journal article·2019-10

Efficient preparation of 1,8-dioxo-octahydroxanthene derivatives by recyclable cobalt-incorporated sulfated zirconia (ZrO2/SO42−/Co) nanoparticles

Mohammad Ali Nasseri, Milad Kazemnejadi, Boshra Mahmoudi, Fahimeh Assadzadeh, Seyyedeh Ameneh Alavi, Ali Allahresani

Journal of Nanoparticle Research· Volume 21· Issue 10
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Abstract

This study presents one-pot multicomponent preparation of 1,8-dioxo-octahydroxanthene derivatives under very mild conditions using cobalt-incorporated sulfated zirconia (ZrO2/SO42−/Co) as an efficient heterogeneous recyclable multifunctional nanocatalyst. The nanocatalyst was successfully characterized by FTIR, XRD, TGA, FE-SEM, TEM, ICP, and EDX analyses. The nanoparticles have a mean size of 13 nm, with a combination of the monoclinic-tetragonal crystal structure. A wide scope of aldehydes bearing different functional groups was condensed with dimedone and/or 1,3-cyclohexadione in water at room temperature with good-to-high yields at short reaction times. The catalyst can be efficiently recovered and reused several times without much loss of its activity. Besides, hot filtration test gives more insight into the heterogeneous nature of the catalyst. Finally, a plausible mechanism for this transformation was proposed.
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Research context

OpenAlex topics: Multicomponent Synthesis of Heterocycles · Chemical Synthesis and Reactions · Nanomaterials for catalytic reactions

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References (67)

Show source-provided references
1. Abbasi F, Azizi N, Abdoli-Senejani M (2017) Highly efficient synthesis of dicoumarols and xanthene derivatives in presence of Brønsted–Lewis acidic ionic liquids catalyst. J Iran Chem Soc 14:2097–210310.1007/s13738-017-1146-5 ↗
2. Aboul-Gheit AK, Gad FK, Abdel-Aleem GM, El-Desouki DS, Abdel-Hamid SM, Ghoneim SA, Ibrahim AH (2014) Pt, Re and Pt–Re incorporation in sulfated zirconia as catalysts for n-pentane isomerization. Egypt J Pet 23:303–31410.1016/j.ejpe.2014.08.006 ↗
3. Afzal O, Kumar S, Haider MR, Ali MR, Kumar R, Jaggi M, Bawa S (2015) A review on anticancer potential of bioactive heterocycle quinoline. Eur J Med Chem 97:871–91010.1016/j.ejmech.2014.07.044 ↗
4. Azizi N, Abbasi F, Abdoli-Senejani M (2018) Natural acidic ionic liquid immobilized on magnetic silica: preparation and catalytic performance in chemoselective synthesis of dicoumarols and substituted xanthene derivatives. ChemistrySelect 3:3797–380210.1002/slct.201800138 ↗
5. Bansal P, Chaudhary GR, Kaur N, Mehta SK (2015) An efficient and green synthesis of xanthene derivatives using CuS quantum dots as a heterogeneous and reusable catalyst under solvent free conditions. RSC Adv 5:8205–820910.1039/C4RA15045G ↗
6. Bansal P, Kaur N, Prakash C, Chaudhary GR (2018) ZrO2 nanoparticles: an industrially viable, efficient and recyclable catalyst for synthesis of pharmaceutically significant xanthene derivatives. Vacuum 157:9–1610.1016/j.vacuum.2018.08.018 ↗
7. Bigdeli M (2010) Clean synthesis of 1, 8-dioxooctahydroxanthenes promoted by DABCO-bromine in aqueous media. Chin Chem Lett 21:1180–118210.1016/j.cclet.2010.05.018 ↗
8. Böβ E, Hillringhaus T, Nitsch J, Klussmann M (2011) Lewis acid-catalysed one pot synthesis of substituted xanthenes. Org Biomol Chem 9:1744–174810.1039/c0ob00954g ↗
9. Chaudhary A, Khurana JM (2018) Advances in the synthesis of xanthenes: an overview. Curr Org Synth 15:341–36910.2174/1570179414666171011162902 ↗
10. Dadhania AN, Patel VK, Raval DK (2017) Ionic liquid promoted facile and green synthesis of 1, 8-dioxo-octahydroxanthene derivatives under microwave irradiation. J Saudi Chem Soc 21:S163–S16910.1016/j.jscs.2013.12.003 ↗
11. Das B, Thirupathi P, Reddy KR, Ravikanth B, Nagarapu L (2007) An efficient synthesis of 1, 8-dioxo-octahydroxanthenes using heterogeneous catalysts. Catal Commun 8:535–53810.1016/j.catcom.2006.02.023 ↗
12. Datka J, Turek AM, Jehng JM, Wachs IE (1992) Acidic properties of supported niobium oxide catalysts: an infrared spectroscopy investigation. J Catal 135:186–19910.1016/0021-9517(92)90279-Q ↗
13. Devi KS, Jayashree S (2013) Eco friendly nitration of toluene using modified zirconia. Bull Chem React Eng Catal 7:205–21410.9767/bcrec.7.3.4154.205-214 ↗
14. Ethiraj AS, Kang DJ (2012) Synthesis and characterization of CuO nanowires by a simple wet chemical method. Nanoscale Res Lett 7:7010.1186/1556-276X-7-70 ↗
15. Fan X, Hu X, Zhang X, Wang J (2005) InCl3@4H2O-promoted green preparation of xanthenedione derivatives in ionic liquids. Can J Chem 83:16–2010.1139/v04-155 ↗
16. Galadima A, Wells RPK, Anderson JA (2012) n-alkane hydroconversion over carbided molybdena supported on sulfated zirconia. Appl Petrochem Res 1:35–4310.1007/s13203-011-0004-0 ↗
17. Ghiami S, Nasseri MA, Allahresani A, Kazemnejadi M (2019) FeNi3@SiO2 nanoparticles: an efficient and selective heterogeneous catalyst for the epoxidation of olefins and the oxidation of sulfides in the presence of meta-chloroperoxybenzoic acid at room temperature. React Kinet Mech Catal 126:383–39810.1007/s11144-018-1479-9 ↗
18. Gholinejad M, Ahmadi J, Nájera C (2016) Silica microparticles supported gold and copper ferrite nanoparticles: a magnetically recyclable bimetallic catalyst for Sonogashira reaction. ChemistrySelect 1:384–39010.1002/slct.201600049 ↗
19. Hasaninejad A (2012) Silica-supported phosphorus-containing catalysts efficiently promoted synthesis of 1, 8-dioxo-octahydro-xanthenes under solvent-free conditions. Chem Sci Trans 1:233–23810.7598/cst2012.107 ↗
20. Heshmatpour F, Aghakhanpour RB (2012) Synthesis and characterization of superfine pure tetragonal nanocrystalline sulfated zirconia powder by a non-alkoxide sol–gel route. Adv Powder Technol 23:80–8710.1016/j.apt.2010.12.012 ↗
21. Ibrahim AH, Al-Shafey HI, El-Desouki D, Abdel-Azim SM, Aboul-Gheit NA (2018) Preparation of sulfated zirconia catalyst loaded by copper in nano-scale green application to synthesis of biolubricant. Egypt J Chem 61:503–51610.21608/ejchem.2018.3044.1267 ↗
22. Ikeno T, Nagano T, Hanaoka K (2017) Silicon-substituted xanthene dyes and their unique photophysical properties for fluorescent probes. Chem Asian J 12:1435–144610.1002/asia.201700385 ↗
23. Ilangovan A, Malayappasamy S, Muralidharan S, Maruthamuthu S (2011) A highly efficient green synthesis of 1, 8-dioxo-octahydroxanthenes. Chem Cent J 5:8110.1186/1752-153X-5-81 ↗
24. Jadhav SV, Jinka KM, Bajaj HC (2010) Synthesis of nopol via Prins condensation of β-pinene and paraformaldehyde catalyzed by sulfated zirconia. Appl Catal A 390:158–16510.1016/j.apcata.2010.10.005 ↗
25. Jha A, Beal J (2004) Convenient synthesis of 12H-benzo [a] xanthenes from 2-tetralone. Tetrahedron Lett 45:8999–900110.1016/j.tetlet.2004.10.046 ↗
26. Karami B, Zare Z, Eskandari K (2013) Molybdate sulfonic acid: preparation, characterization, and application as an effective and reusable catalyst for octahydroxanthene-1,8-dione synthesis. Chem Pap 67:145–154
27. Kazemnejadi M, Shakeri A, Nikookar M, Mohammadi M, Esmaeilpour M (2017) Co (II) Schiff base complex decorated on polysalicylaldehyde as an efficient, selective, heterogeneous and reusable catalyst for epoxidation of olefins in mild and self-coreductant conditions. Res Chem Intermed 43:6889–691010.1007/s11164-017-3027-z ↗
28. Kazemnejadi M, Nikookar M, Mohammadi M, Shakeri A, Esmaeilpour M (2018) Melamine-Schiff base/manganese complex with denritic structure: an efficient catalyst for oxidation of alcohols and one-pot synthesis of nitriles. J Colloid Interface Sci 527:298–31410.1016/j.jcis.2018.05.045 ↗
29. Kazemnejadi M, Mahmoudi B, Sharafi Z, Nasseri MA, Allahresani A, Esmaeilpour M (2019a) Synthesis and characterization of a new poly α-amino acid Co (II)-complex supported on magnetite graphene oxide as an efficient heterogeneous magnetically recyclable catalyst for efficient free-coreductant gram-scale epoxidation of olefins with molecular oxygen. J Organomet Chem 896:59–6910.1016/j.jorganchem.2019.05.030 ↗
30. Kazemnejadi M, Rezazadeh Z, Nasseri MA, Allahresani A, Esmaeilpour M (2019b) Imidazolium chloride-co (iii) complex immobilized on Fe3O4@SiO2 as a highly active bifunctional nanocatalyst for the copper-, phosphine-, and base-free Heck and Sonogashira reactions. Green Chem 21:1718–173410.1039/C8GC03919D ↗
31. Keshavarz M, Abdoli-Senejani M, Hojati SF, Moosavifar M (2017) Novel and highly efficient heteropoly acids for one-pot mild and green synthesis of xanthene derivatives. Org Prep Proced Int 49:549–55610.1080/00304948.2017.1384258 ↗
32. Khatri C, Mishra MK, Rani A (2010) Synthesis and characterization of fly ash supported sulfated zirconia catalyst for benzylation reactions. Fuel Process Technol 91:1288–129510.1016/j.fuproc.2010.04.011 ↗
33. Khazaei A, Moosavi-Zare AR, Mohammadi Z, Zare A, Khakyzadeh V, Darvishi G (2013) Efficient preparation of 9-aryl-1, 8-dioxo-octahydroxanthenes catalyzed by nano-TiO2 with high recyclability. RSC Adv 3:1323–132610.1039/C2RA22595F ↗
34. Kuo CW, Fang JM (2001) Synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl–carbonyl coupling reactions. Synth Commun 31:877–89210.1081/SCC-100103323 ↗
35. Li X, Nagaoka K, Simon LJ, Olindo R, Lercher JA, Hofmann A, Sauer J (2005) Oxidative activation of n-butane on sulfated zirconia. J Am Chem Soc 127:16159–1616610.1021/ja054126d ↗
36. Lonyi F, Valyon J (1996) Thermally effected structural and surface transformations of sulfated TiO2, ZrO2 and TiO2-ZrO2 catalysts. J Therm Anal Calorim 46:211–21810.1007/BF01979961 ↗
37. Marakatti VS, Shanbhag GV, Halgeri AB (2013) Sulfated zirconia; an efficient and reusable acid catalyst for the selective synthesis of 4-phenyl-1, 3-dioxane by Prins cyclization of styrene. Appl Catal A Gen 451:71–7810.1016/j.apcata.2012.11.016 ↗
38. Mishra MK, Tyagi B, Jasra RV (2004) Synthesis and characterization of nano-crystalline sulfated zirconia by sol–gel method. J Mol Catal A Chem 223:61–6510.1016/j.molcata.2003.09.040 ↗
39. Mulakayala N, Kumar GP, Rambabu D, Aeluri M, Rao MB, Pal M (2012) A greener synthesis of 1, 8-dioxo-octahydroxanthene derivatives under ultrasound. Tetrahedron Lett 53:6923–692610.1016/j.tetlet.2012.10.024 ↗
40. Naeimi H, Nazifi ZS (2013) A highly efficient nano-Fe3O4 encapsulated-silica particles bearing sulfonic acid groups as a solid acid catalyst for synthesis of 1, 8-dioxo-octahydroxanthene derivatives. J Nanopart Res 15:202610.1007/s11051-013-2026-2 ↗
41. Naidu Kalla RM, Karunakaran RS, Balaji M, Kim I (2019) Catalyst-free synthesis of xanthene and pyrimidine-fused heterocyclic derivatives at water-ethanol medium and their antioxidant properties. ChemistrySelect 4:644–64910.1002/slct.201803449 ↗
42. Nguyen HT, Lallemand MC, Boutefnouchet S, Michel S, Tillequin F (2009) Antitumor psoropermum xanthones and sarcomelicope acridones: privileged structures implied in DNA alkylation. J Nat Prod 72:527–53910.1021/np800644y ↗
43. Oloye FF, McCue AJ, Anderson JA (2016) n-heptane hydroconversion over sulfated-zirconia-supported molybdenum carbide catalysts. Appl Petrochem Res 6:341–35210.1007/s13203-016-0172-z ↗
44. Parida K, Quaschning V, Lieske E, Kemnitz E (2001) Freeze-dried promoted and unpromoted sulfated zirconia and their catalytic potential. J Mater Chem 11:1903–191110.1039/b009170g ↗
45. Patil MS, Palav AV, Khatri CK, Chaturbhuj GU (2017) Rapid, efficient and solvent-free synthesis of (un) symmetrical xanthenes catalyzed by recyclable sulfated polyborate. Tetrahedron Lett 58:2859–286410.1016/j.tetlet.2017.06.027 ↗
46. Perez RF, Canhaci SJ, Borges LE, Fraga MA (2017) One-step conversion of xylose to furfuryl alcohol on sulfated zirconia-supported Pt catalyst—balance between acid and metal sites. Catal Today 289:273–27910.1016/j.cattod.2016.09.003 ↗
47. Poursattar MA, Abdollahi S, Ezzati M, Nemati-Kande E (2018) A facile synthesis of xanthene-1, 8 (2h)-dione derivatives by using tetrapropylammonium bromide as catalyst. J Heterocyclic Chem 55:1324–133010.1002/jhet.3164 ↗
48. Reddy BM, Sreekanth PM, Lakshmanan P (2005) Sulfated zirconia as an efficient catalyst for organic synthesis and transformation reactions. J Mol Catal A Chem 237:93–10010.1016/j.molcata.2005.04.039 ↗
49. Romero AO, de Correa CM, Lodoño FB (2011) Preparation and characterization of Mg-modified zirconias as catalysts for the direct synthesis of dimethyl carbonate (DMC). Rev Fac Ing Univ Antioquia 57:14–22
50. Sadeh FN, Fatahpour M, Hazeri N, Maghsoodlou MT, Lashkari M (2017) One-pot condensation approach for the synthesis of some 1, 8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo [a, j] xanthenes using lactic acid as an efficient and eco-friendly catalyst. Acta Chem Iasi 25:24–3710.1515/achi-2017-0004 ↗
51. Safari J, Aftabi P, Ahmadzadeh M, Sadeghi M, Zarnegar Z (2017) Sulfonated starch nanoparticles: an effective, heterogeneous and bio-based catalyst for synthesis of 14-aryl-14-H-dibenzo [a, j] xanthenes. J Mol Struct 1142:33–3910.1016/j.molstruc.2017.02.095 ↗
52. Salavati-Niasari M, Khansari A, Davar F (2009) Synthesis and characterization of cobalt oxide nanoparticles by thermal treatment process. Inorg Chim Acta 362:4937–494210.1016/j.ica.2009.07.023 ↗
53. Sardarian AR, Kazemnejadi M, Esmaeilpour M (2019) Bis-salophen palladium complex immobilized on Fe3O4@SiO2 nanoparticles as a highly active and durable phosphine-free catalyst for Heck and copper-free Sonogashira coupling reactions. Dalton Trans 48:3132–314510.1039/C9DT00060G ↗
54. Sarkar D, Mohapatra D, Ray S, Bhattacharyya S, Adak S, Mitra N (2007) Synthesis and characterization of sol–gel derived ZrO2 doped Al2O3 nanopowder. Ceram Int 33:1275–128210.1016/j.ceramint.2006.05.002 ↗
55. Sarma RJ, Baruah JB (2005) One step synthesis of dibenzoxanthenes. Dyes Pigments 64:91–9210.1016/j.dyepig.2004.03.010 ↗
56. Seyyedhamzeh M, Mirzaei P, Bazgir A (2008) Solvent-free synthesis of aryl-14H-dibenzo [a, j] xanthenes and 1, 8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst. Dyes Pigments 76:836–83910.1016/j.dyepig.2007.02.001 ↗
57. Sharghi H, Ebrahimpourmoghaddam S, Doroodmand MM (2013) Facile synthesis of 5-substituted-1H-tetrazoles and 1-substituted-1H-tetrazoles catalyzed by recyclable 4′-phenyl-2, 2′: 6′, 2 ″-terpyridine copper (II) complex immobilized onto activated multi-walled carbon nanotubes. J Organomet Chem 738:41–4810.1016/j.jorganchem.2013.04.013 ↗
58. Shi G, Yu F, Wang Y, Pan D, Wang H, Li R (2016) A novel one-pot synthesis of tetragonal sulfated zirconia catalyst with high activity for biodiesel production from the transesterification of soybean oil. Renew Energy 92:22–2910.1016/j.renene.2016.01.094 ↗
59. Shirini F, Langarudi MSN, Seddighi M, Jolodar OG (2015) Bi-SO3H functionalized ionic liquid based on DABCO as a mild and efficient catalyst for the synthesis of 1, 8-dioxo-octahydro-xanthene and 5-arylmethylene-pyrimidine-2, 4, 6-trione derivatives. Res Chem Intermed 41:8483–849710.1007/s11164-014-1905-1 ↗
60. Suja AH, Sugunan S (2003) Iron promoted sulphated zirconia systems as efficient catalysts for phenol hydroxylation. Bull Catal Soc India 2:194–203
61. Tang BC, Wang M, Ma JT, Wang ZX, Wu YD, Wu AX (2018) Palladium-acid co-catalyzed cleavage of alkynoates to construct dibenzo [c, h] xanthene derivatives. Adv Synth Catal 360:4023–402810.1002/adsc.201800770 ↗
62. Venkatesan K, Pujari SS, Lahoti RJ, Srinivasan KV (2008) An efficient synthesis of 1, 8-dioxo-octahydro-xanthene derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation. Sonochemistry 15:548–55310.1016/j.ultsonch.2007.06.001 ↗
63. Yan GX, Wang A, Wachs IE, Baltrusaitis J (2019) Critical review on the active site structure of sulfated zirconia catalysts and prospects in fuel production. Appl Catal A Gen 572:210–22510.1016/j.apcata.2018.12.012 ↗
64. Yang H, Hu Y, Zhang X, Qiu G (2004) Mechanochemical synthesis of cobalt oxide nanoparticles. Mater Lett 58:387–38910.1016/S0167-577X(03)00507-X ↗
65. Yang K, Li H, Zhao S, Lai S, Lai W, Lian Y, Fang W (2018) Improvement of activity and stability of CuGa promoted sulfated zirconia catalyst for n-butane isomerization. Ind Eng Chem Res 57:3855–386510.1021/acs.iecr.7b04590 ↗
66. Zhang ZH, Tao XY (2008) 2, 4, 6-Trichloro-1, 3, 5-triazine-promoted synthesis of 1, 8-dioxo-octahydroxanthenes under solvent-free conditions. Aust J Chem 61:77–7910.1071/CH07274 ↗
67. Zhang Q, Su H, Luo J, Wei Y (2012) A magnetic nanoparticle supported dual acidic ionic liquid: a “quasi-homogeneous” catalyst for the one-pot synthesis of benzoxanthenes. Green Chem 14:201–20810.1039/C1GC16031A ↗