Abstract
A simple, efficient, and environmentally benign route was developed for the preparation of 14-aryl or alkyl-14H-dibenzo[a,j]xanthene, 1,8-dioxo-octahydroxanthene and 12-aryl—8,9,10,12-tetrahydrobenzo[a]xanthene-11-ones from condensation of various aldehydes with (i) β-naphthol, (ii) cyclic 1,3-dicarbonyl compounds and (iii) β-naphthol and cyclic 1,3-dicarbonyl compounds, using novel polymeric catalyst [poly(AMPS-co-AA)] under solvent-free conditions. Use of easily available catalyst, shorter reaction times, better yields, simplicity of the reaction, heterogeneous system, and easy work-up are the advantages of the present method.
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M.A. El-Brashy, M.E. Metwally, F.A. El-Sepai, Farmaco 59, 809 (2004)
J.M. Jamison, K. Krabill, A. Hatwalkar, Cell. Bio. Intern. Reports 14, 1075 (1990)
K. Chibale, M. Visser, D.V. Schalkwyk, P.S. Smith, A. Saravanamuthu, A.H. Fairlamb, Tetrahedron 59, 2289 (2003)
C.G. Knight, T. Stephens, Biochem. J. 258, 683689 (1989)
X. Guan, X. Liu, Z. Su, P. Liu, React. Funct. Polym. 66, 1227 (2006)
M. Ahmad, T.A. King, B.H. Cha, J. Lee, J. Phys. D Appl. Phys. 35, 1473 (2002)
R.M. Ion, A. Frackowiak, K. Wiktorowicz, Acta Biochim. Pol. 45, 833 (1998)
B.B. Bhowmik, P. Ganguly, Mol. Biomol. Spect. 61, 1997 (2005)
G. Saint-Ruf, H.T. Hieu, J.P. Poupelin, Naturwissenschaften 62, 584 (1975)
Y.M. Shchekotikhim, T.G. Nikolaeva, Chem. Het. Comp. 42, 28 (2006)
S. Hatakeyama, N. Ochi, H. Numata, S. Takamo, Chem. Commun. (1988) 1202
S.V. Ley, I.R. Baxendale, R.N. Bream, P.S. Jackson, A.G. Leach, D.A. Longbottom, M. Nesi, J.S. Scott, R.I. Storer, S.J. Taylor, J. Chem. Soc. Perkin Trans. 1(23), 3815 (2000)
A. Kirschning, H. Monenschein, R. Wittenberg, Ang. Chem. Int. Ed. 40, 650 (2001)
P. Hodge, Curr. Opinion Chem. Bio. 7, 362 (2003)
P.J. Comina, A.K. Beck, D. Seebach, Org. Process Res. Dev. 2, 18 (1998)
A. Pourjavadi, H. Salimi, S. Barzegar, B. Eftekhari-Sis, Acta Chim. Slov. 54, 140 (2007)
D.W. Knight, P.B. Little, Synlett 10, 1141 (1998)
D.W. Knight, P.B. Little, J. Chem. Soc. Perkin Trans 1(15), 1771 (2001)
A. Bekaert, J. Andrieux, M. Plat, Tetrahedron Lett. 33, 2805 (1992)
A. Jha, J. Beal, Tetrahedron Lett. 45, 8999 (2004)
C.W. Kuo, J.M. Fang, Synth. Commun. 31, 877 (2001)
P. Papini, R. Cimmarusti, Gazz. Chim. Ital. 77, 142 (1947)
R.N. Sen, N. Sarkar, J. Am. Chem. Soc. 47, 1079 (1925)
K. Ota, T. Kito, Bull. Chem. Soc. Jpn. 49, 1167 (1976)
A. Zarei, A.R. Hajipour, L. Khazdooz, Dyes Pigm. 85, 133 (2010)
H.R. Shaterian, M. Ghashang, A. Hassankhani, Dyes Pigm. 6, 564 (2008)
M. Seyyedhamzeh, P. Mirzaei, A. Bazgir, Dyes Pigm. 76, 836 (2008)
Z. Karimi-Jaberi, M. Keshavarzi, Chin. Chem. Lett. 21, 547 (2010)
B.B. Mirjalili, A. Bamoniri, A. Akbari, Tetrahedron Lett. 49, 6454 (2008)
N.D. Kokare, J.N. Sangshetti, D.B. Shinde, Chin. Chem. Lett. 19, 1186 (2008)
A.K. Bhattacharya, K.C. Rana, M. Mujahid, I. Sehar, A.K. Saxena, Bioorg. Med. Chem. Lett. 19, 5590 (2009)
M. Dabiri, M. Baghbanzadeh, M. Shakouri Nicheh, E. Arzroomchilar, Bioorg. Med. Chem. Lett. 18, 436 (2008)
S. Kantevari, M.V. Chary, A.P.K. Das, S.V.N. Vuppalupati, N. Lingaiah, Catal. Commun. 9, 1575 (2008)
K. Gong, D. Fang, H.L. Wang, X.L. Zhou, Z.L. Liu, Dyes Pigm. 80, 30 (2009)
A.K. Bhattacharya, K.C. Rana, Mendeleev Commun. 17, 247 (2007)
H.Y. Lu, J.J. Li, Z.H. Zhang, Appl. Orgnometal. Chem. 23, 165 (2009)
A. John, R.J.P. Yadav, S. Palaniappan, J. Mol. Catal. A: Chem. 248, 121 (2006)
Z.H. Zhang, Y.H. Liu, Catal. Commun. 9, 1715 (2008)
M.A. Bigdeli, F. Nemati, G.H. Mahdavinia, H. Doostmohammadi, Chin. Chem. Lett. 20, 1275 (2009)
B. Das, P. Thirupathi, K.R. Reddy, B. Ravikanth, L. Nagarapu, Catal. Commun. 8, 535 (2007)
M. Khurana, D. Magoo, Tetrahedron Lett. 50, 4777 (2009)
G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, Tetrahedron 65, 7129 (2009)
R. Kumar, G.C. Nandi, R.K. Verma, M.S. Singh, Tetrahedron Lett. 51, 442 (2010)
J. Li, W. Tang, L. Lu, W. Su, Tetrahedron Lett. 49, 7117 (2008)
J. Li, L. Lu, W. Su, Tetrahedron Lett. 51, 2434 (2010)
Z.H. Zhang, H.J. Wang, X.Q. Ren, Y.Y. Zhang, Monatsh. Chem. 10, 1481 (2009)
K. Niknam, M. Damya, J. Chin. Chem. Soc. 56, 659 (2009)
J.V. Mahdav, Y.T. Reddy, P.N. Reddy, M.N. Reddy, S. Kuarm, P.A. Crooks, B. Rajitha, J. Mol. Catal. A: Chem. 304, 85 (2009)
M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, J. Mol. Catal. A: Chem. 275, 25 (2007)
M.M. Heravi, K. Bakhtiari, Z. Daroogheha, F.F. Bamoharram, J. Mol. Catal. A: Chem. 273, 99 (2007)
M.A. Bigdeli, M.M. Heravi, G.H. Mahdavinia, Catal. Commun. 8, 595 (2007)
Z.H. Zhang, P. Zhang, S.H. Yang, H.J. Wang, J. Deng, J. Chem. Sci. 122, 427 (2010)
N. Karimi, H. Abdi-Oskooie, M.M. Heravi, L. Tahershamsi, Synth. Commun. 41, 307 (2011)
B.F. Mirjalilia, A. Bamonirib, A. Akbari, N. Taghavinia, J. Iran. Chem. Soc. 8, S129 (2011)
M.R. Poor Heravi, J. Iran. Chem. Soc. 6, 483 (2009)
D. Azarifar, B. Maleki, Heterocycles 65, 865 (2005)
B. Maleki, H. Salahabadi, M. Khodaverdian-Moghaddam, Acta Chim. Slov. 3, 741 (2010)
M.A. Zolfigol, D. Azarifar, B. Maleki, Tetrahedron Lett. 45, 2181 (2004)
B. Maleki, Coll. Czech. Chem. Commun. 76, 27 (2011)
B. Maleki, M. Gholizadeh, Z. Sepehr, Bull. Korean Chem. Soc. 32, 1697 (2011)
M. Hosseini-Sarvari, J. Iran. Chem. Soc. 8, S119 (2011)
R. Ghorbani-Vaghei, S.M. Malaekehpoor, J. Iran. Chem. Soc. 7, 957 (2010)
A.R. Hajipoura, Y. Ghayeb, N. Sheikhan, J. Iran. Chem. Soc. 7, 447 (2010)
B. Tamami, H. Firouzabadi, F. Ebrahimzadeh, A. Fadavi, J. Iran. Chem. Soc. 6, 722 (2009)
A. Sharifi, M.S. Abaee, A. Tavakkoli, M. Mirzaei, J. Iran. Chem. Soc. 5, S113 (2008)
A. Domling, I. Ugi, Chem. Intl. Ed. 39, 3168 (2000)
S. Ghassamipour, A.R. Sardarian, J. Iran. Chem. Soc. 7, 237 (2010)
M. Hosseini-Sarvari, J. Iran. Chem. Soc. 5, S118 (2008)
M.A. Zolfigol, E. Kolvari, A. Abdoli, M. Shiri, Mol. Divers. 14, 809 (2010)
F. Shirini, M.A. Zolfigol, A.R. Abri, J. Iran. Chem. Soc. 5, 96 (2008)
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The authors are thankful to research council of Hakim Sabzevari University for financial support.
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Maleki, B., Barzegar, S., Sepehr, Z. et al. A novel polymeric catalyst for the one-pot synthesis of xanthene derivatives under solvent-free conditions. J IRAN CHEM SOC 9, 757–765 (2012). https://doi.org/10.1007/s13738-012-0092-5
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DOI: https://doi.org/10.1007/s13738-012-0092-5