The cellulose aluminum oxide composite-supported imidazolium chloroaluminate ionic liquid as a novel and stable heterogeneous catalyst

References

• Klemm, D.; Heublein, B.; Fink, H. P.; Bohn, A. Cellulose: fascinating biopolymer and sustainable raw material. Angew. Chem. Int. Ed. 2005, 44, 3358–3393.
   PubMed Web of Science ®Google Scholar
• Vekariya, R. H.; Patel, H. D. Cellulose sulfuric acid (CSA) and starch sulfuric acid (SSA) as solid and heterogeneous catalysts in green organic synthesis: recent advances. Arkivoc 2015, i, 136–159.
   Google Scholar
• Poupelin, J. P.; Saint-Rut, G.; Foussard-Blanpin, O.; Narcisse, G.; Uchida-Ernouf, G.; Lacroix, R. Synthesis and antiinflammatory properties of bis (2-hydroxy-1-naphthyl)methane derivatives I. Eur. J. Med. Chem. 1978, 13, 67–71.
   Web of Science ®Google Scholar
• Chibale, K.; Visser, M.; Schalkwyk, D. V.; Smith, P. J.; Saravanamuthu, A.; Fairlamb, A. H. Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents. Tetrahedron 2003, 59, 2289–2296.
   Web of Science ®Google Scholar
• Mulakayala, N.; Murthy, P. V. N. S.; Rambabu, D.; Aeluri, M.; Adepu, R.; Krishna, G. R.; Reddy, C. M.; Prasad, K. R. S.; Chaitanya, M.; Kumar, C. S.; Rao, M. V. B.; Pal, M. Catalysis by molecular iodine: a rapid synthesis of 1,8-dioxo-octahydroxanthenes and their evaluation as potential anticancer agents. Bioorg. Med. Chem. Lett. 2012, 22, 2186–2191.
   PubMed Web of Science ®Google Scholar
• Saint-Ruf, G.; Hieu, H. T.; Poupelin, J. P. The effect of dibenzoxanthenes on the paralyzing action of zoxazolamine. Naturwissenschaften 1975, 62, 584–585.
   PubMed Web of Science ®Google Scholar
• Knight, C. G.; Stephens, T. Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles. Biochem. J. 1989, 258, 683–687.
   PubMed Web of Science ®Google Scholar
• Ahmad, M.; King, T. A.; Ko, D. K.; Cha, B. H.; Lee, J. Performance and photo stability of xanthene and pyrromethene laser dyes in sol-gel phases. J. Phys. D: Appl. Phys. 2002, 35, 1473–1476.
   Web of Science ®Google Scholar
• Das, B.; Thirupathi, P.; Ravinder Reddy, K.; Ravikanth, B.; Nagarapu, L. An efficient synthesis of 1,8-dioxo-octahydroxanthenes using heterogeneous catalysts. Catal. Commun. 2007, 8, 535–538.
   Web of Science ®Google Scholar
• Kantevari, S.; Bantu, R.; Nagarapu, L. HClO4–SiO2 and PPA–SiO2 catalyzed efficient one-pot Knoevenagel condensation, Michael addition and cyclo-dehydration of dimedone and aldehydes in acetonitrile, aqueous and solvent free conditions: scope and limitations. J. Mol. Catal. A: Chem. 2007, 269, 53–57.
   Web of Science ®Google Scholar
• Hwan Jung, D.; Rok Lee, Y.; Hong Kim, S.; Seok Lyoo, W. New and general methods for the synthesis of arylmethylene bis(3-hydroxy-2-cyclohexene-1-ones) and xanthenediones by EDDA and In(OTf)3-catalyzed one-pot domino Knoevenagel/Michael or Koevenagel/Michael/cyclodehydration reactions. Bull. Korean Chem. Soc. 2009, 30, 1989–1995.
   Web of Science ®Google Scholar
• Wang, R. H.; Cui, B.; Zhang, W. T.; Han, G. F. Green synthesis of 1,8-dioxo-octahydroxanthene derivatives using catalytic amount of H2SO4 in water. Synth. Commun. 2010, 40, 1867–1872.
   Web of Science ®Google Scholar
• Verma, G. K.; Raghuvanshi, K.; Verma, R. K.; Dwivedi, P.; Singh, M. S. An efficient one-pot solvent-free synthesis and photophysical properties of 9-aryl/alkyl-octahydroxanthene-1,8-diones. Tetrahedron 2011, 67, 3698–3704.
   Web of Science ®Google Scholar
• Mulakayala, N.; Pavan Kumar, G.; Rambab, D.; Aeluri, M.; Basaveswara Rao, M. V.; Pal, M. A greener synthesis of 1,8-dioxo-octahydroxanthene derivatives under ultrasound. Tetrahedron Lett. 2012, 53, 6923–6926.
   Web of Science ®Google Scholar
• Shirini, F.; Ghaffari Khaligh, N. Succinimide-N-sulfonic acid: an efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions. Dyes Pigm. 2012, 95, 789–794.
   Web of Science ®Google Scholar
• Ilangovan, A.; Muralidharan, S.; Sakthivel, P.; Malayappasamy, S.; Karuppusamy, S.; Kaushik, M. P. Simple and cost effective acid catalysts for efficient synthesis of 9-aryl-1,8-dioxo-octahydroxanthene. Tetrahedron Lett. 2013, 54, 491–494.
   Web of Science ®Google Scholar
• Ghasemzadeh, M. A.; Safaei-Ghomi, J.; Zahedi, S. Fe3O4 nanoparticles: a highly efficient and easily reusable catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions. J. Serb. Chem. Soc. 2013, 78, 769–779.
   Web of Science ®Google Scholar
• Sivaguru, P.; Lalitha, A. Ceric ammonium nitrate supported HY-zeolite: an efficient catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes. Chin. Chem. Lett. 2014, 25, 321–323.
   Web of Science ®Google Scholar
• Esmaeilpour, M.; Javidi, J.; Dehghani, F.; Nowroozi Dodeji, F. Fe3O4@SiO2–imid–PMAn magnetic porous nanospheres as recyclable catalysts for the one-pot synthesis of 14-aryl- or alkyl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydroxanthene derivatives under various conditions. New J. Chem. 2014, 38, 5453–5461.
   Web of Science ®Google Scholar
• Reeve, A. M. J. Reaction of dimedone and benzaldehyde: a discovery-based lab for second-semester organic chemistry. J. Chem. Educ. 2015, 92, 582–585.
   Web of Science ®Google Scholar
• Gupta, R.; Ladage, S.; Ravishankar, L. One-pot synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by Mg-Al hydrotalcites. Chem. J. 2015, 1, 1–4.
   Google Scholar
• Bhale, P. S.; Dongare, S. B.; Mule, Y. B. An efficient synthesis of 1,8-dioxo-octahydroxanthenes catalyzed by thiourea dioxide (TUD) in aqueous media. Chem. Sci. Trans. 2015, 4, 246–250.
   Google Scholar
• Gharib, A.; Vojdani Fard, L.; Noroozi Pesyan, N.; Roshani, M. Novel catalytic synthesis of xanthene and 1,8-dioxo-octahydroxanthene derivatives using ZnO nanoparticles catalyst under green conditions. Chem. J. 2015, 1, 58–67.
   Google Scholar
• Zolfigol, M. A.; Yarie, M. Hydroxylamine-O-sulfonic acid (HOSA): as a task specific catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes under mild, green and solvent-free condition. Org. Chem. Res. 2016, 2, 1–8.
   Google Scholar
• Wilkes, J. S.; Levisky, J. A.; Wilson, R. A.; Hussey, C. L. Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis. Inorg. Chem. 1982, 21, 1263–1264.
   Web of Science ®Google Scholar
• Welton, T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem. Rev. 1999, 99, 2071–2083.
   PubMed Web of Science ®Google Scholar
• Wasserscheid, P.; Keim, W. Ionic liquids-new “solutions” for transition metal catalysis. Angew. Chem. Int. Ed. 2000, 39, 3772–3789.
   PubMed Web of Science ®Google Scholar
• Valkenberg, M. H.; DeCastro, C.; Hölderich, W. F. Immobilisation of chloroaluminate ionic liquids on silica materials. Top. Catal. 2001, 14, 139–144.
   Web of Science ®Google Scholar
• Huang, M. Y.; Wu, J. C.; Shieu, F. S.; Lin, J. J. Isomerization of endo-tetrahydrodicyclopentadiene over clay-supported chloroaluminate ionic liquid catalysts. J. Mol. Catal. A: Chem. 2010, 315, 69–75.
   Google Scholar
• Parvanak Boroujeni, K.; Jafarinasab, M. Polystyrene-supported chloroaluminate ionic liquid as a new heterogeneous Lewis acid catalyst for Knoevenagel condensation. Chin. Chem. Lett. 2012, 23, 1067–1070.
   Web of Science ®Google Scholar
• Parvanak Boroujeni, K.; Ghasemi, P. Synthesis and application of a novel strong and stable supported ionic liquid catalyst with both Lewis and Brønsted acid sites. Catal. Commun. 2013, 37, 50–54.
   Web of Science ®Google Scholar
• Chrobok, A.; Baj, S.; Pudlo, W.; Jarzebski, A. Supported hydrogensulfate ionic liquid catalysis in Baeyer–Villiger reaction. Appl. Catal. A Gen. 2009, 366, 22–28.
   Web of Science ®Google Scholar
• Lazarin, A. M.; Gushikem, Y.; de Castro, S. C. Cellulose aluminium oxide coated with organofunctional groups containing nitrogen donor atoms. J. Mater. Chem. 2000, 10, 2526–2531.
   Web of Science ®Google Scholar
• Parvanak Boroujeni, K.; Rezazadeh Shirazi, E.; Doroodmand, M. M. Synthesis of α-aminophosphonates using carbon nanotube supported imidazolium salt-based ionic liquid as a novel and environmentally benign catalyst. Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 683–688.
   Web of Science ®Google Scholar
• Jin, T. -S.; Zhang, J. -S.; Xiao, J.-C.; Wang, A. -Q.; Li, T. -S. Ultrasound-assisted synthesis of 1,8-dioxo-octahydroxanthene derivatives catalyzed by p-dodecylbenzenesulfonic acid in aqueous media. Ultrason. Sonochem. 2006, 13, 220–224.
   PubMed Web of Science ®Google Scholar
• Venkatesan, K.; Pujari, S. S.; Lahoti, R. J.; Srinivasan, K. V. An efficient synthesis of 1,8-dioxo-octahydroxanthene derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation. Ultrason. Sonochem. 2008, 15, 548–553.
   PubMed Web of Science ®Google Scholar
• Naeimi, H.; Sadat Nazifi, Z. J. A facile one-pot ultrasound assisted synthesis of 1,8-dioxo-octahydroxanthene derivatives catalyzed by Brønsted acidic ionic liquid (BAIL) under green conditions. J. Ind. Eng. Chem. 2014, 20, 1043–1049.
   Web of Science ®Google Scholar
• Anslyn, E. V.; Dougherty, D. A. Modern Physical Organic Chemistry; University Science Books: California, 2006.
   Google Scholar