Mohammadi, M., Rezaei, A., Khazaei, A., Xuwei, S. & Huajun, Z. Targeted development of sustainable green catalysts for oxidation of alcohols via tungstate-decorated multifunctional amphiphilic carbon quantum dots. ACS Appl. Mater. Inter. 36, 33194–33206 (2019).ArticleÂ
Google ScholarÂ
Makone, S. S. & Niwadange, S. N. Green chemistry alternatives for sustainable development in organic synthesis. Green Chem. 3, 113–115 (2016).
Google ScholarÂ
Rahmati, M. & Habibi, D. Synthesis of a novel acidic ionic liquid catalyst and its application for preparation of pyridines via a cooperative vinylogous anomeric-based oxidation. Res. Chem. Intermed. 47, 1643–1661 (2021).ArticleÂ
CASÂ
Google ScholarÂ
Greer, A. J., Jacquemin, J. & Hardacre, C. Industrial applications of ionic liquids. Molecules 21, 5207 (2020).ArticleÂ
Google ScholarÂ
PÅ‚otka-Wasylka, J., De la Guardia, M., Andruch, V. & Vilková, M. Deep eutectic solvents vs ionic liquids: Similarities and differences. Microchem. J. 159, 105539 (2020).ArticleÂ
Google ScholarÂ
Abbott, A. P. et al. Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chainsElectronic supplementary information (ESI) available: Plot of conductivity vs. temperature for the ionic liquid formed from zinc chloride and choline chloride (2∶1). Chem. Commun. 19, 2010–2011 (2001).ArticleÂ
Google ScholarÂ
Abbott, A. P., Capper, G., Davies, D. L., Rasheed, R. K. & Tambyrajah, V. Novel solvent properties of choline chloride/urea mixtures. Chem. Commun. 1, 70–71 (2003).ArticleÂ
Google ScholarÂ
Abbott, A. P., Boothby, D., Capper, G., Davies, D. L. & Rasheed, R. K. Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids. J. Am. Chem. Soc. 126, 9142–9147 (2004).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Hayyan, M. et al. Are deep eutectic solvents benign or toxic?. Chemosphere 90, 2193–2195 (2013).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
Google ScholarÂ
Dai, Y., Van Spronsen, J., Witkamp, G. J., Verpoorte, R. & Choi, Y. H. Ionic liquids and deep eutectic solvents in natural products research: Mixtures of solids as extraction solvents. J. Nat. Prod. 76, 2162–2173 (2013).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
DomÃnguez de MarÃa, P. Recent trends in (ligno) cellulose dissolution using neoteric solvents: Switchable, distillable and bio-based ionic liquids. J. Chem. Technol. Biotechnol. 89, 11–18 (2014).ArticleÂ
Google ScholarÂ
Hansen, B. B. et al. Deep eutectic solvents: A review of fundamentals and applications. Chem. Rev. 3, 1232–1285 (2020).
Google ScholarÂ
Omar, K. A. & Sadeghi, R. Physicochemical properties of deep eutectic solvents: A review. J. Mol. Liq. 360, 119524 (2022).ArticleÂ
CASÂ
Google ScholarÂ
Ãœnlü, A. E., Arıkaya, A. & Takaç, S. Use of deep eutectic solvents as catalyst: A mini-review. Green Process Synth. 1, 355–372 (2019).ArticleÂ
Google ScholarÂ
Morais, E. S., Freire, M. G., Freire, C. S., Coutinho, J. A. & Silvestre, A. J. Enhanced conversion of xylan into furfural using acidic deep eutectic solvents with dual solvent and catalyst behavior. ChemSusChem 4, 784–790 (2020).ArticleÂ
Google ScholarÂ
Abranches, D. O. & Coutinho, J. A. Is there depth to eutectic solvents?. Curr. Opin. Green Sustain. Chem. 35, 100612 (2022).ArticleÂ
CASÂ
Google ScholarÂ
Goudarzi, H., Habibi, D. & Monem, A. Application of a novel deep eutectic solvent as a capable and new catalyst for the synthesis of tetrahydropyridines and 1, 3-thiazolidin-4-ones. Sci. Rep. 13, 5804 (2023).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Morrison, H. G., Sun, C. C. & Neervannan, S. Characterization of thermal behavior of deep eutectic solvents and their potential as drug solubilization vehicles. Int. J. Pharm. 378, 136–139 (2009).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Jouyban, A. Handbook of Solubility Data for Pharmaceuticals (CRC Press, 2009).BookÂ
Google ScholarÂ
Savjani, K. T., Gajjar, A. K. & Savjani, J. K. Drug solubility: Importance and enhancement techniques. Int. Sch. Res. Notices 2012, 1–10 (2012).
Google ScholarÂ
Marcus, Y. & Marcus, Y. Applications of Deep Eutectic Solvents 111–151 (Springer International Publishing, 2019).
Google ScholarÂ
Li, Z. & Lee, P. I. Investigation on drug solubility enhancement using deep eutectic solvents and their derivatives. Int. J. Pharm. 505, 283–288 (2016).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Mokhtarpour, M., Shekaari, H., Martinez, F. & Zafarani-Moattar, M. T. Study of naproxen in some aqueous solutions of choline-based deep eutectic solvents: Solubility measurements, volumetric and compressibility properties. Int. J. Pharm. 564, 197–206 (2019).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Shivagan, D., Dale, P., Samantilleke, A. & Peter, L. Electrodeposition of chalcopyrite films from ionic liquid electrolytes. Thin Solid Films 515, 5899–5903 (2007).ArticleÂ
ADSÂ
CASÂ
Google ScholarÂ
Phadtare, S. B. & Shankarling, G. S. Halogenation reactions in biodegradable solvent: Efficient bromination of substituted 1-aminoanthra-9, 10-quinone in deep eutectic solvent (choline chloride: urea). Green Chem. 12, 458–462 (2010).ArticleÂ
CASÂ
Google ScholarÂ
Sonawane, Y. A., Phadtare, S. B., Borse, B. N., Jagtap, A. R. & Shankarling, G. S. Synthesis of diphenylamine-based novel fluorescent styryl colorants by knoevenagel condensation using a conventional method, biocatalyst, and deep eutectic solvent. Org. lett. 12, 1456–1459 (2010).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Ilgen, F. & König, B. Organic reactions in low melting mixtures based on carbohydrates and L-carnitine-a comparison. Green Chem. 11, 848–854 (2009).ArticleÂ
CASÂ
Google ScholarÂ
Coulembier, O. et al. Synthesis of poly (l-lactide) and gradient copolymers from al-lactide/trimethylene carbonate eutectic melt. Chem. Sci. 3, 723–726 (2012).ArticleÂ
CASÂ
Google ScholarÂ
Ilgen, F. et al. Conversion of carbohydrates into 5-hydroxymethylfurfural in highly concentrated low melting mixtures. Green Chem. 11, 1948–1954 (2009).ArticleÂ
CASÂ
Google ScholarÂ
Knözinger, H. & Kochloefl, K. Heterogeneous catalysis and solid catalysts, Ullmann’s Encyclo-pedia of Industrial Chemistry. (2000).Toure, B. B. & Hall, D. G. Natural product synthesis using multicomponent reaction strategies. Chem. Rev. 109, 4439–4486 (2009).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Hulme, C. & Gore, V. Multi-component reactions: Emerging chemistry in drug discovery from xylocain to crixivan. Curr. Med. Chem. 10, 51–80 (2003).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Haji, M. Multicomponent reactions: A simple and efficient route to heterocyclic phospho-nates. Beilstein J. Org. Chem. 12, 1269–1301 (2016).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Cioc, R. C. & Ruijter, E. Multicomponent reactions: Advanced tools for sustainable organic synthesis. Curr. Green Chem. 16, 2958–2975 (2014).ArticleÂ
CASÂ
Google ScholarÂ
Estevez, V., Villacampa, M. & Menendez, J. C. Multicomponent reactions for the synthesis of pyrroles. Chem. Soc. Rev. 39, 4402–4421 (2010).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Ramón, D. J. & Yus, M. Asymmetric multicomponent reactions (AMCRs): The new frontier. Angew. Chem. Int. Ed. 44, 1602–1634 (2005).ArticleÂ
Google ScholarÂ
Mironov, M. A. Multicomponent reactions and combinatorial chemistry. Russ. J. Gen. Chem. 80, 2628–2646 (2020).ArticleÂ
Google ScholarÂ
Zakeri, M., Nasef, M. M., Abouzari-Lotf, E., Moharami, A. & Heravi, M. M. Sustainable alternative protocols for the multicomponent synthesis of spiro-4H-pyrans catalyzed by 4-di-methylaminopyridine. J. Indus. Engin. Chem. 29, 273–281 (2015).ArticleÂ
CASÂ
Google ScholarÂ
Groenendaal, B., Ruijter, E. & Orru, R. V. 1-Azadienes in cycloaddition and multicomponent reactions towards N-heterocycles. Chem. Commun. 43, 5474–5489 (2008).ArticleÂ
Google ScholarÂ
Zhou, B., Liu, Q., Wang, H., Jin, H. & Liu, Y. CuI/Cu (OTf)2/DMSO system-catalyzed intra-molecular oxidative cyclization of (o-alkynyl) arylketones: Efficient synthesis of 1,4-naphtho-quinones. Tetrahedron Lett. 75, 3815–3821 (2019).ArticleÂ
CASÂ
Google ScholarÂ
Dar, U. A. et al. Quantum chemical approach towards the secondary amino derivatives of C (3) substituted 1,4-naphtho-quinone: Combined molecular and dft calculations. J. Mol. Struct. 1203, 127306 (2020).ArticleÂ
CASÂ
Google ScholarÂ
Suhara, Y. et al. Synthesis of new vitamin K analogues as steroid and xenobiotic receptor (SXR) agonists: Insights into the biological role of the side chain part of vitamin K. J. Med. Chem. 54, 4918–4922 (2011).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Silva, T. M. et al. Molluscicidal activity of synthetic lapachol amino and hydrogenated derivatives. Bioorg. Med. Chem. Lett. 13, 193–196 (2005).ArticleÂ
CASÂ
Google ScholarÂ
Mäntylä, A. et al. Synthesis, in vitro evaluation, and antileishmanial activity of water-soluble prodrugs of buparvaquone. J. Med. Chem. 47, 188–195 (2004).ArticleÂ
PubMedÂ
Google ScholarÂ
Ganapaty, S., Thomas, P. S., Karagianis, G. & Waterman, P. G. Antiprotozoal and cytotoxic naphthalene derivatives from diospyros assimilis. Phytochem. 67, 1950–1956 (2006).ArticleÂ
CASÂ
Google ScholarÂ
Tandon, V. K. et al. 2,3-Disubstituted-1,4-naphthoquinones, 12H-benzo[b]phenothiazine-6,11-diones and related compounds: Synthesis and biological evaluation as potential antiproliferative and antifungal agents. Eur. J. Med. Chem. 44, 1086–1092 (2009).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Tandon, V. K. et al. Naphtho[2,3-b][1,4]-thiazine-5,10-diones and 3-substituted-1,4-dioxo-1,4-dihydronaphthalen-2-yl-thioalkan-oate derivatives: Synthesis and biological evaluation as potential antibacterial and antifungal agents. Bioorg. Med. Chem. Lett. 16, 5883–5887 (2006).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Biot, C., Bauer, H., Schirmer, R. H. & Davioud-Charvet, E. 5-Substituted tetrazoles as bioisosteres of carboxylic acids. Bioisosterism and mechanistic studies on glutathione reductase inhibitors as antimalarials. J. Med. Chem. 47, 5972–5983 (2004).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Duroux, L., Delmontte, F. M., Lancelin, J. M., Keravis, G. & Allemand, C. J. Insight into naphtho-quinone metabolism: β-glucosidase-catalysed hydrolysis of hydrojuglone β-D-gluco-pyranoside. Biochem. J. 333, 275–283 (1998).ArticleÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Marchionatti, A. M., Picotto, G., Narvaez, C. J., Welsh, J. & de Talamoni, N. G. T. Antiproliferative action of menadione and 1,25 (OH)2D3 on breast cancer cells. J. Steroid Biochem. Mol. Biol. 113, 227–232 (2009).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Weissenberg, M. et al. Effect of substituent and ring changes in naturally occurring naphthoquinones on the feeding response of larvae of the Mexican bean beetle, Epilachna varivestis. J. Chem. Ecol. 23, 3–18 (1997).ArticleÂ
CASÂ
Google ScholarÂ
Reese, S. et al. The Pin 1 inhibitor juglone attenuates kidney fibrogenesis via Pin 1-independent mechanisms in the unilateral ureteral occlusion model. Fibrogenesis Tissue Repair 3, 1–8 (2010).ArticleÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Talcott, R. E., Smith, M. T. & Giannini, D. D. Inhibition of microsomal lipid peroxidation by naphthoquinones: structure-activity relationships and possible mechanisms of action. Arch. Biochem. Biophys. 241, 88–94 (1985).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Green, G. R. et al. Comprehensive Heterocyclic Chemistry II Vol. 469 (Pergamon Press, 1995).
Google ScholarÂ
Pandit, K. S., Chavan, P. V., Desai, U. V., Kulkarni, M. A. & Wadgaonkar, P. P. Trishydroxy-methylaminomethane (THAM): A novel organocatalyst for a environmentally benign synthesis of medicinally important tetrahydrobenzo[b]pyrans and pyran-annulated heterocycles. New J. Chem. 39, 4452–4463 (2015).ArticleÂ
CASÂ
Google ScholarÂ
Adreani, L. L. & Lapi, E. n some new esters of coumarin-3-carboxylic acid wit balsamic and bronchodilator action Boll. Chim. Farm. 99, 583–586 (1960).CASÂ
Google ScholarÂ
Bonsignore, L., Loy, G., Secci, D. & Calignano, A. Synthesis and pharmacological activity of 2-oxo-(2H) 1-benzopyran-3-carboxamide derivatives. Eur. J. Med. Chem. 28, 517–520 (1993).ArticleÂ
CASÂ
Google ScholarÂ
Ghorbani-Choghamarani, A., Sahraei, R. & Taherinia, Z. Ni (II) immobilized on modified boehmite nanostructures: A novel, inexpensive, and highly efficient heterogeneous nanocatalyst for multi-component domino reactions. Res. Chem. Intermed. 5, 3199–3214 (2019).ArticleÂ
Google ScholarÂ
Mishra, A., Pandey, Y. K., Tufail, F. & Singh, J. A convenient and green synthetic approach for Benzo[a]pyrano[2,3-c]phenazines via supramolecular catalysis. Catal. Lett. 150, 1659–1668 (2020).ArticleÂ
CASÂ
Google ScholarÂ
Yan, L., Li, Y., Yang, B. & Gao, W. InBr 3-catalyzed synthesis of highly functionalized piperidines and benzo[a]pyrano[2,3-c]phenazines. Polycyclic Aromat. Compd. 42, 534–542 (2022).ArticleÂ
CASÂ
Google ScholarÂ
Ghorbani-Choghamarani, A., Mohammadi, M., Shiri, L. & Taherinia, Z. Synthesis and characterization of spinel FeAl2O4 (hercynite) magnetic nanoparticles and their application in multicomponent reactions. Res. Chem. Intermed. 45, 5705–5723 (2019).ArticleÂ
CASÂ
Google ScholarÂ
Abadi, A. Y. E., Maghsoodlou, M. T., Heydari, R. & Mohebat, R. An efficient four-component domino protocol for the rapid and green synthesis of functionalized benzo[a]pyrano[2,3-c] phenazine derivatives using caffeine as a homogeneous catalyst. Res. Chem. Intermed. 42, 1227–1235 (2016).ArticleÂ
CASÂ
Google ScholarÂ
Yazdani-Elah-Abadi, A., Maghsoodlou, M. T., Mohebat, R. & Heydari, R. Theophylline as a new and green catalyst for the one-pot synthesis of spiro[benzo[a]pyrano[2,3-c]phenazine] and benzo [a]pyrano[2,3-c]phenazine derivatives under solvent-free conditions. Chinese Chem. Lett. 28, 446–452 (2017).ArticleÂ
CASÂ
Google ScholarÂ
Naeimi, H. & Zarabi, M. F. Multisulfonate hyperbranched polyglycerol functionalized graphene oxide as an efficient reusable catalyst for green synthesis of benzo[a]pyrano-[2,3-c]phenazines under solvent-free conditions. RSC Adv. 9, 7400–7410 (2019).ArticleÂ
ADSÂ
CASÂ
PubMedÂ
PubMed CentralÂ
Google ScholarÂ
Nikoorazm, M., Khanmoradi, M. & Mohammadi, M. Guanine-La complex supported onto SBA-15: A novel efficient heterogeneous mesoporous nanocatalyst for one-pot, multi-component Tandem Knoevenagel condensation–Michael addition–cyclization Reactions. Appl. Organomet. Chem. 34, 5504 (2020).ArticleÂ
Google ScholarÂ
Daraie, M., Tamoradi, T., Heravi, M. M. & Karmakar, B. Ce immobilized 1H-pyrazole-3, 5-dicarboxylic acid (PDA) modified CoFe2O4: A potential magnetic nanocomposite catalyst towards the synthesis of diverse benzo[a]pyrano [2,3-c] phenazine derivatives. J. Mol. Struct. 1245, 131089 (2021).ArticleÂ
CASÂ
Google ScholarÂ
Hasaninejad, A. & Firoozi, S. One-pot, sequential four-component synthesis of benzo[c]pyrano- [3,2-a]phenazine, bis-benzo[c]pyrano[3,2-a]phenazine and oxospiro benzo[c]pyrano[3,2-a]phena-zine derivatives using 1,4-diazabicyclo[2.2.2]octane (DABCO) as an efficient and reusable solid base catalyst. Mol. Divers. 17, 499–513 (2013).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Rahnamafar, R., Moradi, L. & Khoobi, M. Synthesis of benzo[b]xanthene-triones and tetrahydro-chromeno[2,3-b]xanthene tetraones via three-or pseudo–five-component reactions using Fe3O4@ SiO2/PEtOx as a novel, magnetically recyclable, and eco-friendly nanocatalyst. J. Heterocycl. Chem. 57, 1825–1837 (2020).ArticleÂ
CASÂ
Google ScholarÂ
Reddy, A. V. S., Reddy, M. V. & Jeong, Y. T. Silica tungstic acid (STA) as a highly efficient and reusable catalyst for the synthesis of benzoxanthenes under solvent-free conditions in ultra-sonication. Res. Chem. Intermed. 42, 5209–5218 (2016).ArticleÂ
CASÂ
Google ScholarÂ
Khurana, J. M., Lumb, A. & Chaudhary, A. Efficient and green syntheses of 12-aryl-2,3,4,12-tetra-hydrobenzo[b]xanthene-1,6,11-triones in water and task-specific ionic liquid. Synth. Commun. 43, 2147–2154 (2013).ArticleÂ
CASÂ
Google ScholarÂ
Li, J., Lu, L. & Su, W. A new strategy for the synthesis of benzoxanthenes catalyzed by proline triflate in water. Tetrahedron Lett. 51, 2434–2437 (2010).ArticleÂ
CASÂ
Google ScholarÂ
Rahmatpour, A. Polystyrene-supported GaCl3 as a highly efficient and reusable heterogeneous Lewis acid catalyst for the three-component synthesis of benzoxanthenes. Monatsh. Chem. 144, 1205–1212 (2013).ArticleÂ
CASÂ
Google ScholarÂ
Dabiri, M., Tisseh, Z. N. & Bazgir, A. An efficient three-component synthesis of benzoxanthenes in water. J. Heterocycl. Chem. 47, 1062–1065 (2010).ArticleÂ
CASÂ
Google ScholarÂ
Safaei-Ghomi, J. & Eshteghal, F. Nano-Fe3O4/PEG/succinic anhydride: A novel and efficient catalyst for the synthesis of benzoxanthenes under ultrasonic irradiation. Ultrason. Sonochem. 38, 488–495 (2017).ArticleÂ
CASÂ
PubMedÂ
Google ScholarÂ
Du, B. et al. Efficient one-pot three-component synthesis of 3,4-dihydro-12-phenyl-2H-benzo[b]xanthene-1,6,11(12H)-trione derivatives in ionic liquid. Res. Chem. Intermed. 39, 1323–1333 (2013).ArticleÂ
CASÂ
Google ScholarÂ
Shaterian, H. R. & Azizi, K. Brønsted acidic ionic liquids catalyzed one-pot synthesis of benzoxanthene leuco-dye derivatives. Res. Chem. Intermed. 41, 409–417 (2015).ArticleÂ
CASÂ
Google ScholarÂ
Turhan, K. et al. Novel benzo- [b]xanthene derivatives: Bismuth(III) triflate-catalyzed one-pot synthesis, characterization, and acetylcholinesterase, glutathione S-transferase, and butyrylcholinesterase inhibitory properties. Arch. Pharm. 353, 2000030 (2020).ArticleÂ
CASÂ
Google ScholarÂ