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
English
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
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[1] P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, UK, 1998.[1] P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, Oxford, UK, 1998.
-
[2] M. Poliakoff, M.J. Fitzpatric, T.R. Farren, P.T. Anastas, Green chemistry: science and politics of change, Science 297 (2002) 807-810.[2] M. Poliakoff, M.J. Fitzpatric, T.R. Farren, P.T. Anastas, Green chemistry: science and politics of change, Science 297 (2002) 807-810.
-
[3] I.T. Horváth, P.T. Anastas, Innovations and green chemistry, Chem. Rev. 107 (2007) 2169-2173.[3] I.T. Horváth, P.T. Anastas, Innovations and green chemistry, Chem. Rev. 107 (2007) 2169-2173.
-
[4] T. Welton, Room-temperature ionic liquids. Solvents for synthesis and catalysis, Chem. Rev. 99 (1999) 2071-2084.[4] T. Welton, Room-temperature ionic liquids. Solvents for synthesis and catalysis, Chem. Rev. 99 (1999) 2071-2084.
-
[5] T. Welton, Ionic liquids in catalysis, Coord. Chem. Rev. 248 (2004) 2459- 2477.[5] T. Welton, Ionic liquids in catalysis, Coord. Chem. Rev. 248 (2004) 2459- 2477.
-
[6] P. Wasserscheid, W. Keim, Ionic liquids-new "solutions" for transition metal catalysis, Angew. Chem. Int. Ed. 39 (2000) 3772-3789.[6] P. Wasserscheid, W. Keim, Ionic liquids-new "solutions" for transition metal catalysis, Angew. Chem. Int. Ed. 39 (2000) 3772-3789.
-
[7] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, 3-Methyl-1-sulfonic acid imidazolium chloride as a new, efficient and recyclable catalyst and solvent for the preparation of N-sulfonyl imines at room temperature, J. Iran. Chem. Soc. 7 (2010) 646-651.[7] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, 3-Methyl-1-sulfonic acid imidazolium chloride as a new, efficient and recyclable catalyst and solvent for the preparation of N-sulfonyl imines at room temperature, J. Iran. Chem. Soc. 7 (2010) 646-651.
-
[8] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Ionic liquid 3-methyl-1- sulfonic acid imidazolium chloride as a novel and highly efficient catalyst for the very rapid synthesis of bis(indolyl)methanes under solvent-free conditions, Org. Prep. Proced. Int. 42 (2010) 95-102.[8] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, Ionic liquid 3-methyl-1- sulfonic acid imidazolium chloride as a novel and highly efficient catalyst for the very rapid synthesis of bis(indolyl)methanes under solvent-free conditions, Org. Prep. Proced. Int. 42 (2010) 95-102.
-
[9] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, An efficient method for the nitration of phenols with nano2 in the presence of 3-methyl-1-sulfonic acid imidazolium, Sci. Iran. Trans. C: Chem. Chem. Eng. 17 (2010) 31-36.[9] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, A. Zare, An efficient method for the nitration of phenols with nano2 in the presence of 3-methyl-1-sulfonic acid imidazolium, Sci. Iran. Trans. C: Chem. Chem. Eng. 17 (2010) 31-36.
-
[10] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Rapid synthesis of 1-amidoalkyl-2-naphthols over sulfonic acid functionalized imidazolium salts, Appl. Catal. A: Gen. 400 (2011) 70-81.[10] M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, V. Khakyzadeh, Rapid synthesis of 1-amidoalkyl-2-naphthols over sulfonic acid functionalized imidazolium salts, Appl. Catal. A: Gen. 400 (2011) 70-81.
-
[11] S.L. Schreiber, Target-oriented and diversity-oriented organic synthesis in drug discovery, Science 287 (2000) 1964-1969.[11] S.L. Schreiber, Target-oriented and diversity-oriented organic synthesis in drug discovery, Science 287 (2000) 1964-1969.
-
[12] A. Domling, Recent advances in isocyanide-based multicomponent chemistry, Curr. Opin. Chem. Biol. 6 (2002) 306-313.[12] A. Domling, Recent advances in isocyanide-based multicomponent chemistry, Curr. Opin. Chem. Biol. 6 (2002) 306-313.
-
[13] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, Germany, 2005.[13] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, Germany, 2005.
-
[14] V. Polshettiwar, R.S. Varma, Greener and expeditious synthesis of bioactive heterocycles using microwave irradiation, Pure. Appl. Chem. 80 (2008) 777-790.[14] V. Polshettiwar, R.S. Varma, Greener and expeditious synthesis of bioactive heterocycles using microwave irradiation, Pure. Appl. Chem. 80 (2008) 777-790.
-
[15] A. Hasaninejad, A. Zare, M. Shekouhy, Highly efficient synthesis of triazolo[1, 2- a]indazole-triones and novel spiro triazolo[1,2-a]indazole-tetraones under solvent- free conditions, Tetrahedron 67 (2011) 390-400.[15] A. Hasaninejad, A. Zare, M. Shekouhy, Highly efficient synthesis of triazolo[1, 2- a]indazole-triones and novel spiro triazolo[1,2-a]indazole-tetraones under solvent- free conditions, Tetrahedron 67 (2011) 390-400.
-
[16] S. Stavber, Recent advances in the application of selectfluorTM F-TEDA-BF4 as a versatile mediator or catalyst in organic synthesis, Molecules 16 (2011) 6432- 6464.[16] S. Stavber, Recent advances in the application of selectfluorTM F-TEDA-BF4 as a versatile mediator or catalyst in organic synthesis, Molecules 16 (2011) 6432- 6464.
-
[17] J.P. Poupelin, G. Saint-Ruf, O. Foussard-Blanpin, et al., H4SiW12O40 catalyzed onepot synthesis of 12-aryl-8, 9,10,12-tetrahydrobenzo[a] xanthen-11-ones under solvent-free conditions, Eur. J. Med. Chem. 13 (1978) 67-71.[17] J.P. Poupelin, G. Saint-Ruf, O. Foussard-Blanpin, et al., H4SiW12O40 catalyzed onepot synthesis of 12-aryl-8, 9,10,12-tetrahydrobenzo[a] xanthen-11-ones under solvent-free conditions, Eur. J. Med. Chem. 13 (1978) 67-71.
-
[18] J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison, C. Tsai, Potentiation of the antiviral activity of poly r(A-U) by xanthene dyes, Cell. Biol. Int. Rep. 14 (1990) 1075-1084.[18] J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison, C. Tsai, Potentiation of the antiviral activity of poly r(A-U) by xanthene dyes, Cell. Biol. Int. Rep. 14 (1990) 1075-1084.
-
[19] G.W. Rewcastle, G.J. Atwell, L. Zhuang, B.C. Baguley, W.A. Denny, Potential antitumor agents. 61. Structure-activity relationships for in vivo colon 38 activity among disubstituted 9-oxo-9H-xanthene-4-acetic acids, J. Med. Chem. 34 (1991) 217-222.[19] G.W. Rewcastle, G.J. Atwell, L. Zhuang, B.C. Baguley, W.A. Denny, Potential antitumor agents. 61. Structure-activity relationships for in vivo colon 38 activity among disubstituted 9-oxo-9H-xanthene-4-acetic acids, J. Med. Chem. 34 (1991) 217-222.
-
[20] A.T. Peters, M.J. Bide, Amino derivatives of 1,8-naphthalic anhydride and derived dyes for synthetic-polymer fibres, Dyes Pigm. 6 (1985) 349-375.[20] A.T. Peters, M.J. Bide, Amino derivatives of 1,8-naphthalic anhydride and derived dyes for synthetic-polymer fibres, Dyes Pigm. 6 (1985) 349-375.
-
[21] C.G. Knight, T. Stephens, Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles, Biochem. J. 258 (1989) 683-687.[21] C.G. Knight, T. Stephens, Xanthene-dye-labelled phosphatidylethanolamines as probes of interfacial pH. Studies in phospholipid vesicles, Biochem. J. 258 (1989) 683-687.
-
[22] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.[22] M. Ahmad, T.A. King, D.K. Ko, B.H. Cha, J. Lee, Performance and photostability of xanthene and pyrromethene laser dyes in sol-gel phases, J. Phys. D: Appl. Phys. 35 (2002) 1473-1476.
-
[23] A. Bekaert, J. Andrieux, M. Plat, New total synthesis of bikaverin, Tetrahedron Lett. 33 (1992) 2805-2806.[23] A. Bekaert, J. Andrieux, M. Plat, New total synthesis of bikaverin, Tetrahedron Lett. 33 (1992) 2805-2806.
-
[24] D.W. Knight, P.B. Little, The first efficient method for the intramolecular trapping of benzynes by phenols: a new approach to xanthenes, J. Chem. Soc. Perkin Trans. 1 15 (2001) 1771-1777.[24] D.W. Knight, P.B. Little, The first efficient method for the intramolecular trapping of benzynes by phenols: a new approach to xanthenes, J. Chem. Soc. Perkin Trans. 1 15 (2001) 1771-1777.
-
[25] C.W. Kuo, J.M. Fang, Synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl-carbonyl coupling reactions, Synth. Commun. 31 (2001) 877-892.[25] C.W. Kuo, J.M. Fang, Synthesis of xanthenes, indanes, and tetrahydronaphthalenes via intramolecular phenyl-carbonyl coupling reactions, Synth. Commun. 31 (2001) 877-892.
-
[26] J.Q. Wang, R.G. Harvey, Synthesis of polycyclic xanthenes and furans via palladium- catalyzed cyclization of polycyclic aryltriflate esters, Tetrahedron 58 (2002) 5927-5931.[26] J.Q. Wang, R.G. Harvey, Synthesis of polycyclic xanthenes and furans via palladium- catalyzed cyclization of polycyclic aryltriflate esters, Tetrahedron 58 (2002) 5927-5931.
-
[27] H.R. Shaterian, A. Hosseinian, M. Ghashang, Ferric hydrogen sulfate as an efficient heterogeneous catalyst for environmentally friendly greener synthesis of 1,8- dioxo-octahydroxanthenes, Turk. J. Chem. 33 (2009) 233-240.[27] H.R. Shaterian, A. Hosseinian, M. Ghashang, Ferric hydrogen sulfate as an efficient heterogeneous catalyst for environmentally friendly greener synthesis of 1,8- dioxo-octahydroxanthenes, Turk. J. Chem. 33 (2009) 233-240.
-
[28] J. Li, L. Lu, W. Su, A new strategy for the synthesis of benzoxanthenes catalyzed by proline triflate in water, Tetrahedron Lett. 51 (2010) 2434-2437.[28] J. Li, L. Lu, W. Su, A new strategy for the synthesis of benzoxanthenes catalyzed by proline triflate in water, Tetrahedron Lett. 51 (2010) 2434-2437.
-
[29] B. Das, K. Laxminarayana, M. Krishnaiah, Y. Srinivas, An efficient and convenient protocol for the synthesis of novel 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives, Synlett (2007) 3107-3112.[29] B. Das, K. Laxminarayana, M. Krishnaiah, Y. Srinivas, An efficient and convenient protocol for the synthesis of novel 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one derivatives, Synlett (2007) 3107-3112.
-
[30] J. Li, W. Tang, L. Lu, W. Su, Strontium triflate catalyzed one-pot condensation of bnaphthol, aldehydes and cyclic 1,3-dicarbonyl compounds, Tetrahedron Lett. 49 (2008) 7117-7120.[30] J. Li, W. Tang, L. Lu, W. Su, Strontium triflate catalyzed one-pot condensation of bnaphthol, aldehydes and cyclic 1,3-dicarbonyl compounds, Tetrahedron Lett. 49 (2008) 7117-7120.
-
[31] N. Foroughifar, A. Mobinikhaledi, H. Moghanian, A catalytic and green procedure for synthesis of 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11- one derivatives under solvent-free conditions, Int. J. Green Nanotechnol. Phys. Chem. 1 (2009) 57-63.[31] N. Foroughifar, A. Mobinikhaledi, H. Moghanian, A catalytic and green procedure for synthesis of 12-aryl- or 12-alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11- one derivatives under solvent-free conditions, Int. J. Green Nanotechnol. Phys. Chem. 1 (2009) 57-63.
-
[32] K. Tabatabaeian, A. Khorshidi, M. Mamaghani, A. Dadashi, M.K. Jalali, One-pot synthesis of tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by ruthenium chloride hydrate as a homogeneous catalyst, Can. J. Chem. 89 (2011) 623-627.[32] K. Tabatabaeian, A. Khorshidi, M. Mamaghani, A. Dadashi, M.K. Jalali, One-pot synthesis of tetrahydrobenzo[a]xanthen-11-one derivatives catalyzed by ruthenium chloride hydrate as a homogeneous catalyst, Can. J. Chem. 89 (2011) 623-627.
-
[33] A. Zarei, A.R. Hajipour, L. Khazdooz, The one-pot synthesis of 14-aryl or alkyl-14Hdibenzo[a,j] xanthenes catalyzed by P2O5/Al2O3 under microwave irradiation, Dyes Pigm. 85 (2010) 133-138.[33] A. Zarei, A.R. Hajipour, L. Khazdooz, The one-pot synthesis of 14-aryl or alkyl-14Hdibenzo[a,j] xanthenes catalyzed by P2O5/Al2O3 under microwave irradiation, Dyes Pigm. 85 (2010) 133-138.
-
[34] B.B. Mirjalili, A. Bamoniri, A. Akbari, BF3·SiO2: an efficient alternative for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes, Tetrahedron Lett. 49 (2008) 6454-6456.[34] B.B. Mirjalili, A. Bamoniri, A. Akbari, BF3·SiO2: an efficient alternative for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]xanthenes, Tetrahedron Lett. 49 (2008) 6454-6456.
-
[35] N.D. Kokare, J.N. Sangshetti, D.B. Shinde, Oxalic acid as a catalyst for efficient synthesis of bis-(indolyl)methanes, and 14-aryl-14H-dibenzo[a,j]xanthenes in water, Chin. Chem. Lett. 19 (2008) 1186-1189.[35] N.D. Kokare, J.N. Sangshetti, D.B. Shinde, Oxalic acid as a catalyst for efficient synthesis of bis-(indolyl)methanes, and 14-aryl-14H-dibenzo[a,j]xanthenes in water, Chin. Chem. Lett. 19 (2008) 1186-1189.
-
[36] F. Shirini, N.G. Khaligh, G.H. Imanzadeh, P.G. Ghasem-Abadi, 1,3-Dibromo-5,5- dimethylhydantoin (DBH)/kaolin: an efficient reagent system for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions, Chin. Chem. Lett. 23 (2012) 1145-1148.[36] F. Shirini, N.G. Khaligh, G.H. Imanzadeh, P.G. Ghasem-Abadi, 1,3-Dibromo-5,5- dimethylhydantoin (DBH)/kaolin: an efficient reagent system for the synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes under solvent-free conditions, Chin. Chem. Lett. 23 (2012) 1145-1148.
-
[37] J. Safaei-Ghomi, M.A. Ghasemzadeh, Zinc oxide nanoparticles: a highly efficient and readily recyclable catalyst for the synthesis of xanthenes, Chin. Chem. Lett. 23 (2012) 1225-1229.[37] J. Safaei-Ghomi, M.A. Ghasemzadeh, Zinc oxide nanoparticles: a highly efficient and readily recyclable catalyst for the synthesis of xanthenes, Chin. Chem. Lett. 23 (2012) 1225-1229.
-
[38] B. Das, B. Ravikanth, R. Ramu, K. Laxminarayana, B.V. Rao, Iodine catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes, J. Mol. Catal. A: Chem. 255 (2006) 74-77.[38] B. Das, B. Ravikanth, R. Ramu, K. Laxminarayana, B.V. Rao, Iodine catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes, J. Mol. Catal. A: Chem. 255 (2006) 74-77.
-
[39] A.P. Mohamed, P.J. Vaderapura, Molecular iodine catalyzed synthesis of aryl-14Hdibenzo[a,j]xanthenes under solvent-free condition, Bioorg. Med. Chem. Lett. 17 (2007) 621-623.[39] A.P. Mohamed, P.J. Vaderapura, Molecular iodine catalyzed synthesis of aryl-14Hdibenzo[a,j]xanthenes under solvent-free condition, Bioorg. Med. Chem. Lett. 17 (2007) 621-623.
-
[40] M. Mohammadpour Amini, M. Seyyedhamzeh, A. Bazgir, Heteropolyacid: an efficient and eco-friendly catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]- xanthene, Appl. Catal. A: Gen. 323 (2007) 242-245.[40] M. Mohammadpour Amini, M. Seyyedhamzeh, A. Bazgir, Heteropolyacid: an efficient and eco-friendly catalyst for the synthesis of 14-aryl-14H-dibenzo[a,j]- xanthene, Appl. Catal. A: Gen. 323 (2007) 242-245.
-
[41] M.M. Heravi, Kh. Bakhtiari, Z. Daro@gheha, F.F. Bamoharram, Facile heteropolyacid- promoted synthesis of 14-substituted-14-H-dibenzo[a,j] xanthene derivatives under solvent-free conditions, J. Mol. Catal. A: Chem. 273 (2007) 99-101.[41] M.M. Heravi, Kh. Bakhtiari, Z. Daro@gheha, F.F. Bamoharram, Facile heteropolyacid- promoted synthesis of 14-substituted-14-H-dibenzo[a,j] xanthene derivatives under solvent-free conditions, J. Mol. Catal. A: Chem. 273 (2007) 99-101.
-
[42] H.R. Shaterian, M. Ghashang, A. Hassankhani, One-pot synthesis of aryl 14Hdibenzo[a,j]xanthene leuco-dye derivatives, Dyes Pigm. 76 (2008) 564-568.[42] H.R. Shaterian, M. Ghashang, A. Hassankhani, One-pot synthesis of aryl 14Hdibenzo[a,j]xanthene leuco-dye derivatives, Dyes Pigm. 76 (2008) 564-568.
-
[43] M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Solvent-free synthesis of aryl-14Hdibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst, Dyes Pigm. 76 (2008) 836-839.[43] M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Solvent-free synthesis of aryl-14Hdibenzo[a,j]xanthenes and 1,8-dioxo-octahydro-xanthenes using silica sulfuric acid as catalyst, Dyes Pigm. 76 (2008) 836-839.
-
[44] S. Ko, C.F. Yao, Heterogeneous catalyst: amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes under solvent-free conditions, Tetrahedron Lett. 47 (2006) 8827-8829.[44] S. Ko, C.F. Yao, Heterogeneous catalyst: amberlyst-15 catalyzes the synthesis of 14-substituted-14H-dibenzo[a,j]xanthenes under solvent-free conditions, Tetrahedron Lett. 47 (2006) 8827-8829.
-
[45] B.F. Mirjalili, A. Bamoniri, A. Akbari, N. Taghavinia, Nano-TiO2: an eco-friendly and re-usable catalyst for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]- xanthenes, J. Iran. Chem. Soc. 8 (2011) S129-S134.[45] B.F. Mirjalili, A. Bamoniri, A. Akbari, N. Taghavinia, Nano-TiO2: an eco-friendly and re-usable catalyst for the synthesis of 14-aryl or alkyl-14H-dibenzo[a,j]- xanthenes, J. Iran. Chem. Soc. 8 (2011) S129-S134.
-
[46] M. Dabiri, M. Baghbanzadeh, M.S. Nikcheh, E. Arzroomchilar, Eco-friendly and efficient one-pot synthesis of alkyl- or aryl-14H-dibenzo[a,j]xanthenes in water, Bioorg. Med. Chem. Lett. 18 (2008) 436-438.[46] M. Dabiri, M. Baghbanzadeh, M.S. Nikcheh, E. Arzroomchilar, Eco-friendly and efficient one-pot synthesis of alkyl- or aryl-14H-dibenzo[a,j]xanthenes in water, Bioorg. Med. Chem. Lett. 18 (2008) 436-438.
-
[47] H.J. Zang, Y. Zhang, B.W. Cheng, Efficient one-pot synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]xanthen-11-one derivatives using NaHSO4 as catalyst in ionic liquid, Adv. Mater. Res. 113 (2010) 1993-1996.[47] H.J. Zang, Y. Zhang, B.W. Cheng, Efficient one-pot synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]xanthen-11-one derivatives using NaHSO4 as catalyst in ionic liquid, Adv. Mater. Res. 113 (2010) 1993-1996.
-
[48] A. Sharifi, M.S. Abaee, A. Tavakkoli, M. Mirzaei, A. Zolfaghari, Facile montmorillonite k-10-supported synthesis of xanthene derivatives under microwave and thermal conditions, Synth. Commun. 38 (2008) 2958-2966.[48] A. Sharifi, M.S. Abaee, A. Tavakkoli, M. Mirzaei, A. Zolfaghari, Facile montmorillonite k-10-supported synthesis of xanthene derivatives under microwave and thermal conditions, Synth. Commun. 38 (2008) 2958-2966.
-
[49] A.R. Khosropour,M.M. Khodaei, H.Moghannian, A facile, simple and convenient method for the synthesis of 14-alkyl or aryl-14-H-dibenzo[a,j]xanthenes catalyzed by pTSA in solution and solvent-free conditions, Synlett (2005) 955- 958.[49] A.R. Khosropour,M.M. Khodaei, H.Moghannian, A facile, simple and convenient method for the synthesis of 14-alkyl or aryl-14-H-dibenzo[a,j]xanthenes catalyzed by pTSA in solution and solvent-free conditions, Synlett (2005) 955- 958.
-
[50] N.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Wet cyanuric chloride catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes, Catal Commun. 8 (2007) 1595-1598.[50] N.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Wet cyanuric chloride catalyzed simple and efficient synthesis of 14-aryl or alkyl-14-H-dibenzo[a,j]xanthenes, Catal Commun. 8 (2007) 1595-1598.
-
[51] S. Allameh, A. Davoodnia, A. Khojastehnezhad, An efficient and eco-friendly synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes using H4[SiW12O40] as a heterogeneous and reusable catalyst under solvent-free conditions, Chin. Chem. Lett. 23 (2012) 17-20.[51] S. Allameh, A. Davoodnia, A. Khojastehnezhad, An efficient and eco-friendly synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes using H4[SiW12O40] as a heterogeneous and reusable catalyst under solvent-free conditions, Chin. Chem. Lett. 23 (2012) 17-20.
-
[52] W. Su, D. Yang, C. Jin, B. Zhang, Yb(OTf)3 catalyzed condensation reaction of β-naphthol and aldehyde in ionic liquids: a green synthesis of aryl-14H-dibenzo[a,j]xanthenes, Tetrahedron Lett. 49 (2008) 3391-3394.[52] W. Su, D. Yang, C. Jin, B. Zhang, Yb(OTf)3 catalyzed condensation reaction of β-naphthol and aldehyde in ionic liquids: a green synthesis of aryl-14H-dibenzo[a,j]xanthenes, Tetrahedron Lett. 49 (2008) 3391-3394.
-
[53] F. Shirini, N.G. Khaligh, Succinimide-N-sulfonic acid: an efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions, Dyes Pigm. 95 (2012) 789-794.[53] F. Shirini, N.G. Khaligh, Succinimide-N-sulfonic acid: an efficient catalyst for the synthesis of xanthene derivatives under solvent-free conditions, Dyes Pigm. 95 (2012) 789-794.
-
[54] F. Shirini, N.G. Khaligh, S. Akbari-Dadamahaleh, Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogenfree and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes, J. Mol. Catal. A: Chem. 365 (2012) 15-23.[54] F. Shirini, N.G. Khaligh, S. Akbari-Dadamahaleh, Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogenfree and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes, J. Mol. Catal. A: Chem. 365 (2012) 15-23.
-
[55] F. Shirini, N.G. Khaligh, 1,3-Disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable ionic liquid catalyst for the N-Boc protection of amines, J. Mol. Liq. 177 (2013) 386-393.[55] F. Shirini, N.G. Khaligh, 1,3-Disulfonic acid imidazolium hydrogen sulfate as an efficient and reusable ionic liquid catalyst for the N-Boc protection of amines, J. Mol. Liq. 177 (2013) 386-393.
-
[56] L. Khazdooz, A. Zarei, A.R. Hajipour, N. Sheikhan, A study for the synthesis of dibenzo [a,j] xanthenes and 1-amidoalkyl 2-naphthols catalyzed by [Hmim][HSO4] as a green, efficient and reusable catalyst under solvent-free conditions, Iran. J. Catal. 1 (2011) 1-10.[56] L. Khazdooz, A. Zarei, A.R. Hajipour, N. Sheikhan, A study for the synthesis of dibenzo [a,j] xanthenes and 1-amidoalkyl 2-naphthols catalyzed by [Hmim][HSO4] as a green, efficient and reusable catalyst under solvent-free conditions, Iran. J. Catal. 1 (2011) 1-10.
-
[57] G.H. Mahdavinia, S. Rostamizadeh, A.M. Amani, Z. Emdadi, Ultrasound-promoted greener synthesis of aryl-14-H-dibenzo[a,j]xanthenes catalyzed by NH4H2PO4/ SiO2 in water, Ultrason. Sonochem. 16 (2009) 7-10.[57] G.H. Mahdavinia, S. Rostamizadeh, A.M. Amani, Z. Emdadi, Ultrasound-promoted greener synthesis of aryl-14-H-dibenzo[a,j]xanthenes catalyzed by NH4H2PO4/ SiO2 in water, Ultrason. Sonochem. 16 (2009) 7-10.
-
[58] B. Maleki, M. Gholizadeh, Z. Sepehr, 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[a]xanthene-11-one derivatives under solvent-free conditions, Bull. Korean Chem. Soc. 32 (2011) 1697-1702.[58] B. Maleki, M. Gholizadeh, Z. Sepehr, 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[a]xanthene-11-one derivatives under solvent-free conditions, Bull. Korean Chem. Soc. 32 (2011) 1697-1702.
-
[59] H. Hashemi, A.R. Sardarian, 4-Dodecylbenzenesulfonic acid (DBSA) as an efficient and recyclable catalyst for synthesis of 14-aryl- and 14-alkyl-14-Hdibenzo[a,j]xanthenes under solvent-free conditions, Iran. J. Sci. Technol. A1 (2013) 75-82.[59] H. Hashemi, A.R. Sardarian, 4-Dodecylbenzenesulfonic acid (DBSA) as an efficient and recyclable catalyst for synthesis of 14-aryl- and 14-alkyl-14-Hdibenzo[a,j]xanthenes under solvent-free conditions, Iran. J. Sci. Technol. A1 (2013) 75-82.
-
[60] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, et al., Organocatalyst trityl chloride efficiently promoted the solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones by in situ formation of carbocationic system in neutral media, Catal. Commun. 20 (2012) 54-57.[60] A. Khazaei, M.A. Zolfigol, A.R. Moosavi-Zare, et al., Organocatalyst trityl chloride efficiently promoted the solvent-free synthesis of 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-ones by in situ formation of carbocationic system in neutral media, Catal. Commun. 20 (2012) 54-57.
-
[61] G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, An efficient one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11-dione derivatives under solvent free condition, Tetrahedron 65 (2009) 7129-7134.[61] G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, An efficient one-pot synthesis of tetrahydrobenzo[a]xanthene-11-one and diazabenzo[a]anthracene-9,11-dione derivatives under solvent free condition, Tetrahedron 65 (2009) 7129-7134.
-
[62] M.M. Heravi, H. Alinejhad, K. Bakhtiari, H.A. Oskooie, Sulfamic acid catalyzed solvent-free synthesis of 10-aryl-7,7-dimethyl-6,7,8,10-tetrahydro-9H-[1,3]- dioxolo [4,5-b]xanthen-9-ones and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro- 11H-benzo[a]xanthen-11-ones, Mol. Divers. 14 (2010) 621-626.[62] M.M. Heravi, H. Alinejhad, K. Bakhtiari, H.A. Oskooie, Sulfamic acid catalyzed solvent-free synthesis of 10-aryl-7,7-dimethyl-6,7,8,10-tetrahydro-9H-[1,3]- dioxolo [4,5-b]xanthen-9-ones and 12-aryl-9,9-dimethyl-8,9,10,12-tetrahydro- 11H-benzo[a]xanthen-11-ones, Mol. Divers. 14 (2010) 621-626.
-
[63] F. Shirini, S. Akbari-Dadamahaleh, A. Mohammad-Khah, A.R. Aliakbar, Rice husk: a mild, efficient, green and recyclable catalyst for the synthesis of 12-aryl- 8,9,10,12-tetrahydro[a]xanthene-11-ones and quinoxaline derivatives, C.R. Chim. 16 (2013) 207-216.[63] F. Shirini, S. Akbari-Dadamahaleh, A. Mohammad-Khah, A.R. Aliakbar, Rice husk: a mild, efficient, green and recyclable catalyst for the synthesis of 12-aryl- 8,9,10,12-tetrahydro[a]xanthene-11-ones and quinoxaline derivatives, C.R. Chim. 16 (2013) 207-216.
-
[64] K. Venkatesan, S.S. Pujari, R.J. Lahoti, K.V. Srinivasan, An efficient synthesis of 1,8- dioxo-octahydro-xanthene derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation, Ultrason. Sonochem. 15 (2008) 548-553.[64] K. Venkatesan, S.S. Pujari, R.J. Lahoti, K.V. Srinivasan, An efficient synthesis of 1,8- dioxo-octahydro-xanthene derivatives promoted by a room temperature ionic liquid at ambient conditions under ultrasound irradiation, Ultrason. Sonochem. 15 (2008) 548-553.
-
[65] S. Kokkirala, N.M. Sabbavarapu, V.D.N. Yadavalli, b-Cyclodextrin mediated synthesis of 1,8-dioxooctahydroxanthenes in water, Eur. J. Chem. 2 (2011) 272-275.[65] S. Kokkirala, N.M. Sabbavarapu, V.D.N. Yadavalli, b-Cyclodextrin mediated synthesis of 1,8-dioxooctahydroxanthenes in water, Eur. J. Chem. 2 (2011) 272-275.
-
[66] A. Zare, A.R. Moosavi-Zare, M. Merajoddin, et al., Ionic liquid triethylaminebonded sulfonic acid {[Et3N-SO3H]Cl} as a novel, highly efficient and homogeneous catalyst for the synthesis of b-acetamido ketones, 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes, J. Mol. Liq. 167 (2012) 69-77.[66] A. Zare, A.R. Moosavi-Zare, M. Merajoddin, et al., Ionic liquid triethylaminebonded sulfonic acid {[Et3N-SO3H]Cl} as a novel, highly efficient and homogeneous catalyst for the synthesis of b-acetamido ketones, 1,8-dioxo-octahydroxanthenes and 14-aryl-14H-dibenzo[a,j]xanthenes, J. Mol. Liq. 167 (2012) 69-77.
-
[67] S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, G. Amiri, H. Sepehrian, Ultrasound promoted rapid and green synthesis of 1,8-dioxo-octahydroxanthenes derivatives using nanosized MCM-41-SO3H as a nanoreactor, nanocatalyst in aqueous media, Ultrason. Sonochem. 17 (2010) 306-309.[67] S. Rostamizadeh, A.M. Amani, G.H. Mahdavinia, G. Amiri, H. Sepehrian, Ultrasound promoted rapid and green synthesis of 1,8-dioxo-octahydroxanthenes derivatives using nanosized MCM-41-SO3H as a nanoreactor, nanocatalyst in aqueous media, Ultrason. Sonochem. 17 (2010) 306-309.
-
[68] M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, et al., Preparation of various xanthene derivatives over sulfonic acid functionalized imidazolium salts (SAFIS) as novel, highly efficient and reusable catalysts, C.R. Chim. 15 (2012) 719-736.[68] M.A. Zolfigol, V. Khakyzadeh, A.R. Moosavi-Zare, et al., Preparation of various xanthene derivatives over sulfonic acid functionalized imidazolium salts (SAFIS) as novel, highly efficient and reusable catalysts, C.R. Chim. 15 (2012) 719-736.
-
[69] K. Gong, D. Fang, H.L. Wang, X.L. Zhou, Z.L. Liu, The one-pot synthesis of 14-alkylor aryl-14H-dibenzo[a,j]xanthenes catalyzed by task-specific ionic liquid, Dyes Pigm. 80 (2009) 30-33.[69] K. Gong, D. Fang, H.L. Wang, X.L. Zhou, Z.L. Liu, The one-pot synthesis of 14-alkylor aryl-14H-dibenzo[a,j]xanthenes catalyzed by task-specific ionic liquid, Dyes Pigm. 80 (2009) 30-33.
-
[70] D. Kundu, A. Majee, A. Hajra, Task-specific ionic liquid catalyzed efficient microwave- assisted synthesis of 12-alkyl or aryl-8,9,10,12-tetrahydrobenzo[a]xanthen- 11-ones under solvent-free conditions, Green Chem. Lett. Rev. 4 (2011) 205-209.[70] D. Kundu, A. Majee, A. Hajra, Task-specific ionic liquid catalyzed efficient microwave- assisted synthesis of 12-alkyl or aryl-8,9,10,12-tetrahydrobenzo[a]xanthen- 11-ones under solvent-free conditions, Green Chem. Lett. Rev. 4 (2011) 205-209.
-
[71] B. Janardhan, S. Vijaya Laxmi, B. Rajitha, An efficient synthesis of 12-aryl- 8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones using (4-sulfobutyl)tris(4-sulfophenyl) phosphonium hydrogen sulphate as catalyst under neat conditions, J. Chem. Pharm. Res. 4 (2012) 519-525.[71] B. Janardhan, S. Vijaya Laxmi, B. Rajitha, An efficient synthesis of 12-aryl- 8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones using (4-sulfobutyl)tris(4-sulfophenyl) phosphonium hydrogen sulphate as catalyst under neat conditions, J. Chem. Pharm. Res. 4 (2012) 519-525.
-
[72] J.M. Khurana, D. Magoo, pTSA-catalyzed one-pot synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]xanthen-11-ones in ionic liquid and neat conditions, Tetrahedron Lett. 50 (2009) 4777-4780.[72] J.M. Khurana, D. Magoo, pTSA-catalyzed one-pot synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]xanthen-11-ones in ionic liquid and neat conditions, Tetrahedron Lett. 50 (2009) 4777-4780.
-
[73] A. Zare, R. Khanivar, M. Hatami, et al., Efficient synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]-xanthen-11-ones using ionic liquid pyrazinium di(hydrogen sulfate) {Py(HSO4)2} as a novel, green and homogeneous catalyst, J. Mex. Chem. Soc. 56 (2012) 389-394.[73] A. Zare, R. Khanivar, M. Hatami, et al., Efficient synthesis of 12-aryl-8,9,10,12- tetrahydrobenzo[a]-xanthen-11-ones using ionic liquid pyrazinium di(hydrogen sulfate) {Py(HSO4)2} as a novel, green and homogeneous catalyst, J. Mex. Chem. Soc. 56 (2012) 389-394.
-
[74] A. Zare, R. Khanivar, M. Merajoddin, et al., Triethylamine-bonded sulfonic acid {[Et3N-SO3H]Cl} as an efficient and homogeneous catalyst for the synthesis of 12- aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones, Iran. J. Catal. 2 (2012) 107- 114.[74] A. Zare, R. Khanivar, M. Merajoddin, et al., Triethylamine-bonded sulfonic acid {[Et3N-SO3H]Cl} as an efficient and homogeneous catalyst for the synthesis of 12- aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones, Iran. J. Catal. 2 (2012) 107- 114.
-
[75] K. Niknam, M. Damya, 1-Butyl-3-methylimidazolium hydrogen sulfate[bmim]HSO4: an efficient reusable acidic ionic liquid for the synthesis of 1,8- dioxo-octahydroxanthenes, J. Chin. Chem. Soc. 56 (2009) 659-665.[75] K. Niknam, M. Damya, 1-Butyl-3-methylimidazolium hydrogen sulfate[bmim]HSO4: an efficient reusable acidic ionic liquid for the synthesis of 1,8- dioxo-octahydroxanthenes, J. Chin. Chem. Soc. 56 (2009) 659-665.
-
[76] M. Dabiri, M. Baghbanzadeh, E. Arzroomchilar, 1-Methylimidazolium triflouroacetate ([Hmim]TFA): an efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines, Catal. Commun. 9 (2008) 939.[76] M. Dabiri, M. Baghbanzadeh, E. Arzroomchilar, 1-Methylimidazolium triflouroacetate ([Hmim]TFA): an efficient reusable acidic ionic liquid for the synthesis of 1,8-dioxo-octahydroxanthenes and 1,8-dioxo-decahydroacridines, Catal. Commun. 9 (2008) 939.
-
[77] M. Kalantari, Synthesis of 1,8-dioxo-octahydroxanthenes and bis(indolyl)- methanes catalyzed by [Et3NH][H2PO4] as a cheap and mild acidic ionic liquid, Arabian J. Chem. 5 (2012) 319-323.[77] M. Kalantari, Synthesis of 1,8-dioxo-octahydroxanthenes and bis(indolyl)- methanes catalyzed by [Et3NH][H2PO4] as a cheap and mild acidic ionic liquid, Arabian J. Chem. 5 (2012) 319-323.
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