Home Facile and efficient synthesis of xanthenedione derivatives promoted by niobium pentachloride
Article
Licensed
Unlicensed Requires Authentication

Facile and efficient synthesis of xanthenedione derivatives promoted by niobium pentachloride

  • Willian H. dos Santos and Luiz C. Da Silva-Filho EMAIL logo
Published/Copyright: September 28, 2016
Become an author with De Gruyter Brill

Abstract

Xanthenedione derivatives were synthesised in one-pot reactions between arylaldehyde derivatives and 1, 3-cyclohexanedione promoted by niobium pentachloride. This new method is simple, cost-effective, high-yielding with a good variety of substrates generality, and can be conducted within reasonable reaction times.

Acknowledgements

The authors would like to thank Fundação de Amparo á Pesquisa do Estado de São Paulo (FAPESP), Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq), Coordenadoria de Aperfeiçoamento de Pessoal do Nível Superior (CAPES), and Pró-Reitoria de Pesquisa da UNESP (PROPe-UNESP) for their financial support. The authors would also like to thank CBMM – Companhia Brasileira de Metalurgia e Mineração for the NbCl5 samples. The authors would also like to express their special thanks to N. B. Dias and M. S. Palma from the São Paulo State University in Rio Claro for their HR-MS analyses, and to Bannach, G., Guerra, R. B., Ferreira, L. T. and Alarcon, R. T. for their DSC analyses.

Supplementary data

Supplementary data associated with this article can be found in the online version of this paper (DOI: 10.1515/chempap-2016-0098).

References

Ahmad, M., King, T. A., Ko, D. K., Cha, B. H., & Lee, J. (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.Search in Google Scholar

Alves, O. L. (1986). Técnicas de síntese em atmosfera inerte. Química Nova, 9, 276–281. (in Portuguese)Search in Google Scholar

Andrade, C. K. Z. (2004). Niobium pentachloride in organic synthesis: Applications and perspectives. Current Organic Synthesis, 1, 333-353.10.1002/chin.200506254Search in Google Scholar

ASTM (2014). Standard test method for purity by differential scanning calorimetry. West Conshohocken, PA, USA: ASTM International. 10.1520/e0928-08r14.Search in Google Scholar

Bartolomeu, A. A., Menezes, M. L., & Silva-Filho, L. C. (2014). Efficient one-pot synthesis of 14-aryl-14H-dibenzo [a, j]xanthene derivatives promoted by niobium pentachloride. Chemical Papers, 68, 1593–1600. DOI 10.2478/s11696-014-0597-8.Search in Google Scholar

Bartolomeu, A. A., Menezes, M. L., & Silva-Filho, L. C. (2015). Chemoselective condensation of β-naphthol, dimethyl malonate, and aromatic aldehydes promoted by niobium pentachloride. Synthetic Communications, 45, 1114—1126. 10.1080/00397911.2014.999341.Search in Google Scholar

Bekaert, A., Andrieux, J., & Plat, M. (1992). New total synthesis of bikaverin. Tetrahedron Letters, 33, 2805–2806. 10.1016/s0040-4039(00)78863-0.Search in Google Scholar

Bhowmik, B. B., & Ganguly, P. (2005). Photophysics of xanthene dyes in surfactant solution. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 61, 1997–2003. 10.1016/j.saa.2004.07.031.Search in Google Scholar

Cao, Y., Yao, C., Qin, B., & Zhang, H. (2013). Solvent-free synthesis of 14-aryl-14H-dibenzo[a, j]xanthenes catalyzed by recyclable and reusable iron(III) triflate. Research on Chemical Intermediates, 39, 3055–3062. 10.1007/s11164-012-0818-0.Search in Google Scholar

Chibale, K., Visser, M., van Schalkwyk, D., Smith, P. J., Saravanamuthu, A., & Fairlamb, A. H. (2003). Exploring the potential of xanthene derivatives as trypanothione reductase inhibitors and chloroquine potentiating agents. Tetrahedron, 59, 2289–2296. 10.1016/s0040-4020(03)00240-0.Search in Google Scholar

Dharma Rao, G. B., 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. 10.1016/j.tetlet.2012.03.085.Search in Google Scholar

D’Souza, D. M., & Müller, T. J. J. (2007). Multi-component syntheses of heterocycles by transition-metal catalysis. Chemical Society Reviews, 36, 1095–1108. 10.1039/b608235c.Search in Google Scholar PubMed

El-Brashy, A. M., El-Sayed Metwally, M., & El-Sepai, F. A. (2004). Spectrophotometric determination of some fluoroquinolone antibacterials by binary complex formation with xanthene dyes. II Farmaco, 59, 809–817. 10.1016/j.farmac.2004.07.001.Search in Google Scholar PubMed

Fobane, L., Ndam, E. N., & Mbolo, M. J. (2014). Population structure and natural regeneration of Allanblackia floribunda oliv. (Clusiaceae) in a forest concession of East Cameroon. Journal of Biodiversity and Environmental Sciences, 4, 403–408.Search in Google Scholar

Fuller, R. W., Blunt, J. W., Boswell, J. L., Cardellina, J. H., & Boyd, M. R. (1999). Guttiferone F, the first prenylated benzophenone from Allanblackia stuhlmannii. Journal of Natural Products, 62, 130–132. 10.1021/np9801514.Search in Google Scholar PubMed

Hiranrat, A., & Mahabusarakam, W. (2008). New acylphloroglucinols from the leaves of Rhodomyrtus tomentosa. Tetrahedron, 64, 11193–11197. 10.1016/j.tet.2008.09.054.Search in Google Scholar

Hiranrat, A., Chitbankluoi, W., Mahabusarakam, W., Limsuwan, S., & Voravuthikunchai, S. P. (2012). A new flavellagic acid derivative and phloroglucinol from Rhodomyrtus tomentosa. Natural Product Research, 26, 1904–1909. 10.1080/14786419.2011.628666.Search in Google Scholar PubMed

Hou, J. T., Gao, J. W., & Zhang, Z. H. (2010a). NbCl5: an efficient catalyst for one-pot synthesis of α-aminophosphonates under solvent-free conditions. Applied Organometallic Chemistry, 25, 47–53. 10.1002/aoc.1687.Search in Google Scholar

Hou, J. T., Liu, Y. H., & Zhang, Z. H. (2010b). NbCl5 as an efficient catalyst for rapid synthesis of quinoxaline derivatives. Journal of Heterocyclic Chemistry, 47, 703–706. 10.1002/jhet.388.Search in Google Scholar

Hou, J. T., Chen, H. L., & Zhang, Z. H. (2011a). Rapid and efficient trimethylsilyl protection of hydroxyl groups catalyzed by niobium(V) chloride. Phosphorus, Sulfur, and Silicon and the Related Elements, 186, 88–93. 10.1080/10426507.2010.482544.Search in Google Scholar

Hou, J. T., Gao, J. W., & Zhang, Z. H. (2011b). An efficient and convenient protocol for the synthesis of diaminotriarylmethanes. Monatshefte für Chemie – Chemical Monthly, 142, 495–499. 10.1007/s00706-011-0461-2.Search in Google Scholar

Horning, E. C., & Horning, M. G. (1946). Methone derivatives of aldehydes. The Journal of Organic Chemistry, 11, 95–99. 10.1021/jo01171a014.Search in Google Scholar PubMed

Ilangovan, A., Malayappasamy, S., Muralidharan, S., & Maruthamuthu, S. (2011). A highly efficient green synthesis of 1, 8-dioxo-octahydroxanthenes. Chemistry Central Journal, 5, 81. 10.1186/1752-153x-5-81.Search in Google Scholar PubMed PubMed Central

Iniyavan, P., Sarveswari, S., & Vijayakumar, V. (2015). Microwave-assisted clean synthesis of xanthenes and chromenes in [bmim][PF6] and their antioxidant studies. Research on Chemical Intermediates, 41, 7413–7426. 10.1007/s11164-014-1821-4.Search in Google Scholar

Isambert, N., & Lavilla, R. (2008). Heterocycles as key substrates in multicomponent reactions: The fast lane towards molecular complexity. Chemistry – A European Journal, 14, 8444–8454. 10.1002/chem.200800473.Search in Google Scholar PubMed

John, A., Yadav, P. J. P., & Palaniappan, S. (2006). Clean synthesis of 1, 8-dioxo-dodecahydroxanthene derivatives catalyzed by polyaniline-p-toluenesulfonate salt in aqueous media. Journal of Molecular Catalysis A: Chemical, 248, 121–125. 10.1016/j.molcata.2005.12.017.Search in Google Scholar

Karami, B., Zare, Z., & Eskandari, K. (2013a). Molybdate sulfonic acid: preparation, characterization, and application as an effective and reusable catalyst for octahydroxanthene-1, 8-dione synthesis. Chemical Papers, 67, 145–154. 10.2478/s11696-012-0263-y.Search in Google Scholar

Karami, B., Eskandari, K., Gholipour, S., & Jamshidi, M. (2013b). Facile and rapid synthesis of 9-aryl 1, 8-dioxoöctahydroxanthenes derivatives using tungstate sulfuric acid. Organic Preparations and Procedures International: The New Journal for Organic Synthesis, 45, 220–226. 10.1080/00304948.2013.764790.Search in Google Scholar

Karami, B., Eskandari, K., Zare, Z., & Gholipour, S. (2014). A new access to 1, 8-dioxooctahydroxanthenes using yttrium(III) nitrate hexahydrate and tin(II) chloride dihydrate as effective and reusable catalysts. Chemistry of Heterocyclic Compounds, 49, 1715–1722. 10.1007/s10593-014-1423-5.Search in Google Scholar

Kaya, M., Basar, E., & Colak, F. (2011). Synthesis and antimicrobial activity of some bisoctahydroxanthene-1, 8-dione derivatives. Medicinal Chemistry Research, 20, 1214–1219. 10.1007/s00044-010-9459-2.Search in 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. 10.1042/bj2580683.Search in Google Scholar PubMed PubMed Central

Knight, D. W., & Little, P. B. (2001). The first efficient method for the intramolecular trapping of benzynes by phenols: a new approach to xanthenes. Journal of the Chemical Society, 14, 1771–1777. 10.1039/b103834f.Search in Google Scholar

Lacerda, V., Jr., dos Santos, D. A., da Silva-Filho, L. C., Greco, S. J., & dos Santos, R. B. (2012). The growing impact of niobium in organic synthesis and catalysis. Aldrichimica Acta, 45, 19–27.Search in Google Scholar

Li, P., Ma, F., Wang, P., & Zhang, Z. H. (2013). Highly efficient low melting mixture catalyzed synthesis of 1, 8-dioxododecahydroxanthene derivatives. Chinese Journal of Chemistry, 31, 757–763. 10.1002/cjoc.201300152.Search in Google Scholar

Limsuwan, S., Trip, E. N., Kouwen, T. R. H. M., Piersma, S., Hiranrat, A., Mahabusarakam, W., Voravuthikunchai, S. P., van Dijl, J. M., & Kayser, O. (2009). Rhodomyrtone: a new candidate as natural antibacterial drug from Rhodomyrtus tomentosa. Phytomedicine, 16, 645–651. 10.1016/j.phymed.2009.01.010.Search in Google Scholar

Locksley, H. D., & Murray, G. (1971). Extractives from Guttiferae. Part X1X. The isolation and structure of two benzophenones, six xanthones and two biflavonoids from the heartwood of Allanblackia floribunda Oliver. Journal of the Chemical Society C: Organic, 1966–1971. 10.1039/j39710001332.Search in Google Scholar

Lü, H. Y., Li, J. J., & Zhang, Z. H. (2009). ZrOCl2–8H2O: a highly efficient catalyst for the synthesis of 1, 8-dioxo-octahydroxanthene derivatives under solvent-free conditions. Applied Organometallic Chemistry, 23, 165–169. 10.1002/aoc.1488.Search in Google Scholar

Makino, M., & Fujimoto, Y. (1999). Flavanones from Baeckea frutescens. Phytochemistry, 50, 273–277. 10.1016/s0031-9422(98)00534-2.Search in Google Scholar

Maleki, B., Gholizadeh, M., & Sepehr, Z. (2011). 1, 3, 5-Trichloro-2, 4, 6-triazinetrion: A versatile heterocycle for the one-pot synthesis of 14-aryl- or alkyl -14H-dibenzo[a, j]xanthene, 1, 8-dioxooctahydroxanthene and 12-aryl-8, 9, 10, 12-tetrahydrobenzo[α]xanthene-11-one derivatives under solventfree conditions. Bulletin of Korean Chemical Society, 32, 1697–1702. 10.5012/bkcs.2011.32.5.1697.Search in Google Scholar

Maleki, B., Barzegar, S., Sepehr, Z., Kermanian, M., & Tayebee, R. (2012). A novel polymeric catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions. Journal of the Iranian Chemical Society, 9, 757–765. 10.1007/s13738-012-0092-5.Search in Google Scholar

Napoleon, A. A., & Khan, F. R. N. (2014). Potential antitubercular and in vitro anti-inflammatory agents: 9-substituted 1, 8-dioxo-octahydroxanthenes through cascade/domino reaction by citric fruit juices. Medicinal Chemistry Research, 23, 4749–4760. 10.1007/s00044-014-1033-x.Search in Google Scholar

Napoleon, A. A., Khan, F. R. N., Jeong, E. D., & Chung, E. H. (2014). Regioselective synthesis of 3, 4, 6, 7-tetrahydro-3, 3-dimethyl-9-phenyl-2H-xanthene-1, 8(5H, 9H)-diones through ascorbic acid catalyzed three-component domino reaction. Tetrahedron Letters, 55, 5656–5659. 10.1016/j.tetlet.2014.08.040.Search in Google Scholar

Nkengfack, A. E., Azebaze, G. A., Vardamides, J. C., Fomum, Z. T., & van Heerden, F. R. (2002). A prenylated xanthone from Allanblackia floribunda. Phytochemistry, 60, 381–384. 10.1016/s0031-9422(02)00036-5.Search in Google Scholar

Ormond, A. B., & Freeman, H. S. (2013). Dye sensitizers for photodynamic therapy. Materials, 6, 817–840. 10.3390/ma6030817.Search in Google Scholar

Oshiro, P. B., Lima, P. S. S. G., Menezes, M. L., & Silva-Filho, L. C. (2015). Synthesis of 4H-chromenes promoted by NbCl5 through multicomponent reaction. Tetrahedron Letters, 56, 4476–4479. 10.1016/j.tetlet.2015.05.099.Search in Google Scholar

Peres, V., & Nagem, T. J. (1997). Trioxygenated naturally occurring xanthones. Phytochemistry, 44, 191–214. 10.1016/s0031-9422(96)00421-9.Search in Google Scholar

Peres, V., Nagem, T. J., & Oliveira, F. F. (2000). Tetraoxygenated naturally occurring xanthones. Phytochemistry, 55, 683–710. 10.1016/s0031-9422(00)00303-4.Search in Google Scholar

Pramanik, A., & Bhar, S. (2012). Alumina-sulfuric acid catalyzed eco-friendly synthesis of xanthenediones. Catalysis Communications, 20, 17–24. 10.1016/j.catcom.2011.12.036.Search in Google Scholar

Preetam, A., Prasad, D. K., Sharma, J., & Nath, M. (2015). Facile one-pot synthesis of oxo-xanthenes under microwave irradiation. Current Microwave Chemistry, 2, 15–23. 10.2174/221333560201150212102647.Search in Google Scholar

Saini, A., Kumar, S., & Sandhu, J. (2006). A new LiBrcatalyzed, facile and efficient method for the synthesis of 14-alkyl or aryl-14H -dibenzo[a, j]xanthenes and tetrahydrobenzo[b]pyrans under solvent-free conventional and microwave heating. Synlett, 2006, 1928–1932. 10.1055/s-2006-947339.Search in Google Scholar

Shirini, F., Mamaghani, M., & Atghia, S. V. (2013). Use of nanoporous Na+-montmorillonite sulfonic acid (SANM) as an eco-benign, efficient and reusable solid acid catalyst for the one-pot synthesis of 14-aryl-14-H-dibenzo[a, j]xanthenes and 1, 8-dioxo-dodecahydroxanthene derivatives. Journal of the Iranian Chemical Society, 10, 415–420. 10.1007/s13738-012-0174-4.Search in Google Scholar

Shirini, F., Abedini, M., Seddighi, M., Jolodar, O. G., Safarpoor, M., Langroodi, N., & Zamani, S. (2014). Introduction of a new bi-SO3H ionic liquid based on 2, 2′-bipyridine as a novel catalyst for the synthesis of various xanthene derivatives. RSC Advances, 4, 63526–63532. 10.1039/c4ra12361a.Search in Google Scholar

Shirini, F., Langarudi, M. S. N., Seddighi, M., & Jolodar, O. G. (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-arylmethylenepyrimidine-2, 4, 6-trione derivatives. Research on Chemical Intermediates, 41, 8483–8497. 10.1007/s11164-014-1905-1.Search in Google Scholar

Sianglum, W., Srimanote, P., Wonglumsom, W., Kittiniyom, K., & Voravuthikunchai, S. P. (2011). Proteome analyses of cellular proteins in methicillin-resistant Staphylococcus aureus treated with rhodomyrtone, a novel antibiotic candidate. PLoS ONE, 6, e16628. 10.1371/journal.pone.0016628.Search in Google Scholar

Soleimani, E., Khodaei, M. M., & Koshvandi, A. T. K. (2011). The efficient synthesis of 14-alkyl or aryl 14Hdibenzo[a, j]xanthenes catalyzed by bismuth(III) chloride under solvent-free conditions. Chinese Chemical Letters, 22, 927–930. 10.1016/j.cclet.2011.01.012.Search in Google Scholar

Urinda, S., Kundu, D., Majee, A., & Hajra, A. (2009). Indium triflate-catalyzed one-pot synthesis of 14-alkyl or aryl-14Hdibenzo[a, j]xanthenes in water. Heteroatom Chemistry, 20, 232–234. 10.1002/hc.20539.Search in Google Scholar

Visutthi, M., Srimanote, P., & Voravuthikunchai, S. P. (2011). Responses in the expression of extracellular proteins in methicillin-resistant Staphylococcus aureus treated with rhodomyrtone. The Microbiological Society of Korea, 49, 956–964. 10.1007/s12275-011-1115-0.Search in Google Scholar

Wang, J. Q., & Harvey, R. G. (2002). Synthesis of polycyclic xanthenes and furans via palladium-catalyzed cyclization of polycyclic aryltriflate esters. Tetrahedron, 58, 5927–5931. 10.1016/s0040-4020(02)00534-3.Search in Google Scholar

Wang, L. M., Sui, Y. Y., & Zhang, L. (2008). Synthesis of 14-{[(un)substituted phenyl] or alkyl}-14H-dibenzo[a, j]xanthenes using Yb(OTf)3 as an efficient catalyst under solvent-free conditions. Chinese Journal of Chemistry, 26, 1105–1108. 10.1002/cjoc.200890196.Search in 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. 10.1016/j.catcom.2008.01.031.Search in Google Scholar

Zhang, Z., & Tao, X. (2008). 2, 4, 6-Trichloro-1, 3, 5-triazinepromoted synthesis of 1, 8-dioxo-octahydroxanthenes under solvent-free conditions. Australian Journal of Chemistry, 61, 77–79. 10.1071/ch07274.Search in Google Scholar

Received: 2016-1-5
Revised: 2016-5-5
Accepted: 2016-5-16
Published Online: 2016-9-28
Published in Print: 2016-12-1

© 2016 Institute of Chemistry, Slovak Academy of Sciences

Downloaded on 27.11.2025 from https://www.degruyterbrill.com/document/doi/10.1515/chempap-2016-0098/html
Scroll to top button