Main Article Content
Abstract
A multicomponent condensation of aromatic aldehydes, β-naphthols and dimidone in 1-butyl-3- methylimidazolium bromide as a green catalyst produces xanthene derivatives in good to excellent yield. Using 1-butyl-3-methylimidazolium bromide as a very efficient, convenient, economical, recyclable, green catalyst for the synthesis under solvent free condition has been developed. This method is environmental benign and advantageous compared to conventional methods because reusability of the ionic liquids, simple work-up and high yields of products.
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References
- T. Hideo and J. Teruomi, Benzopyrano[2,3-b]xanthene Derivatives, Jpn. Patent, 56,005,480 (1981).
- J.P. Poupelin, G. Saint-Ruf, O. Foussard-blanpin, G. Narcisse, G. Uchida-Ernouf and R. Lacroix, Synthesis and Antiinflammatory Properties of Bis(2-hydroxy-1-naphthyl)methane Derivatives. I. Monosubstituted Derivatives, Eur. J. Med. Chem., 13, 67 (1978).
- R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes and G.J. Thomas, Pyrimidine Nucleosides, PCT Int. Appl. WO 9,706,178 (1997).
- C.G. Knight and T. Stephens, Xanthene-Dye-Labelled Phosphatidyl-ethanolamines as Probes of Interfacial pH Studies in Phospholipid Vesicles, Biochem. J., 45, 833 (1989).
- A. Banerjee and A.K. Mukherjee, Chemical Aspects of Santalin as a Histological Stain, Stain Technol., 56, 83 (1981); https://doi.org/10.3109/10520298109067286.
- S.M. Menchen, S.C. Benson, J.Y.L. Lam, W.-G. Zhen, D.Q. Sun, B.B. Rosenblum, S.H. Khan and M. Taing, Sulfonated Diarylrhodamine Dyes, US Patent, 6,583,168 (2003).
- O. Sirkencioglu, N. Talinli and A. Akar, Chemical Aspects of Santalin as a Histological Stain, J. Chem. Res. (S), 502 (1995).
- M. Ahmad, T.A. King, D.-K. Ko, B.H. Cha and J.J. Lee, Performance and Photostability of Xanthene and Pyrromethene Laser Dyes in Sol-Gel Phases, Phys. D. Appl. Phys., 35, 1473 (2002); https://doi.org/10.1088/0022-3727/35/13/303.
- R.-Z. Wang, L.-F. Zhang and Z.-S. Cui, Iodine-Catalyzed Synthesis of 12-Aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one Derivatives via Multicomponent Reaction, Synth. Commun., 39, 2101 (2009); https://doi.org/10.1080/00397910802638511.
- G.M. Nazeruddin and A.M.A. Al-Kadasi, Ultrasound Assisted One-Pot Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one Derivatives Using Chlorosulphonic Acid as a Catalyst under Solvent-Free Conditions, Res. J. Pharm. Biol. Chem. Sci., 2, 71 (2011).
- N. Karimi, H.A. Oskooie, M.M. Heravi and L. Tahershamsi, Caro's Acid-Silica Gel-Catalyzed One-Pot Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones, Synth. Commun., 41, 307 (2010); https://doi.org/10.1080/00397910903537372.
- L.-P. Mo and H.-L. Chen, One-Pot, Three-Component Condensation of Aldehydes, 2-Naphthol and 1,3-Dicarbonyl Compounds, J. Chin. Chem. Soc., 57, 157 (2010); https://doi.org/10.1002/jccs.201000025.
- H.-J. Wang, X.-Q. Ren, Y.-Y. Zhang and Z.-H. Zhang, Synthesis 12-Aryl or 12-Alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one Derivatives Catalyzed by Dodecatungstophosphoric Acid, J. Braz. Chem. Soc., 20, 1939 (2009); https://doi.org/10.1590/S0103-50532009001000025.
- Z.-H. Zhang, P. Zhang, S.-H. Yang, H.-J. Wang and J. Deng, Multi-component, Solvent-Free Synthesis of 12-Aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one Derivatives Catalysed by Cyanuric Chloride, J. Chem. Sci., 122, 427 (2010); https://doi.org/10.1007/s12039-010-0049-0.
- G.C. Nandi, S. Samai, R. Kumar and 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, 7129 (2009); https://doi.org/10.1016/j.tet.2009.06.024.
- J. Li, W. Tang, L. Lu and W. Su, Strontium Triflate Catalyzed One-Pot Condensation of b-Naphthol, Aldehydes and Cyclic 1,3-Dicarbonyl Compounds, Tetrahedron Lett., 49, 7117 (2008); https://doi.org/10.1016/j.tetlet.2008.09.129.
- P.V. Shinde, A.H. Kategaonkar, B.B. Shingate and M.S. Shingare, Surfactant Catalyzed Convenient and Greener Synthesis of Tetrahydrobenzo[a]-xanthene-11-ones at Ambient Temperature, Beilstein J. Org. Chem., 7, 53 (2011); https://doi.org/10.3762/bjoc.7.9.
- A. Zare, M. Mokhlesi, A. Hasaninejad and T. Hekmat-Zadeh, Solvent-Free Synthesis of 1,8-Dioxo-octahydroxanthenes and 14-Aryl-14H-dibenzo[a,j]xanthenes using Saccharin Sulfonic Acid as an Efficient and Green Catalyst, E-J. Chem., 9, 1854 (2012); https://doi.org/10.1155/2012/596862.
- A. Hassankhani, E. Mosaddegh and S.Y. Ebrahimipour, H4SiW12O40 Catalyzed One-Pot Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a] Xanthen-11-ones Under Solvent-Free Conditions, E-J. Chem., 9, 786 (2012); https://doi.org/10.1155/2012/930251.
References
T. Hideo and J. Teruomi, Benzopyrano[2,3-b]xanthene Derivatives, Jpn. Patent, 56,005,480 (1981).
J.P. Poupelin, G. Saint-Ruf, O. Foussard-blanpin, G. Narcisse, G. Uchida-Ernouf and R. Lacroix, Synthesis and Antiinflammatory Properties of Bis(2-hydroxy-1-naphthyl)methane Derivatives. I. Monosubstituted Derivatives, Eur. J. Med. Chem., 13, 67 (1978).
R.W. Lambert, J.A. Martin, J.H. Merrett, K.E.B. Parkes and G.J. Thomas, Pyrimidine Nucleosides, PCT Int. Appl. WO 9,706,178 (1997).
C.G. Knight and T. Stephens, Xanthene-Dye-Labelled Phosphatidyl-ethanolamines as Probes of Interfacial pH Studies in Phospholipid Vesicles, Biochem. J., 45, 833 (1989).
A. Banerjee and A.K. Mukherjee, Chemical Aspects of Santalin as a Histological Stain, Stain Technol., 56, 83 (1981); https://doi.org/10.3109/10520298109067286.
S.M. Menchen, S.C. Benson, J.Y.L. Lam, W.-G. Zhen, D.Q. Sun, B.B. Rosenblum, S.H. Khan and M. Taing, Sulfonated Diarylrhodamine Dyes, US Patent, 6,583,168 (2003).
O. Sirkencioglu, N. Talinli and A. Akar, Chemical Aspects of Santalin as a Histological Stain, J. Chem. Res. (S), 502 (1995).
M. Ahmad, T.A. King, D.-K. Ko, B.H. Cha and J.J. Lee, Performance and Photostability of Xanthene and Pyrromethene Laser Dyes in Sol-Gel Phases, Phys. D. Appl. Phys., 35, 1473 (2002); https://doi.org/10.1088/0022-3727/35/13/303.
R.-Z. Wang, L.-F. Zhang and Z.-S. Cui, Iodine-Catalyzed Synthesis of 12-Aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one Derivatives via Multicomponent Reaction, Synth. Commun., 39, 2101 (2009); https://doi.org/10.1080/00397910802638511.
G.M. Nazeruddin and A.M.A. Al-Kadasi, Ultrasound Assisted One-Pot Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one Derivatives Using Chlorosulphonic Acid as a Catalyst under Solvent-Free Conditions, Res. J. Pharm. Biol. Chem. Sci., 2, 71 (2011).
N. Karimi, H.A. Oskooie, M.M. Heravi and L. Tahershamsi, Caro's Acid-Silica Gel-Catalyzed One-Pot Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-ones, Synth. Commun., 41, 307 (2010); https://doi.org/10.1080/00397910903537372.
L.-P. Mo and H.-L. Chen, One-Pot, Three-Component Condensation of Aldehydes, 2-Naphthol and 1,3-Dicarbonyl Compounds, J. Chin. Chem. Soc., 57, 157 (2010); https://doi.org/10.1002/jccs.201000025.
H.-J. Wang, X.-Q. Ren, Y.-Y. Zhang and Z.-H. Zhang, Synthesis 12-Aryl or 12-Alkyl-8,9,10,12-tetrahydrobenzo[a]xanthen-11-one Derivatives Catalyzed by Dodecatungstophosphoric Acid, J. Braz. Chem. Soc., 20, 1939 (2009); https://doi.org/10.1590/S0103-50532009001000025.
Z.-H. Zhang, P. Zhang, S.-H. Yang, H.-J. Wang and J. Deng, Multi-component, Solvent-Free Synthesis of 12-Aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one Derivatives Catalysed by Cyanuric Chloride, J. Chem. Sci., 122, 427 (2010); https://doi.org/10.1007/s12039-010-0049-0.
G.C. Nandi, S. Samai, R. Kumar and 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, 7129 (2009); https://doi.org/10.1016/j.tet.2009.06.024.
J. Li, W. Tang, L. Lu and W. Su, Strontium Triflate Catalyzed One-Pot Condensation of b-Naphthol, Aldehydes and Cyclic 1,3-Dicarbonyl Compounds, Tetrahedron Lett., 49, 7117 (2008); https://doi.org/10.1016/j.tetlet.2008.09.129.
P.V. Shinde, A.H. Kategaonkar, B.B. Shingate and M.S. Shingare, Surfactant Catalyzed Convenient and Greener Synthesis of Tetrahydrobenzo[a]-xanthene-11-ones at Ambient Temperature, Beilstein J. Org. Chem., 7, 53 (2011); https://doi.org/10.3762/bjoc.7.9.
A. Zare, M. Mokhlesi, A. Hasaninejad and T. Hekmat-Zadeh, Solvent-Free Synthesis of 1,8-Dioxo-octahydroxanthenes and 14-Aryl-14H-dibenzo[a,j]xanthenes using Saccharin Sulfonic Acid as an Efficient and Green Catalyst, E-J. Chem., 9, 1854 (2012); https://doi.org/10.1155/2012/596862.
A. Hassankhani, E. Mosaddegh and S.Y. Ebrahimipour, H4SiW12O40 Catalyzed One-Pot Synthesis of 12-Aryl-8,9,10,12-tetrahydrobenzo[a] Xanthen-11-ones Under Solvent-Free Conditions, E-J. Chem., 9, 786 (2012); https://doi.org/10.1155/2012/930251.