A new and efficient method for the synthesis of dicoumarol (3,3'-methylene-bis-4-hydroxycoumarin) in the presence of catalytic amounts of silica-supported Preyssler nanoparticles (SPN) is reported. The catalyst performs very well in comparison with other heteropolyacids catalysts. An important advantage of this catalyst is the ease of separating it from the reaction mixture, as well as the fact that it could be recycled a number of times.
Published in | American Journal of Heterocyclic Chemistry (Volume 1, Issue 2) |
DOI | 10.11648/j.ajhc.20150102.11 |
Page(s) | 21-28 |
Creative Commons |
This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited. |
Copyright |
Copyright © The Author(s), 2015. Published by Science Publishing Group |
Dicoumarol, Silica-Supported Preyssler, Nanoparticles, Recyclable, Catalyst, Heteropolyacids
[1] | (a) D. Zavrsnik, S. Muratovic, S. Spirtovic, D. Softic, M. Medic-Saric, Bosnian J. Basic Med. Sci. 2008, 8, 277. (b) D. Zavrsnik, S. Muratovic, D. Makuc, J. Plavec, M. Cetina, A. Nagl, E. D. Clercq, J. Balzarini, M. Mintas, Molecules. 2011, 16, 6023. |
[2] | (a) S. Qadir, A.A. Dar, K.Z. Khan, Synth. Commun. 2008, 38, 3490. (b) J. F. Zhou, G. X. Gong, L. T. An, X. J. Sun, F. X. Zhu, Chin. J. Org. Chem. 2009, 29, 1988. (c) J. M. Khurana, S. Kumar, Tetrahedron Lett. 2009, 50, 4125. |
[3] | A. M. A. AL-Kadasi, G. M. Nazeruddin, Int. J. Chem. Sci. 2012, 10, 324. |
[4] | M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R. K. Somavanshi, S. Dey, T. P. Singh, J. Mol. Catal. A: Chem. 2007, 268, 76. |
[5] | K. M. Khan, S. Iqbal, M. A. Lodhi, G. M. Maharvi, Z. Ullah, M. I. Choudhary, A. Rahman, S. Perveen, Bioorg. Med. Chem. 2004, 12, 1963. |
[6] | H. Hagiwara, N. Fujimoto, T. Suzuki, M. Ando, Heterocycles. 2000, 53, 549. |
[7] | A. Shamsaddini, E. Sheikhhosseini, Int. J. Org. Chem. 2014, 4, 135. |
[8] | E. Sheikhhosseini, Trend. Mod. Chem. 2012, 3, 34. |
[9] | H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 2010, 7, 890. |
[10] | Z. Siddiqui, F. Farooq, Catal. Sci. Technol. 2011, 1, 810. |
[11] | J. M. Khurana, S. Kumar, Tetrahedron. Lett. 2009, 50, 4125. |
[12] | (a) J. M. Khurana, S. Kumar, Monatsh. Chem. 2010, 141, 561. (b) A. Tzani, A. Douka, A. Papadopoulos, E. A. Pavlatou, E. Voutsas, A. Detsi, ACS Sustainable Chem. Eng. 2013, 1, 1180. |
[13] | (a) J. M. Khurana, K. Vij, J. Chem. Sci. 2012, 124, 907. (b) H. Babaei, N. Montazeri, Orient. J. Chem. 2014, 30, 577. |
[14] | G. Appendino, G. Cravotto, S. Tagliapietra, S. Ferraro, G. M. Nano, G. Palmisano, Helv. Chim. Acta. 1991, 51. |
[15] | I. Manolov, C. M. Moessmer, N. D. Danchev, Eur. J. Med. Chem. 2006, 41, 882. |
[16] | R. D. H. Murray, J. Mendez, S. A. Brown, The Natural Coumarins: Ocurrence, Chemistry and Biochemistry, John Wiley & Sons Ltd, Chichester, New York, 1982. |
[17] | J. Lehmann, Lancet. 1943, 241, 611. |
[18] | W. R. Sullivan, C. F. Huebner, M. A. Stahmann, K. P. Link, J. Am. Soc. 1943, 65, 2288. |
[19] | K. M. Khan, S. Iqbal, M. A. Lodhi, G. M. Mahaveri, Z. Ullah, M. I. Choudhary, A. U. Rahman, S. Perveen, Bioorg. Med. Chem. 2004, 12, 1963. |
[20] | R. S. Overmann, M. A. Stahmann, C. F. Huebner, W. R. Sullivan, L. Spero, D. G. Doherty, M. Ikawa, L. Graf, S. Roseman, K. P. Link, J. Biol. Chem. 1944, 153, 5. |
[21] | I. Kostava, I. Manolov, I. Nicolova, S. Konstantonov, M. Karaivanova, Eur. J. Med. Chem. 2001, 36, 339. |
[22] | E. Adami, E. M. Uberti, C. Turba, Archivio Italiano di Scienze Farmacologiche. 1959, 9, 61. |
[23] | Z. H. Chohan, A. U. Shaikh, A. Rauf, C. T. Supuran, J. Enz. Inh. Med. Chem. 2006, 21, 741. |
[24] | N. Hamdi, M. C. Puerta, P. Valerga, Eur. J. Med. Chem. 2008, 43, 2541. |
[25] | A. C. Luchini, P. Rodrigues-Orsi, S. H. Cestari, Biol. Pharma Bull. 2008, 31, 1343. |
[26] | D. H. Mahajan, C. Pannecouque, E. de Clercq, K. H. Chikhalia, Archiv der Pharmazie. 2009, 342, 281. |
[27] | P. Stern, M. Dezelic, R. Kosak, Naunyn-Schmiedebergs Archiv f¨ur Experimentelle Pathologie und Pharmakologie. 1957, 232, 356. |
[28] | M. A. Velasco-Vel´azquez, J. Agramonte-Hevia, D. Barrera, Cancer Lett. 2003, 198, 179. |
[29] | A. Goth, Science. 1945, 101, 382. |
[30] | V. Dad´ak, K. Hod’´ak, Experientia. 1966, 22, 38. |
[31] | T. Cresteil, A. K. Jaiswal, Biochem. Pharm. 1991, 42, 1021. |
[32] | G. Asher, O. Dym, P. Tsvetkov, J. Adler, Y. Shaul, Biochemistry. 2006, 45, 6372. |
[33] | E. Johansson, G. N. Parkinson, W. A. Denny, S. Neidle, J. Med. Chem. 2003, 46, 4009. |
[34] | K. Ito, M. Nakanishi, W.-C. Lee, J. Biol. Chem. 2008, 283, 13889. |
[35] | T. Okuhara, N. Mizuno, M. Misono, Advances in Catalysis. Catalytic Chemistry of Heteropoly compounds. 1996, 41, 113. |
[36] | I. V. Kozhevnikov, Russ. Chem. Rev. 1987, 56, 811. |
[37] | Y. Izumi, K. Urabe, M. Onaka, Zeolite, Clay and Heteropoly Acid in Organic Reactions, Kodansha/VCH, Tokyo, 1992. |
[38] | I. V. Kozhevnikov, Chem. Rev. 1998, 98, 171. |
[39] | I. V. Kozhevnikov, Catalysts for fine chemicals, in: Catalysis by Polyoxometalates, vol. 2, Wiley, Chichester, 2002. |
[40] | J. B. Moffat, Metal-Oxygen Clusters: The Surface and Catalytic Properties of Heteropoly Oxometalates, Kluwer, New York, 2001. |
[41] | I. V. Kozhevnikov, Appl Catalysis A: General. 2003, 256, 3. |
[42] | F. F. Bamoharram, M. M. Heravi, M. Roshani, M. Jahangir, A. Gharib, J. Mol. Catal. 2007, 271, 126. |
[43] | F. F. Bamoharram, M. M. Heravi, M. Roshani, A. Gharib, M. Jahangir, J. Mol. Catalysis A: Chemical. 2006, 252, 90. |
[44] | F. F. Bamoharram, M. M. Heravi, M. Roshani, M. Jahangir, A. Gharib, J. Appl. Catalysis A: General. 2006, 302, 42. |
[45] | F. F. Bamoharram, M. M. Heravi, M. Roshani, A. Gharib, M. Jahangir, J. Chinese Chem Soc. 2007, 54, 1017. |
[46] | A. Gharib, J. W. Scheeren3, F. F. Bamoharram, M. Roshani, M. Jahangir, Polish J. Chem Tech. 2009, 11, 30. |
[47] | A. Gharib, M. Jahangir, M. Roshani, J. W. Scheeren, Bulgarian Chem Commun. 2010, 42, 210. |
[48] | A. Gharib, M. Jahangir, M. Roshani, J. W. Scheeren, Synth Commun. 2012, 42, 3311. |
[49] | a) A. Gharib, B. R. Hashemipour Khorasani, M. Jahangir, M. Roshani, L. Bakhtiari, S. Mohadeszadeh, Bulgarian Chem Commun. 2014, 46, 165. b) A. Gharib, N. Noroozi Pesyan, L. Vojdani Fard, M. Roshani, Hindawi Publishing Corporation, Organic Chemistry International, Volume 2014, Article ID 906801, 6 pages. |
[50] | a) A. Gharib, N. Noroozi Pesyan, M. Jahangir, M. Roshani, J. W. Scheeren, L Bakhtiari, S. Mohadeszadeh, S. Lagzian, S. Ahmadi, Bulgarian Chem Commun. 2014, 46, 215. b) M. M. Heravi, S. Sadjadi, S. Sadjadi, H. A. Oskooie, R. H. Shoar, and F. F. Bamoharram, South African Journal of Chemistry. 2009, 62, 2009. |
[51] | G. A. Tsigdinos, C. J. Hallada, Inorg. Chem. 1968, 7, 437. |
[52] | Y. Mahha, A. Atlamsani, J. C. Blais, M. Tessier, J. M. Brégeault, L. Salles, J. Mol. Catal. A: Chemical. 2005, 234, 63. |
[53] | M. M. Heravi, K. Bakhtiari, T. Benmorad, F. F. Bamoharram, M. M. Heravi, H. A. Oskooie, H. M. Tehrani, Monatshefte für Chemie. 2007, 138, 449. |
[54] | S. Qadir, A. A. Dar, K. Z. Khan, Synth. Commun. 2008, 38, 3490. |
[55] | M. Kidwai, V. Bansal, P. Mothsra, S. Saxena, R. K. Somavanshi, S. Dey, T. P. Singh, J. Mol. Catal. A: Chem. 2007, 268, 76. |
[56] | M. T. Pope, Heteropoly and Isopoly Oxometalates, Springer, Berlin, 1983. |
[57] | M. H. Alizadeh, S. P. Harmalker, Y. Jeannin, J. Martin-Frere, M. T. Pope, J. Am. Chem. Soc. 1985, 107, 2662. |
[58] | W. Shanshan, Z. Weihong, W. Jum, R. Xiaoqian, Catal. Lett. 2008, 123, 276. |
APA Style
Ali Gharib, Nader Noroozi Pesyan, Leila Vojdani Fard, Mina Roshani. (2015). Catalytical Synthesis of Dicoumarols Using Silica-Supported Preyssler Nanoparticles (SPN), H14[NaP5W30O110]/SiO2. American Journal of Heterocyclic Chemistry, 1(2), 21-28. https://doi.org/10.11648/j.ajhc.20150102.11
ACS Style
Ali Gharib; Nader Noroozi Pesyan; Leila Vojdani Fard; Mina Roshani. Catalytical Synthesis of Dicoumarols Using Silica-Supported Preyssler Nanoparticles (SPN), H14[NaP5W30O110]/SiO2. Am. J. Heterocycl. Chem. 2015, 1(2), 21-28. doi: 10.11648/j.ajhc.20150102.11
@article{10.11648/j.ajhc.20150102.11, author = {Ali Gharib and Nader Noroozi Pesyan and Leila Vojdani Fard and Mina Roshani}, title = {Catalytical Synthesis of Dicoumarols Using Silica-Supported Preyssler Nanoparticles (SPN), H14[NaP5W30O110]/SiO2}, journal = {American Journal of Heterocyclic Chemistry}, volume = {1}, number = {2}, pages = {21-28}, doi = {10.11648/j.ajhc.20150102.11}, url = {https://doi.org/10.11648/j.ajhc.20150102.11}, eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20150102.11}, abstract = {A new and efficient method for the synthesis of dicoumarol (3,3'-methylene-bis-4-hydroxycoumarin) in the presence of catalytic amounts of silica-supported Preyssler nanoparticles (SPN) is reported. The catalyst performs very well in comparison with other heteropolyacids catalysts. An important advantage of this catalyst is the ease of separating it from the reaction mixture, as well as the fact that it could be recycled a number of times.}, year = {2015} }
TY - JOUR T1 - Catalytical Synthesis of Dicoumarols Using Silica-Supported Preyssler Nanoparticles (SPN), H14[NaP5W30O110]/SiO2 AU - Ali Gharib AU - Nader Noroozi Pesyan AU - Leila Vojdani Fard AU - Mina Roshani Y1 - 2015/05/30 PY - 2015 N1 - https://doi.org/10.11648/j.ajhc.20150102.11 DO - 10.11648/j.ajhc.20150102.11 T2 - American Journal of Heterocyclic Chemistry JF - American Journal of Heterocyclic Chemistry JO - American Journal of Heterocyclic Chemistry SP - 21 EP - 28 PB - Science Publishing Group SN - 2575-5722 UR - https://doi.org/10.11648/j.ajhc.20150102.11 AB - A new and efficient method for the synthesis of dicoumarol (3,3'-methylene-bis-4-hydroxycoumarin) in the presence of catalytic amounts of silica-supported Preyssler nanoparticles (SPN) is reported. The catalyst performs very well in comparison with other heteropolyacids catalysts. An important advantage of this catalyst is the ease of separating it from the reaction mixture, as well as the fact that it could be recycled a number of times. VL - 1 IS - 2 ER -