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Phospho sulfonic acid as efficient heterogeneous Brønsted acidic catalyst for one-pot synthesis of 14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes

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An Erratum to this article was published on 08 February 2017

Abstract

A simple, efficient procedure for the preparation of phospho sulfonic acid PO(OSO3H)3 as a Brønsted acidic and recoverable heterogeneous catalyst is described, used for the one-pot synthesis of aryl-14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes. A cost-effective, simple and convenient procedure for the synthesis of aryl-14H-dibenzo[a,j]xanthenes was developed via a one-pot condensation from substituted benzaldehydes and β-naphthol under solvent-free conditions. The one-pot condensation of substituted benzaldehydes and 5,5-dimethyl-1,3-cyclohexanedione (dimedone) under solvent-free conditions leads to 1,8-dioxo-octahydro-xanthenes. These protocols afford a number of advantages, such as: excellent yields, very short reaction times, easy procedure, simple methodology and ease of preparation and regeneration of the catalyst.

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References

  • Ahmad, M., King, T. A., Ko, D. K., Cha, B.H., & Lee, J. M. (2002). Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases. Journal of Physics D: Applied Physics, 35, 1473–1476. DOI: 10.1088/0022-3727/35/13/303.

    Article  CAS  Google Scholar 

  • Bigdeli, M. A., Heravi, M. M., & Mahdavinia, G. H. (2007). Silica supported perchloric acid (HClO4-SiO2): A mild, reusable and highly efficient heterogeneous catalyst for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes. Journal of Molecular Catalalysis A: Chemical, 275, 25–29. DOI: 10.1016/j.molcata.2007.05.007.

    Article  CAS  Google Scholar 

  • Carrigan, M. D., Eash, K. J., Oswald, M. C., & Mohan, R. S. (2001). An efficient method for the chemoselective synthesis of from aromatic aldehydes using bismuth trifiate. Tetrahedron Letters, 42, 8133–8135. DOI: 10.1016/s0040-4039(01)01756-7.

    Article  CAS  Google Scholar 

  • Dabiri, M., Azimi, S. C., & Bazgir, A. (2008). One-pot synthesis of xanthene derivatives under solvent-free conditions. Chemical Papers, 62, 522–526. DOI: 10.2478/s11696-008-0050-y.

    Article  CAS  Google Scholar 

  • Das, B., Ravikanth, B., Ramu, R., Laxminarayana, K., & Rao, B. V. (2006). Iodine catalyzed simple and efficient synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes. Journal of Molecular Catalalysis A: Chemical, 255, 74–77. DOI: 10.1016/j.molcata.2006.04.007.

    Article  CAS  Google Scholar 

  • Dupont, J., de Souza, R. F., & Suarez, P. A. Z. (2002). Ionic liquid (molten salt) phase organometallic catalysis. Chemical Reviews, 102, 3667–3692. DOI: 10.1021/cr010338r.

    Article  CAS  Google Scholar 

  • Hajipour, A. R., Khazdooz, L., & Ruoho, A. E. (2008). Brønsted acidic ionic liquid as an efficient catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions. Catalysis Communications, 9, 89–96. DOI: 10.1016/j.catcom.2007.05.003.

    Article  CAS  Google Scholar 

  • Hajinasiri, R., & Rezayati, S. (2013). Solvent-free synthesis of 1,2-disubstituted derivatives of 1,2-dihydroisoquinoline, 1,2 dihydroquinoline and 1,2-dihydropyridine. Zeitschrift für Naturforschung B, 68, 818–822. DOI: 10.5560/znb.2013-3095.

    Article  CAS  Google Scholar 

  • Hasaninejad, A., Dadar, M., & Zare, A. (2012). Silica-supported phosphorus containing catalysts efficiently promoted synthesis of 1,8-dioxo-octahydro-xanthenes under solvent-free conditions. Chemical Science Transactions, 1, 233–238. DOI: 10.7598/cst2012.107.

    Article  Google Scholar 

  • Horning, E. C., & Horning, M. G. (1964). Methone derivatives of aldehydes. The Journal of Organic Chemistry, 11, 95–99. DOI: 10.1021/jo01171a014.

    Article  Google Scholar 

  • Jha, A., & Beal, J. (2004). Convenient synthesis of 12H-benzo[a]xanthenes from 2-tetralone. Tetrahedron Letters, 45, 8999–9001. DOI: 10.1016/j.tetlet.2004.10.046.

    Article  CAS  Google Scholar 

  • Jin, T. S., Zhang, J. S., Xiao, J. C., Wang, A. Q., & Li, T. S. (2004). Clean synthesis of 1,8-dioxo-octahydroxanthene derivatives catalyzed by p-dodecylbenezenesulfonic acid in aqueous media. Synlett, 5, 866–870. DOI: 10.1055/s-2004-820022.

    Article  Google Scholar 

  • Jin, T. S., Zhang, J. S., Wang, A. Q., & Li, T. S. (2005). Solid-state condensation reactions between aldehydes and 5,5-dimethyl-1,3-cyclohexanedione by grinding at room temperature. Synthetic Communications, 35, 2339–2345. DOI: 10.1080/00397910500187282.

    Article  CAS  Google Scholar 

  • 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. Chemical Papers, 67, 145–154. DOI: 10.2478/s11696-012-0263-y.

    CAS  Google Scholar 

  • Khosropour, A. R., Khodaei, M. M., & Moghannian, H. (2005). A facile, simple and convenient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j]xanthenes catalyzed by pTSA in solution and solvent-free conditions. Synlett, 6, 955–958. DOI: 10.1055/s-2005-864837.

    Article  Google Scholar 

  • Kiasat, A. R., & Fallah-Mehrjardi, M. (2008). B(HSO4)3: A novel and efficient solid acid catalyst for the regioselective conversion of epoxides to thiocyanohydrins under solvent-free conditions. Journal of the Brazilian Chemical Society, 19, 1595–1599. DOI: 10.1590/s0103-50532008000800020.

    Article  CAS  Google Scholar 

  • Kiasat, A. R., Mouradzadegun, A., & Saghanezhad, S. J. (2013). Phospho sulfonic acid: A novel and efficient solid acid catalyst for the one-pot preparation of indazolo[1,2-b]-phthalazinetriones. Journal of the Serbian Chemical Society, 78, 469–476. DOI: 10.2298/jsc120508088k.

    Article  CAS  Google Scholar 

  • Kitahara, Y., & Tanaka, K. (2002). Synthesis, crystal structure and properties of thiaheterohelicenes containing phenolic hydroxy functions. Chemical Communications, 2002, 932–933. DOI: 10.1039/b110514k.

    Article  Google Scholar 

  • Knight, C. G., & Stephens, T. (1989). Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles. Biochemical Journal, 258, 683–687.

    Article  CAS  Google Scholar 

  • Knignt, D. W., & Little, P. B. (1998). The first high-yielding benzyne cyclization using a phenolic nucleophile: A new route to xanthenes. Synlett, 1998, 1141–1143. DOI: 10.1055/s-1998-1878.

    Article  Google Scholar 

  • Ko, S. K., & Yao, C. F. (2006). Heterogeneous catalyst: Amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes under solvent-free conditions. Tetrahedron Letters, 47, 8827–8829. DOI: 10.1016/j.tetlet.2006.10.072.

    Article  CAS  Google Scholar 

  • Kumar, P. S., Sunil Kumar, B., Rajitha, B., Narsimha Reddy, P., Sreenivasulu, N., & Thirupathi Reddy, Y. (2006). A novel one pot synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes catalyzed by selectfluor™ under solvent free conditions. Arkivoc, 2006, 46–50. DOI: 10.3998/ark.5550190.0007.c05.

    Google Scholar 

  • Kumar, R., Nandi, G. C., Verma, R. K., & Singh, M. S. (2010). A facile approach for the synthesis of 14-aryl- or alkyl-14H-dibenzo[a,j]xanthenes under solvent-free condition. Tetrahedron Letters, 51, 442–445. DOI: 10.1016/j.tetlet.2009.11.064.

    Article  CAS  Google Scholar 

  • Kuo, C. W., & Fang, J. M. (2001). Synthsis of xanthnes, indanes and tetrahydronaphthalenes via intramolecular phenyl-carbonyl coupling reactions. Synthetic Communications, 31, 877–892. DOI: 10.1081/scc-100103323.

    Article  CAS  Google Scholar 

  • Lambert, R. W., Martin, J. A., Merrett, J. H., Parkes, K. E. B., & Thomas, G. J. (1997). International Patent No. WO9706178. The International Patent System.

  • Mokhtary, M., & Refahati, S. (2013). Polyvinylpolypyrrolidone-supported boron trifluoride (PVPP-BF3): Mild and efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j] xanthenes and bis(naphthalen-2-yl-sulfane) derivatives. Dyes and Pigments, 99, 378–381. DOI: 10.1016/j.dyepig.2013.05.023.

    Article  CAS  Google Scholar 

  • Madhav, J. V., Kuarm, B. S., & Rajitha, B. (2008). Dipyridine cobalt chloride: A novel and efficient catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions. Arkivoc, 2008, 204–209. DOI: 10.3998/ark.5550190.0009.222.

    Article  Google Scholar 

  • Mahdavinia, G. H., Rostamizadeh, S., Amani, A. M., & Emdadi, Z. (2009). Ultrasound-promoted greener synthesis of aryl-14H-dibenzo[a,j]xanthenes catalyzed by NH4H2PO4/SiO2 in water. Ultrasonics sonochemistry, 16, 7–10. DOI: 10.1016/j.ultsonch.2008.05.010.

    Article  CAS  Google Scholar 

  • Nagarapu, L., Kantevari, S., Mahankhali, V. C., & Apuri, S. (2007). Potassium dodecatungsto cobaltate trihydrate (K5CoW12O40 · 3H2O): A mild and efficient reusable catalyst for the synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and microwave irradiation. Catalysis Communications, 8, 1173–1177. DOI: 10.1016/j.catcom.2006.11.003.

    Article  CAS  Google Scholar 

  • Nazari, S., Keshavarz, M., Karami, B., Iravani, N., & Vafaee-Nezhad, M. (2014). Imidazol-1-yl-acetic acid as a novel green bifunctional organocatalyst for the synthesis of 1,8-dioxooctahydroxanthenes under solvent-free conditions. Chinese Chemical Letters, 25, 317–320. DOI: 10.1016/j.cclet.2013.12.011.

    Article  CAS  Google Scholar 

  • Pasha, M. A., & Jayashankara, V. P. (2007). Molecular iodine catalyzed synthesis of aryl-14H-dibenzo[a,j]xanthenes under solvent-free condition. Bioorganic & Medicinal Chemistry Letters, 17, 621–623. DOI: 10.1016/j.bmcl.2006.11.009.

    Article  CAS  Google Scholar 

  • Patil, S. B., Bhat, R. P., & Samant, S. D. (2006). Cation exchange resins: Efficient heterogeneous catalysts for facile synthesis of dibenzoxanthene from β-naphthol and aldehydes. Synthetic Communications, 36, 2163–2168. DOI: 10.1080/00397910600639372.

    Article  Google Scholar 

  • Poupelin, J. P., Saint-Ruf, G., Foussard-Blanpin, O., Narcisse, G., Uchida-Ernouf, G., & Lacroix, R. (1978). Synthesis and anti inflammatory properties of bis (2-hydroxy-1-naphthyl)methane derivatives. European Journal of Medicinal Chemistry, 13, 67–71.

    CAS  Google Scholar 

  • Rajitha, B., Kumar, B. S., Reddy, Y. T., Reddy, P. N., & Sreenivasulu, N. (2005). Sulfamic acid: A novel and efficient catalyst for the synthesis of aryl-14H-dibenzo[a,j]xanthenes under conventional heating and microwave irradiation. Tetrahedron Letters, 46, 8691–8693. DOI: 10.1016/j.tetlet.2005.10.057.

    Article  CAS  Google Scholar 

  • Rao, G. B. D., Kaushik, M. P., & Halve, A. K. (2012). An efficient synthesis of naphtha[1,2-e]oxazinone and 14-substituted-14H-dibenzo[a,j]xanthene derivatives promoted by zinc oxide nanoparticle under thermal and solventfree conditions. Tetrahedron Letters, 53, 2741–2744. DOI: 10.1016/j.tetlet.2012.03.085.

    Article  Google Scholar 

  • Rezayati, S., Hajinasiri, R., Erfani, Z., Rezayati, S., & Afshari-Sharifabad, S. (2014). Boric acid as a highly efficient and reusable catalyst for the one-pot synthesis of 1,8-dioxo-octahydroxanthenes under solvent-free conditions. Iranian Journal of Catalysis, 4, 157–162.

    Google Scholar 

  • Saini, A., Kumar, S., & Sandhu, J. S. (2006). A new LiBr-catalyzed, facile and efficient method for the synthesis of 14-alkyl or aryl-14H-dibenzo[a,j]xanthenes and tetrahy-drobenzo[b]pyrans under solvent-free conventional and microwave heating. Synlett, 2006, 1928–1932. DOI: 10.1055/s-2006-947339.

    Article  Google Scholar 

  • Sajjadifar, S., & Rezayati, S. (2014). Synthesis of 1,1-diacetates catalysed by silica-supported boron sulfonic acid under solvent-free conditions and ambient temperature. Chemical Papers, 68, 531–539. DOI: 10.2478/s11696-013-0480-z.

    Article  CAS  Google Scholar 

  • Sarkar, A., Roy, S. R., Parikh, N., & Chakraborti, A. K. (2011). Nonsolvent application of ionic liquids: organo-catalysis by 1-alkyl-3-methylimidazolium cation based room-temperature ionic liquids for chemoselective N-tert-butyloxycarbonylation of amines and the influence of the C-2 hydrogen on catalytic efficiency. The Journal of Organic Chemistry, 76, 7132–7140. DOI: 10.1021/jo201102q.

    Article  CAS  Google Scholar 

  • 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 and Pigments, 76, 836–839. DOI: 10.1016/j.dyepig.2007.02.001.

    Article  CAS  Google Scholar 

  • Shakibaei, G. I., Mirzaei, P., & Bazgir, A. (2007). Dowex-50W promoted synthesis of 14-aryl-14H-dibenzo[a,j]xanthene and 1,8-dioxo-octahydroxanthene derivatives under solvent-free conditions. Applied Catalalysis A: General, 325, 188–192. DOI: 10.1016/j.apcata.2007.03.008.

    Article  CAS  Google Scholar 

  • Shaterian, H. R., Ghashang, M., & Mir, N. (2007). Aluminium hydrogensulfate as an efficient and heterogeneous catalyst for preparation of aryl 14H-dibenzo[a,j]xanthene derivatives under thermal and solvent-free conditions. Arkivoc, 2007, 1–10. DOI: 10.3998/ark.5550190.0008.f01.

    Google Scholar 

  • Shirini, F., & Khaligh, N. G. (2012). Succinimide-N-sulfonic acid: An efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions. Dyes and Pigments, 95, 789–794. DOI: 10.1016/j.dyepig.2012.06.022.

    Article  CAS  Google Scholar 

  • Shirini, F., Yahyazadeh, A., & Mohammadi, K. (2014). One-pot synthesis of various xanthene derivatives using ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable catalyst under solvent-free conditions. Chinese Chemical Letters, 25, 341–347. DOI: 10.1016/j.cclet.2013.11.016.

    Article  CAS  Google Scholar 

  • Sivaguru, P., & Lalitha, A. (2014). Ceric ammonium nitrate supported HY-zeolite: An efficient catalyst for the synthesis of 1,8-dioxo-octahydroxanthenes. Chinese Chemical Letters, 25, 321–323. DOI: 10.1016/j.cclet.2013.11.043.

    Article  CAS  Google Scholar 

  • Song, G. Y., Wang, B., Luo, H. T., & Yang, L. M. (2007). Fe3+-montmorillonite as a cost effective and recyclable solid acidic catalyst for the synthesis of xanthenediones. Catalysis Communications, 8, 673–676. DOI: 10.1016/j.catcom.2005.12.018.

    Article  CAS  Google Scholar 

  • Takeshiba, H., & Jiyoujima, T. (1981). Japan Patent No. 56005480. Tokyo, Japan: Japan Patent Office.

  • Tayebee, R., & Tizabi, S. (2012) Highly efficient and environmentally friendly preparation of 14-aryl-14H dibenzo[a,j]xanthenes catalyzed by tungsto-divanado-phosphoric acid. Chinese Journal of Catalysis, 33, 962–969.

    Article  CAS  Google Scholar 

  • Tisseh, Z. N., Azimi, S. C., Mirzaei, P., & Bazgir, A. (2008). The efficient synthesis of aryl-5H-dibenzo[b,i]xanthene-5,7,12,14 (13H)-tetraone leuco-dye derivatives. Dyes and Pigments, 79, 273–275. DOI: 10.1016/j.dyepig.2008.04.001.

    Article  CAS  Google Scholar 

  • Wang J. Q., & Harvey, G. R. (2002). Synthesis ofpolycyclic xanthenes and furans via palladium catalyzed cyclization of polycyclic aryltriflate esters. Tetrahedron, 58, 5927–5931. DOI: 10.1016/s1872-2067(11)60387-2.

    Article  CAS  Google Scholar 

  • Zareyee, D., Alizadeh, P., Ghandali, M. S., & Khalilzadeh, M. A. (2013). Solvent-free acetylation and tetrahydropyranylation of alcohols catalyzed by recyclable sulfonated ordered nanostructured carbon. Chemical Papers, 67, 713–721. DOI: 10.2478/s11696-013-0369-x.

    Article  CAS  Google Scholar 

  • Zareyee, D., & Serehneh, M. (2014). Recyclable CMK-5 supported sulfonic acid as an environmentally benign catalyst for solvent-free one-pot construction of coumarin through Pechmann condensation. Journal of Molecular Catalysis A: Chemical, 391, 88–91. DOI: 10.1016/j.molcata.2014.04.013.

    Article  CAS  Google Scholar 

  • Zhang, Z. H., & Liu, Y. H. (2008). Antimony trichloride/SiO2 promoted synthesis of 9-ary-3,4,5,6,7,9-hexahydroxanthene-1,8-diones. Catalysis Communications, 9, 1715–1719. DOI: 10.1016/j.catcom.2008.01.031.

    Article  CAS  Google Scholar 

  • Zolfigol, M. A., Vahedi, H., Massoudi, A., Sajjadifar, S., Louie, O., & Javaherneshan, N. (2011). Mild and efficient one pot synthesis of benzimidazoles from aldehydes by using BSA as a new catalyst. Clinical Biochemistry, 44, S219. DOI: 10.1016/j.clinbiochem.2011.08.973.

    Article  Google Scholar 

  • Zolfigol, M. A., Khakyzadeh, V., Moosavi-Zare, A. R., Zare, A., Azimi, S. B., Asgari, Z., & Hasaninejad, A. (2012). Preparation of various xanthene derivatives over sulfonic acid functionalized imidazolium salts (SAFIS) as novel, highly efficient and reusable catalysts. Comptes Rendus Chimie, 15, 719–736. DOI: 10.1016/j.crci.2012.05.003.

    Article  CAS  Google Scholar 

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  1. Chemistry Department, Qaemshahr Branch, Islamic Azad University, PO BOX 163, Qaemshahr, Iran

    Sobhan Rezayati, Zahra Erfani & Rahimeh Hajinasiri

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  1. Sobhan Rezayati
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  2. Zahra Erfani
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A corrigendum to this article is available at http://dx.doi.org/10.1007/s11696-017-0134-7.

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Rezayati, S., Erfani, Z. & Hajinasiri, R. Phospho sulfonic acid as efficient heterogeneous Brønsted acidic catalyst for one-pot synthesis of 14H-dibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes. Chem. Pap. 69, 536–543 (2015). https://doi.org/10.1515/chempap-2015-0058

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