Synthesis of 3,3-Arylidene Bis(4-Hydroxycoumarin) Catalyzed by p-Dodecylbenzenesulfonic Acid (DBSA) in Aqueous Media and Microwave Irradiation
Affiliation(s)
Department of Chemistry, Faculty of Science, Kerman Branch, Islamic Azad University, Kerman, Iran.
Department of Chemistry, Faculty of Science, Kerman Branch, Islamic Azad University, Kerman, Iran.
ABSTRACT
A series of 3,3-arylidene bis(4-hydroxycoumarins) were synthesized by the reaction of aromatic aldehydes with 4-hydroxycoumarin using dodecylbenzenesulfonic acid as Br?nsted acid-surfactant catalyst in aqueous media and under microwave irradiation. The present method is operationally simple and the use of water as the reaction medium makes the process environmentally benign.
A series of 3,3-arylidene bis(4-hydroxycoumarins) were synthesized by the reaction of aromatic aldehydes with 4-hydroxycoumarin using dodecylbenzenesulfonic acid as Br?nsted acid-surfactant catalyst in aqueous media and under microwave irradiation. The present method is operationally simple and the use of water as the reaction medium makes the process environmentally benign.
KEYWORDS
3, 3-Arylidene Bis(4-Hydroxycoumarin), 4-Hydroxycoumarin, Microwave Irradiation, p-Dodecylbenzene-sulfonic Acid (DBSA), Aqueous Media
3, 3-Arylidene Bis(4-Hydroxycoumarin), 4-Hydroxycoumarin, Microwave Irradiation, p-Dodecylbenzene-sulfonic Acid (DBSA), Aqueous Media
Cite this paper
Shamsaddini, A. and Sheikhhosseini, E. (2014) Synthesis of 3,3-Arylidene Bis(4-Hydroxycoumarin) Catalyzed by p-Dodecylbenzenesulfonic Acid (DBSA) in Aqueous Media and Microwave Irradiation. International Journal of Organic Chemistry, 4, 135-141. doi: 10.4236/ijoc.2014.42015.
Shamsaddini, A. and Sheikhhosseini, E. (2014) Synthesis of 3,3-Arylidene Bis(4-Hydroxycoumarin) Catalyzed by p-Dodecylbenzenesulfonic Acid (DBSA) in Aqueous Media and Microwave Irradiation. International Journal of Organic Chemistry, 4, 135-141. doi: 10.4236/ijoc.2014.42015.
References
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http://dx.doi.org/10.1016/S0378-8741(00)00279-8 [5] Laurin, P., Klich, M., Dupis-Hamelin, C., Mauvais, P., Lassaigne, P., Bonnefoy, A. and Musicki, B. (1999) Synthesis and in Vitro Evaluation of Novel Highly Potent Coumarin Inhibitors of Gyrase B. Bioorganic Medical Chemistry Letter, 9, 2079-2084.
http://dx.doi.org/10.1016/S0960-894X(99)00329-7 [6] Donnelly, A.C., Mays, J.R., Burlison, J.A., Nelson, J.T., Vielhauer, G., Holzbeierlein, J. and Blagg, B.S.J. (2008) Synthesis, and Evaluation of Coumarin Ring Derivatives of the Novobiocin Scaffold That Exhibit Antiproliferative Activity. Journal of Organic Chemistry, 73, 8901-8920.
http://dx.doi.org/10.1021/jo801312r [7] Periers, A.-M., Laurin, P., Ferroud, D., Haesslein, J.-L., Klich, M., Dupuis-Hamelin, C., Mauvais, P., Lassaigne, P., Bonnefoy, A. and Musicki, B. (2000) Coumarin Inhibitors of Gyrase B with N-Propargyloxy-Crbamate as an Effective Pyrrole Bioisostere. Bioorganic Medical Chemistry Letter, 10, 161-165.
http://dx.doi.org/10.1016/S0960-894X(99)00654-X [8] Musicki, B., Periers, A.M., Laurin, P., Ferroud, D., Benedetti, Y., Lachaud, S., Chatreaux, F., Haesslein, J.L., IItis, A. and Pierre, C. (2000) Improved Antibacterial Activities of Coumarin Antibiotics Bearing 5’,5’-Dialkylnoviose: Biological Activity of RU79115. Bioorganic Medical Chemistry Letter, 10, 1695-1699.
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http://dx.doi.org/10.1016/S0304-4165(97)00134-7 [11] Moran, S. (2001) The Efficacy of the Flocoumafen Wax Block Bait to Control the Field Rodents Microtus guentheri and Meriones tristrami. Crop Protectio, 20, 529-533.
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http://dx.doi.org/10.1016/j.ejmech.2006.03.007 [14] Manolov, I.I. (1998) Aldehyde Condensation Products of 4-Hydroxycoumarin and Schiff Bases. Tetrahedron Letters, 39, 3041-3042.
http://dx.doi.org/10.1016/S0040-4039(98)00351-7 [15] Kidwai, M., Bansal, V., Mothsra, P., Saxena, S., Somvanshi, R.K., Dey, S. and Singh, T.P. (2007) Molecular Iodine: A Versatile Catalyst for the Synthesis of Bis(4-Hydroxycoumarin) Methanes in Water. Journal of Molecular Catalysis A: Chemical, 268, 76-81.
http://dx.doi.org/10.1016/j.molcata.2006.11.054 [16] Sanghetti, J.N., Kokare, N.D. and Shinde, D.B. (2009) Water Mediated Efficient One-Pot Synthesis of Bis-(4-hy- droxycoumarin)methanes. Green Chemistry Letters and Reviews, 2, 233-235.
http://dx.doi.org/10.1080/17518250903393874 [17] Hagiwara, H., Fujimoto, N., Suzuki, T. and Ando, M. (2000) Synthesis of Methylenebis(4-Hydroxy-2-Pyrone) or Methylenebis(4-Hydroxycoumarin) Derivatives by Organic Solid State Reaction. Heterocycles, 53, 549-552.
http://dx.doi.org/10.3987/COM-99-8817 [18] Elgamal, M.H.A., Shalaby, N.M.M., Shaban, M.A., Duddeck, H., Mikhova, B., Simon, A. and Toth, G. (1997) Synthesis and Spectroscopic Investigation of Some Dimeric Coumarin and Furanocoumarin Models. Monatshefte für Chemie/ Chemical Monthly, 128, 701-712. [19] Hagiwara, H., Miya, S., Suzuki, T., Ando, M., Yamamoto, I. and Kato, M. (1999) Tandem Nucleophilic Reaction Leading to Hydrofurans: Application to One-Pot Synthesis of Antitumor Naphthofuran Natural Product. Heterocycles, 51, 497-500.
http://dx.doi.org/10.3987/COM-98-8430 [20] Sheikhhosseini, E. (2012) Synthesis of 3,3-Arylidene bis(4-hydroxycoumarin) Catalyzed by LiClO4. Trend in Modern Chemistry, 3, 34-37. [21] Li, W., Wang, Y., Wang, Z., Dai, L. and Wang, Y. (2011) Novel SO3H-Functionalized Ionic Liquids Based on Benzimidazolium Cation: Efficient and Recyclable Catalysts for One-Pot Synthesis of Biscoumarin Derivatives. Catalysis Letters, 141, 1651-1658.
http://dx.doi.org/10.1007/s10562-011-0689-9 [22] Mehrabi, H. and Abusaidi, H. (2010) Synthesis of Biscoumarin and 3,4-Dihydropyrano[c]chromene Derivatives Catalysed by Sodium Dodecyl Sulfate (SDS) in Neat Water. Journal of Iranian Chemical Society, 7, 890-894. [23] Khurana, J.M. and Kumar, S. (2009) Tetrabutylammonium Bromide (TBAB): A Neutral and Efficient Catalyst for the Synthesis of Biscoumarin and 3,4-Dihydropyrano[c]chromene Derivatives in Water and Solvent-Free Conditions. Tetrahedron Letters, 50, 4125-4127.
http://dx.doi.org/10.1016/j.tetlet.2009.04.125 [24] Siddiqui, Z. and Farooq, F. (2011) Zn(Proline)2: A Novel Catalyst for the Synthesis of Dicoumarols. Catalysis Science & Technology, 1, 810-816. [25] Khurana, J.M. and Kumar, S. (2010) Ionic Liquid: An Efficient and Recyclable Medium for the Synthesis of Octahy-droquinazolinone and Biscoumarin Derivatives. Monatshefte für Chemie/Chemical Monthly, 141, 561-564. [26] Zhou, J.F., Gong, G.X., An, L.T., Sun, X.J. and Zhu, F.X. (2009) Synthesis of 3,3-Arylidene Bis(4-Hydroxycoumarin) Catalyzed by Sulfamic Acid in Aqueous Media under Microwave Irradiation. Chinese Journal of Organic Chemistry, 29, 1988-1991. [27] Tabatabaeian, K., Heidari, H., Khorshidi, A., Mamaghani, M. and Mahmoodi, N. (2012) Synthesis of Biscoumarin Derivatives by the Reaction of Aldehydes and 4-Hydroxycoumarin Using Ruthenium(III) Chloride Hydrate as a Versatile Homogeneous Catalyst. Journal of the Serbian Chemical Society, 77, 407-413.
http://dx.doi.org/10.2298/JSC110427189T [28] Karimian, R., Piri, F., Safari, A.A. and Davarpanah, S.J. (2013) One-Pot and Chemoselective Synthesis of Bis(4-Hydroxycoumarin) Derivatives Catalyzed by Nano Silica Chloride. Journal of Nanostructure in Chemistry, 3, 52. [29] Sadeghi, B. and Ziya, T. (2013) A Fast, Highly Efficient, and Green Protocol for Synthesis of Biscoumarins Catalyzed by Silica Sulfuric Acid Nanoparticles as a Reusable Catalyst. Journal of Chemistry, 2013, Article ID: 179013. [30] Karmakar, B., Nayak, A. and Banerji, J. (2012) Sulfated Titania Catalyzed Water Mediated Efficient Synthesis of Dicoumarols—A Green Approach. Tetrahedron Letters, 53, 4343-4346. [31] Hamdi, N., Purta, M.C. and Valerga, P. (2008) Synthesis, Structure, Antimicrobial and Antioxidant Investigations of Dicoumarol and Related Compounds. European Journal of Medicinal Chemistry, 43, 2541-2548.
http://dx.doi.org/10.1016/j.ejmech.2008.03.038 [32] Shaterian, H.R. and Honarmand, M. (2009) Uncatalyzed, One-Pot Synthesis of 3,3’-(Benzylene)Bis(4-Hydroxy-2H- Chromen-2-One) Derivatives under Thermal Solvent-Free Conditions. Chinese Journal of Chemistry, 27, 1795-1800.
http://dx.doi.org/10.1002/cjoc.200990302 [33] Al-Kadasi, A.M.A. and Nazeruddin, G.M. (2012) Ultrasound Assisted Catalyst-Free One-Pot Synthesis of Biscoumarins in Neat Water. International Journal of Chemical Sciences, 10, 324-330. [34] Mao, P.C.M., Mouscadet, J.F., Leh, H., Auclair, C. and Hsu, L.Y. (2002) Chemical Modification of Coumarin Dimer and HIV-1 Integrase Inhibitory Activity. Chemical & Pharmaceutical Bulletin, 50, 1634-1637.
http://dx.doi.org/10.1248/cpb.50.1634 [35] Su, C.X., Mouscadet, F., Chiang, C.C., Tsai, H.J. and Hsu, L.Y. (2006) HIV-1 Integrase Inhibition of Biscoumarin Analogues. Chemical & Pharmaceutical Bulletin, 54, 682-686.
http://dx.doi.org/10.1248/cpb.54.682 [36] Manabe, K., Mori, Y. and Kobayashi, S. (2001) Three-Component Carbon-Carbon Bond-Forming Reactions Catalyzed by a Brønsted Acid-Surfactant-Combined Catalyst in Water. Tetrahedron, 57, 2537-2544.
http://dx.doi.org/10.1016/S0040-4020(01)00081-3 [37] Peng, Y.Y., Zhang, Q.L., Yuan, J.J. and Cheng, J.P. (2008) A Facile Aqueous Synthesis of Bis(Indol-3-yl)Alkanes Catalyzed by Dodecylbenzenesulfonic Acid. Chinese Journal of Chemistry, 26, 2228-2232.
http://dx.doi.org/10.1002/cjoc.200890396 [38] Shiri, M. and Zolfigol, M.A. (2009) Surfactant-Type Catalysts in Organic Reactions. Tetrahedron, 65, 587-598.
http://dx.doi.org/10.1016/j.tet.2008.09.085 [39] Han, Y. and Chu, Y. (2005) The Catalytic Properties and Mechanism of Cyclohexane/DBSA/Water Microemulsion System for Esterification. Journal of Molecular Catalysis A: Chemical, 237, 232-237.
http://dx.doi.org/10.1016/j.molcata.2005.04.058 [40] Sheikhhosseini, E., Ghazanfari, D. and Nezamabadi, V. (2013) A New Method for Synthesis of Tetrahydrobenzo[b]-Pyrans and Dihydropyrano[c]Chromenes Using p-Dodecylbenzenesulfonic Acid as Catalyst in Water. Iranian Journal of Catalysis, 3, 197-201. [41] Hashemi, H. and Sardarian, A.R. (2013) 4-Dodecylbenzenesulfonic Acid (DBSA) as an Efficient and Recyclable Catalyst for Synthesis of 14-Aryl- and 14-Alkyl-14-H-Dibenzo[a,j]Xanthenes under Solvent-Free Conditions. Iranian Journal of Science & Technology, A1, 75-82. [42] Bigdeli, M.A., Gholami, G. and Sheikhhosseini, E. (2011) P-Dodecylbenzenesulfonic Acid (DBSA), a Brønsted Acid-Surfactant Catalyst for Biginelli Reaction in Water and under Solvent Free Conditions. Chinese Chemical Letters, 22, 903-906.
http://dx.doi.org/10.1016/j.cclet.2010.12.030
[1] Murray, R.D.H., Mendez, J. and Brown, S.A. (1982) The Natural Coumarins. Wiley, Chichester. [2] Cravotto, G., Nano, G.M., Palmisano, G. and Tagliapietra, S. (2003) The Reactivity of 4-Hhydroxycoumarin under Heterogeneous High-Intensity Sonochemical Conditions. Synthesis, 8, 1286-1292. [3] Jurd, L., Corse, J., King, A.D., Bayne, H. and Mihara, K. (1971) Antimicrobial Properties of Umbelliferone Derivatives. Phytochemistry, 10, 2965-2970.
http://dx.doi.org/10.1016/S0031-9422(00)97333-3 [4] Ojala, T., Remes, S., Haansuu, P., Vuorela, H., Hiltunen, R., Haahtela, K. and Vuorela, P. (2000) Antimicrobial Activity of Some Coumarin Containing Herbal Plants Growing in Finland. Journal of Ethnopharmacology, 73, 299-305.
http://dx.doi.org/10.1016/S0378-8741(00)00279-8 [5] Laurin, P., Klich, M., Dupis-Hamelin, C., Mauvais, P., Lassaigne, P., Bonnefoy, A. and Musicki, B. (1999) Synthesis and in Vitro Evaluation of Novel Highly Potent Coumarin Inhibitors of Gyrase B. Bioorganic Medical Chemistry Letter, 9, 2079-2084.
http://dx.doi.org/10.1016/S0960-894X(99)00329-7 [6] Donnelly, A.C., Mays, J.R., Burlison, J.A., Nelson, J.T., Vielhauer, G., Holzbeierlein, J. and Blagg, B.S.J. (2008) Synthesis, and Evaluation of Coumarin Ring Derivatives of the Novobiocin Scaffold That Exhibit Antiproliferative Activity. Journal of Organic Chemistry, 73, 8901-8920.
http://dx.doi.org/10.1021/jo801312r [7] Periers, A.-M., Laurin, P., Ferroud, D., Haesslein, J.-L., Klich, M., Dupuis-Hamelin, C., Mauvais, P., Lassaigne, P., Bonnefoy, A. and Musicki, B. (2000) Coumarin Inhibitors of Gyrase B with N-Propargyloxy-Crbamate as an Effective Pyrrole Bioisostere. Bioorganic Medical Chemistry Letter, 10, 161-165.
http://dx.doi.org/10.1016/S0960-894X(99)00654-X [8] Musicki, B., Periers, A.M., Laurin, P., Ferroud, D., Benedetti, Y., Lachaud, S., Chatreaux, F., Haesslein, J.L., IItis, A. and Pierre, C. (2000) Improved Antibacterial Activities of Coumarin Antibiotics Bearing 5’,5’-Dialkylnoviose: Biological Activity of RU79115. Bioorganic Medical Chemistry Letter, 10, 1695-1699.
http://dx.doi.org/10.1016/S0960-894X(00)00304-8 [9] Zaneva, O., Manolov, I. and Danchev, N. (2005) Toxicological and Pharmacological Investigations of Newly Synthesized Derivatives of 4-Hydroxycoumarin. Pharmacia (Sofia), 1-2, 85-89. [10] Craciun, A.M., Groenenvan Dooren, M.M.C.L., Thijssen, H.H. and Vermeer, C. (1998) Induction of Prothrombin Synthesis by K-Vitamins Compared in Vitamin K-Dependent and in Brodifacoum-Treated Rats. Biochimica et Biophysica Acta, 1380, 75-81.
http://dx.doi.org/10.1016/S0304-4165(97)00134-7 [11] Moran, S. (2001) The Efficacy of the Flocoumafen Wax Block Bait to Control the Field Rodents Microtus guentheri and Meriones tristrami. Crop Protectio, 20, 529-533.
http://dx.doi.org/10.1016/S0261-2194(01)00016-3 [12] Zavrsnik, D., Muratovic, S., Makuc, D., Plavec, J., Cetina, M., Nagl, A., Clercq, E.D., Balzarini, J. and Mintas, M. (2011) Benzylidene-Bis-(4-Hydroxycoumarin) and Benzopyrano-Coumarin Derivatives: Synthesis, 1H/13C-NMR Conformation and X-Ray Crystal Structure Studies and in Vitro Antiviral Activity Evaluations. Molecules, 16, 6023-6040.
http://dx.doi.org/10.3390/molecules16076023 [13] Ilia, M., Caecilia, M.M. and Nicolay, D. (2006) Synthesis, Structure, Toxicological and Pharmacological Investigations of 4-Hydroxycoumarin Derivatives. European Journal of Medical Chemistry, 41, 882-890.
http://dx.doi.org/10.1016/j.ejmech.2006.03.007 [14] Manolov, I.I. (1998) Aldehyde Condensation Products of 4-Hydroxycoumarin and Schiff Bases. Tetrahedron Letters, 39, 3041-3042.
http://dx.doi.org/10.1016/S0040-4039(98)00351-7 [15] Kidwai, M., Bansal, V., Mothsra, P., Saxena, S., Somvanshi, R.K., Dey, S. and Singh, T.P. (2007) Molecular Iodine: A Versatile Catalyst for the Synthesis of Bis(4-Hydroxycoumarin) Methanes in Water. Journal of Molecular Catalysis A: Chemical, 268, 76-81.
http://dx.doi.org/10.1016/j.molcata.2006.11.054 [16] Sanghetti, J.N., Kokare, N.D. and Shinde, D.B. (2009) Water Mediated Efficient One-Pot Synthesis of Bis-(4-hy- droxycoumarin)methanes. Green Chemistry Letters and Reviews, 2, 233-235.
http://dx.doi.org/10.1080/17518250903393874 [17] Hagiwara, H., Fujimoto, N., Suzuki, T. and Ando, M. (2000) Synthesis of Methylenebis(4-Hydroxy-2-Pyrone) or Methylenebis(4-Hydroxycoumarin) Derivatives by Organic Solid State Reaction. Heterocycles, 53, 549-552.
http://dx.doi.org/10.3987/COM-99-8817 [18] Elgamal, M.H.A., Shalaby, N.M.M., Shaban, M.A., Duddeck, H., Mikhova, B., Simon, A. and Toth, G. (1997) Synthesis and Spectroscopic Investigation of Some Dimeric Coumarin and Furanocoumarin Models. Monatshefte für Chemie/ Chemical Monthly, 128, 701-712. [19] Hagiwara, H., Miya, S., Suzuki, T., Ando, M., Yamamoto, I. and Kato, M. (1999) Tandem Nucleophilic Reaction Leading to Hydrofurans: Application to One-Pot Synthesis of Antitumor Naphthofuran Natural Product. Heterocycles, 51, 497-500.
http://dx.doi.org/10.3987/COM-98-8430 [20] Sheikhhosseini, E. (2012) Synthesis of 3,3-Arylidene bis(4-hydroxycoumarin) Catalyzed by LiClO4. Trend in Modern Chemistry, 3, 34-37. [21] Li, W., Wang, Y., Wang, Z., Dai, L. and Wang, Y. (2011) Novel SO3H-Functionalized Ionic Liquids Based on Benzimidazolium Cation: Efficient and Recyclable Catalysts for One-Pot Synthesis of Biscoumarin Derivatives. Catalysis Letters, 141, 1651-1658.
http://dx.doi.org/10.1007/s10562-011-0689-9 [22] Mehrabi, H. and Abusaidi, H. (2010) Synthesis of Biscoumarin and 3,4-Dihydropyrano[c]chromene Derivatives Catalysed by Sodium Dodecyl Sulfate (SDS) in Neat Water. Journal of Iranian Chemical Society, 7, 890-894. [23] Khurana, J.M. and Kumar, S. (2009) Tetrabutylammonium Bromide (TBAB): A Neutral and Efficient Catalyst for the Synthesis of Biscoumarin and 3,4-Dihydropyrano[c]chromene Derivatives in Water and Solvent-Free Conditions. Tetrahedron Letters, 50, 4125-4127.
http://dx.doi.org/10.1016/j.tetlet.2009.04.125 [24] Siddiqui, Z. and Farooq, F. (2011) Zn(Proline)2: A Novel Catalyst for the Synthesis of Dicoumarols. Catalysis Science & Technology, 1, 810-816. [25] Khurana, J.M. and Kumar, S. (2010) Ionic Liquid: An Efficient and Recyclable Medium for the Synthesis of Octahy-droquinazolinone and Biscoumarin Derivatives. Monatshefte für Chemie/Chemical Monthly, 141, 561-564. [26] Zhou, J.F., Gong, G.X., An, L.T., Sun, X.J. and Zhu, F.X. (2009) Synthesis of 3,3-Arylidene Bis(4-Hydroxycoumarin) Catalyzed by Sulfamic Acid in Aqueous Media under Microwave Irradiation. Chinese Journal of Organic Chemistry, 29, 1988-1991. [27] Tabatabaeian, K., Heidari, H., Khorshidi, A., Mamaghani, M. and Mahmoodi, N. (2012) Synthesis of Biscoumarin Derivatives by the Reaction of Aldehydes and 4-Hydroxycoumarin Using Ruthenium(III) Chloride Hydrate as a Versatile Homogeneous Catalyst. Journal of the Serbian Chemical Society, 77, 407-413.
http://dx.doi.org/10.2298/JSC110427189T [28] Karimian, R., Piri, F., Safari, A.A. and Davarpanah, S.J. (2013) One-Pot and Chemoselective Synthesis of Bis(4-Hydroxycoumarin) Derivatives Catalyzed by Nano Silica Chloride. Journal of Nanostructure in Chemistry, 3, 52. [29] Sadeghi, B. and Ziya, T. (2013) A Fast, Highly Efficient, and Green Protocol for Synthesis of Biscoumarins Catalyzed by Silica Sulfuric Acid Nanoparticles as a Reusable Catalyst. Journal of Chemistry, 2013, Article ID: 179013. [30] Karmakar, B., Nayak, A. and Banerji, J. (2012) Sulfated Titania Catalyzed Water Mediated Efficient Synthesis of Dicoumarols—A Green Approach. Tetrahedron Letters, 53, 4343-4346. [31] Hamdi, N., Purta, M.C. and Valerga, P. (2008) Synthesis, Structure, Antimicrobial and Antioxidant Investigations of Dicoumarol and Related Compounds. European Journal of Medicinal Chemistry, 43, 2541-2548.
http://dx.doi.org/10.1016/j.ejmech.2008.03.038 [32] Shaterian, H.R. and Honarmand, M. (2009) Uncatalyzed, One-Pot Synthesis of 3,3’-(Benzylene)Bis(4-Hydroxy-2H- Chromen-2-One) Derivatives under Thermal Solvent-Free Conditions. Chinese Journal of Chemistry, 27, 1795-1800.
http://dx.doi.org/10.1002/cjoc.200990302 [33] Al-Kadasi, A.M.A. and Nazeruddin, G.M. (2012) Ultrasound Assisted Catalyst-Free One-Pot Synthesis of Biscoumarins in Neat Water. International Journal of Chemical Sciences, 10, 324-330. [34] Mao, P.C.M., Mouscadet, J.F., Leh, H., Auclair, C. and Hsu, L.Y. (2002) Chemical Modification of Coumarin Dimer and HIV-1 Integrase Inhibitory Activity. Chemical & Pharmaceutical Bulletin, 50, 1634-1637.
http://dx.doi.org/10.1248/cpb.50.1634 [35] Su, C.X., Mouscadet, F., Chiang, C.C., Tsai, H.J. and Hsu, L.Y. (2006) HIV-1 Integrase Inhibition of Biscoumarin Analogues. Chemical & Pharmaceutical Bulletin, 54, 682-686.
http://dx.doi.org/10.1248/cpb.54.682 [36] Manabe, K., Mori, Y. and Kobayashi, S. (2001) Three-Component Carbon-Carbon Bond-Forming Reactions Catalyzed by a Brønsted Acid-Surfactant-Combined Catalyst in Water. Tetrahedron, 57, 2537-2544.
http://dx.doi.org/10.1016/S0040-4020(01)00081-3 [37] Peng, Y.Y., Zhang, Q.L., Yuan, J.J. and Cheng, J.P. (2008) A Facile Aqueous Synthesis of Bis(Indol-3-yl)Alkanes Catalyzed by Dodecylbenzenesulfonic Acid. Chinese Journal of Chemistry, 26, 2228-2232.
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http://dx.doi.org/10.1016/j.tet.2008.09.085 [39] Han, Y. and Chu, Y. (2005) The Catalytic Properties and Mechanism of Cyclohexane/DBSA/Water Microemulsion System for Esterification. Journal of Molecular Catalysis A: Chemical, 237, 232-237.
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