubMed Web of Science ®Google Scholar
• E.L. Smith, A.P. Abbott, and K.S. Ryder, “Deep Eutectic Solvents (DESs) and Their Applications,”Chemical Reviews 114, no. 21 (2014): 11060–82.
   PubMed Web of Science ®Google Scholar
• G. Imperato, S. Höger, D. Lenoir, and B. König, “Low Melting Sugar–Urea–Salt Mixtures as Solvents for Organic Reactions—Estimation of Polarity and Use in Catalysis,”Green Chemistry 8, no. 12 (2006): 1051–5.
   Web of Science ®Google Scholar
• G. Imperato, E. Eibler, J. Niedermaier, and B. König, “Low-Melting Sugar–Urea–Salt Mixtures as Solvents for Diels–Alder Reactions,” Chemical Communications. 9, no. 9 (2005): 1170–2.
   Google Scholar
• C. Ruß, and B. König, “Low Melting Mixtures in Organic Synthesis–an Alternative to Ionic Liquids?,”Green Chemistry 14, no. 11 (2012): 2969–82.
   Web of Science ®Google Scholar
• J. Wang, H. Li, L. Zu, and W. Wang, “Highly Enantioselective Organocatalytic Michael Addition Reactions of Ketones with Chalcones,”Advanced Synthesis & Catalysis 348, no. 4–5 (2006): 425–8.
   Web of Science ®Google Scholar
• W. Yang, and D.-M. Du, “Highly Enantioselective Michael Addition of Nitroalkanes to Chalcones Using Chiral Squaramides as Hydrogen Bonding Organocatalysts,”Organic Letters 12, no. 23 (2010): 5450–3.
   PubMed Web of Science ®Google Scholar
• D.Y. Kim, S.C. Huh, and S.M. Kim, “Enantioselective Michael Reaction of Malonates and Chalcones by Phase-Transfer Catalysis Using Chiral Quaternary Ammonium Salt,”Tetrahedron Letters. 42, no. 36 (2001): 6299–301.
   Web of Science ®Google Scholar
• G.S. Hassan, H.H. Georgey, R.F. George, and E.R. Mohamed, “Aurones and Furoaurones: Biological Activities and Synthesis,”Bull. Fac. Pharm. Cairo Univ 56, no. 2 (2018): 121–7.
   Google Scholar
• M.I. Ahmad, S. Dixit, R. Konwar, P.G. Vasdev, A.K. Yadav, S. Tripathi, M.M. Gupta, A. Sharma, and A. Gupta, “Syntheses of Conformationally Restricted Benzopyran Based Triarylethylenes as Growth Inhibitors of Carcinoma Cells,”Bioorganic & Medicinal Chemistry Letters 27, no. 22 (2017): 5040–5.
   PubMed Web of Science ®Google Scholar
• Y.-Q. Hu, Z. Xu, S. Zhang, X. Wu, J.-W. Ding, Z.-S. Lv, and L.-S. Feng, “Recent Developments of Coumarin-Containing Derivatives and Their anti-Tubercular Activity,”European Journal of Medicinal Chemistry 136, (2017): 122–30.
   PubMed Web of Science ®Google Scholar
• C.-R. Su, S.F. Yeh, C.M. Liu, A.G. Damu, T.-H. Kuo, P.-C. Chiang, K.F. Bastow, K.-H. Lee, and T.-S. Wu, “Anti-HBV and Cytotoxic Activities of Pyranocoumarin Derivatives,”Bioorganic & Medicinal Chemistry 17, no. 16 (2009): 6137–43.
   PubMed Web of Science ®Google Scholar
• U. Kusampally, R. Pagadala, and C.R. Kamatala, “Metal Free Lewis Acid Promoted One-Pot Synthesis of 14-Aryl-14H Dibenzo [a, j] Xanthenes and Their Simple Biological Evolution,”Tetrahedron Letters. 58, no. 33 (2017): 3316–8.
   Web of Science ®Google Scholar
• M.S.L. Kumar, et al. “Diversity Oriented Synthesis of Chromene-Xanthene Hybrids as anti-Breast Cancer Agents,” Bioorganic and Medicinal Chemistry Letters. 28, (2018): 778–82.
   PubMed Web of Science ®Google Scholar
• Y. Zhang, H. Zhong, T. Wang, D. Geng, M. Zhang, and K. Li, “Synthesis of Novel 2, 5-Dihydrofuran Derivatives and Evaluation of Their Anticancer Activity,”European Journal of Medicinal Chemistry 48, (2012): 69–80.
   PubMed Web of Science ®Google Scholar
• K. Sugimoto, K. Tamura, C. Tohda, N. Toyooka, H. Nemoto, and Y. Matsuya, “ Structure-activity-relationship Studies on Dihydrofuran-Fused Perhydrophenanthrenes as an Anti-Alzheimer's Disease Agent,”Bioorganic & Medicinal Chemistry 21, no. 15 (2013): 4459–71.
   PubMed Web of Science ®Google Scholar
• P. Laurin, D. Ferroud, M. Klich, C. Dupuis-Hamelin, P. Mauvais, P. Lassaigne, A. Bonnefoy, and B. Musicki, “Synthesis and in Vitro Evaluation of Novel Highly Potent Coumarin Inhibitors of Gyrase B,”Bioorganic & Medicinal Chemistry Letters 9, no. 14 (1999): 2079–84.
   PubMed Web of Science ®Google Scholar
• R.H. Vekariya, and H.D. Patel, “Recent Advances in the Synthesis of Coumarin Derivatives via Knoevenagel Condensation: A Review,” Synthetic Communications. 44, no. 19 (2014): 2756–88.
   Web of Science ®Google Scholar
• Hamdi, N., Saoud, M. & Romerosa, A. Bioactive Heterocycles V (Berlin: Springer, 2007), 283–301.
   Google Scholar
• Y. Liu, J. Zhu, J. Qian, B. Jiang, and Z. Xu, “ Gold(III)-catalyzed tandem conjugate addition/annulation of 4-hydroxycoumarins with α,β-unsaturated ketones ,”The Journal of Organic Chemistry 76, no. 21 (2011): 9096–101.
   PubMed Web of Science ®Google Scholar
• M. Gohain, J.H. van Tonder, and B.C. Bezuidenhoudt, “Bi (OTf) 3-Catalyzed Solvent-Free Synthesis of Pyrano [3, 2-c] Coumarins through a Tandem Addition/Annulation Reaction between Chalcones and 4-Hydroxycoumarins,” Tetrahedron Letters 54, no. 29 (2013): 3773–6.
   Web of Science ®Google Scholar
• A.K. Bagdi, A. Majee, and A. Hajra, “Regioselective Synthesis of Pyrano [3, 2-c] Coumarins via Cu (II)-Catalyzed Tandem Reaction,”Tetrahedron Letters. 54, no. 29 (2013): 3892–5.
   Web of Science ®Google Scholar
• S. Yaragorla, P.L. Saini, and G. Singh, “Alkaline Earth Metal Catalyzed Cascade, One-Pot, Solvent-Free, and Scalable Synthesis of Pyranocoumarins and Benzo [b] Pyrans,”Tetrahedron Letters. 56, no. 13 (2015): 1649–53.
   Web of Science ®Google Scholar
• S.U. Pandya, U.R. Pandya, B.R. Hirani, and D.I. Brahmbhatt, “One Pot Synthesis of Diarylpyrido [3, 2‐c] Coumarins,”Journal of Heterocyclic Chemistry 43, no. 3 (2006): 795–8.
   Web of Science ®Google Scholar
• G.H. Mahdavinia, and S. Peikarporsan, “Cyclization of α, α′-Bis (Substituted-Benzylidene) Cyclohexanones and 4-Hydroxycoumarin: synthesis of 11-Benzylidene-8, 9, 10, 11-Tetrahydro-7-Phenyl-6H, 7H-Chromeno [4, 3-b] Chromen-6-Ones as New Pyranochromene Derivatives,”Monatshefte Für Chemie - Chemical Monthly 144, no. 3 (2013): 415–9.
   Google Scholar
• N. Ahmed, and B.V. Babu, “Efficient Route to Highly Functionalized Chalcone-Based Pyranocoumarins via Iodine-Promoted Michael Addition Followed by Cyclization of 4-Hydroxycoumarins,” Synthetic Communications. 43, no. 22 (2013): 3044–53.
   Web of Science ®Google Scholar
• S. Mahato, S. Santra, R. Chatterjee, G.V. Zyryanov, A. Hajra, and A. Majee, “Brønsted Acidic Ionic Liquid-Catalyzed Tandem Reaction: An Efficient Approach towards Regioselective Synthesis of Pyrano [3, 2-c] Coumarins under Solvent-Free Conditions Bearing Lower E-Factors,”Green Chemistry 19, no. 14 (2017): 3282–95.
   Web of Science ®Google Scholar
• S. Khodabakhshi, “Green Synthesis of Naphthyloyl Biscoumarins, Naphthyloyl Pyranocoumarins, and Naphthyloyl Amidocoumarins Based on Naphthyl Glyoxals Catalyzed by ZnO Nanowires,”Polycyclic Aromatic Compounds. 34, no. 5 (2014): 573–87.
   Web of Science ®Google Scholar
• Z. Karimi-Jaberi, B. Masoudi, A. Rahmani, and K. Alborzi, “Triethylammonium Hydrogen Sulfate [Et3NH][HSO4] as an Efficient Ionic Liquid Catalyst for the Synthesis of Coumarin Derivatives,”Polycyclic Aromatic Compounds. 40, no. 1 (2020): 99–107.
   Web of Science ®Google Scholar
• X.Y. Hu, X.S. Fan, X.Y. Zhang, G.R. Qu, and Y.Z. Li, “Solvent-Free Synthesis of 5-Oxo-5, 6, 7, 8-Tetrahydro-4 H-Benzo-[b]-Pyran Derivatives under Microwave Irradiation,”Canadian Journal of Chemistry 84, no. 8 (2006): 1054–7.
   Web of Science ®Google Scholar
• Q. Li, X. Hu, W. Li, F. Yang, X. Yang, L. Sun, L. Zhou, J. Qi, and Y. Yu, “Preparation of 5-Oxo-5, 6, 7, 8-Tetrahydro-4H-Benzo-[b]-Pyran Derivatives in Ionic Liquids,”Journal of Chemical Research 2008, no. 6 (2008): 331–3.
   Google Scholar
• Z.W. Chen, Y.L. Wang, R.E. Chen, and W.K. Su, “Ytterbium Triflate Hydrate Catalyzed Michael Addition and Cyclocondensation of α, β-Unsaturated Ketones with Active Methylene Compounds,” Chinese Chemical Letters 19, no. 9 (2008): 1024–6.
   Web of Science ®Google Scholar
• S. Samanta, A.D. Gupta, R. Mondal, and A.K. Mallik, “A Simple Synthesis of E-9-Aryl-5-Arylidene-1-Oxo-1, 2, 3, 4, 5, 6, 7, 8-Octahydroxanthenes and Their Lower Analogues from E, E-α, α′-Diarylidenecycloalkanones,”Journal of Chemical Sciences 125, no. 4 (2013): 737–43.
   Web of Science ®Google Scholar
• Z. Karimi-Jaberi, and B. Pooladian, “Efficient One-Pot Synthesis of Some New Xanthene Derivatives Based on the Reaction of Dimedone with α, α′-Bis (Substituted-Benzylidene) Cycloalkanones Using Catalytic Amount of pTSA,” Synthetic Communications. 43, no. 8 (2013): 1188–99.
   Web of Science ®Google Scholar
• V. Polshettiwar, and R.S. Varma, “Microwave-Assisted Organic Synthesis and Transformations Using Benign Reaction Media,”Accounts of Chemical Research 41, no. 5 (2008): 629–39.
   PubMed Web of Science ®Google Scholar
• B.A. Roberts, and C.R. Strauss, “Toward rapid, "green", predictable microwave-assisted synthesis,”Accounts of Chemical Research 38, no. 8 (2005): 653–61.
   PubMed Web of Science ®Google Scholar
• A. Stadler, S. Pichler, G. Horeis, and C.O. Kappe, “Microwave-Enhanced Reactions under Open and Closed Vessel Conditions. A Case Study,”Tetrahedron 58, no. 16 (2002): 3177–83.
   Web of Science ®Google Scholar
• C.O. Kappe, “How to Measure Reaction Temperature in Microwave-Heated Transformations,”Chemical Society Reviews 42, no. 12 (2013): 4977–90.
   PubMed Web of Science ®Google Scholar
• A. de la Hoz, A. Diaz-Ortiz, and A. Moreno, “Microwaves in Organic Synthesis. Thermal and Non-Thermal Microwave Effects,”Chemical Society Reviews 34, no. 2 (2005): 164–78.
   PubMed Web of Science ®Google Scholar
• S.M. Ghouse, Y.S. Kumar, J.S. Jin, J.-P. Kim, J.S. Bae, E.H. Chung, et al. “Green Chemical Approach: microwave Assisted, Titanium Dioxide Nanoparticles Catalyzed, Convenient and Efficient C–C Bond Formation in the Synthesis of Highly Functionalized Quinolines and Quinolinones,”RSC Advances. 4, no. 84 (2014): 44408–17.
   Web of Science ®Google Scholar
• S. Maiti, P.T. Perumal, and J.C. Menéndez, “CAN-Promoted, Diastereoselective Synthesis of Fused 2, 3-Dihydrofurans and Their Transformation into Tetrahydroindoles,”Tetrahedron 66, no. 49 (2010): 9512–8.
   Web of Science ®Google Scholar