Abstract
Ti–Al/Al2O3 nanocomposite catalyzed green and efficient synthesis of 2-amino-4H-chromen-5(6H)-ones via three-component condensation reaction of different aromatic aldehyde, malononitrile and dimedone in aqueous media. The reaction was preceded to completion within 30–90 min in 80–96 % yield at ambient temperature. The Ti–Al/Al2O3 nanocomposite was prepared by milling for 4 h and combustion synthesis at 800 °C in the air atmosphere. The catalyst was well characterized by X-ray diffraction, laser particle sizer and transmission electron microscopy. Its average particle size was found to be around 27 nm. Reusability of the system was assured carrying out multiple runs using the recycled catalyst.
Graphical abstract
Similar content being viewed by others
References
S.S. Chavan, M.S. Degani, Green. Chem. 14, 296 (2012)
A. Kumar, M.K. Gupta, M. Kumar, Green. Chem. 14, 290 (2012)
Q. Zhang, H. Su, J. Luo, Y. Wei, Green. Chem. 14, 201 (2012)
J. Hagen, Industrial catalysis: a practical approach, (Wiley-VCH: Weinheim, 1999)
W.A. Herrmann, B. Cornils, Angew. Chem. Int. Ed. Engl. 36, 1048 (1997)
N. Husing, U. Schubert, Angew. Chem. Int. Ed. Engl. 37, 22 (1998)
S. Wang, Y. Hu, R. Zong, Y. Tang, Z. Chen, W. Fan, Appl. Clay. Sci. 25, 49 (2004)
S.F. Wang, Y. Hu, Z.H. Lin, Z. Gui, Z.Z. Wang, Z.Y. Chen, W.C. Fan, Polym. Int. 52, 1045 (2003)
N. Claussen, D.E. Garcia, R. Jansen, J. Mater. Res. 11, 2884 (1996)
O.N. Senkov, M. Cavusoglu, F.H. Froes, Mater. Sci. Eng. A 300, 85 (2001)
G.R. Green, J.M. Evans, A.K. Vong, in Comprehensive Heterocyclic Chemistry II, ed. A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Vol. 5 (Pergamon Press, Oxford, 1995), p. 469
L.L. Andreani, E. Lapi, Bull. Chim. Fr. 99, 583 (1960)
Y.L. Zhang, B.Z. Chen, K.Q. Zheng, M.L. Xu, X.H. Lei, Yao. Xue. Xue. Bao. 17, 17 (1982)
Y.L. Zhang, B.Z. Chen, K.Q. Zheng, M.L. Xu, X.H. Lei, Chem. Abstr. 96, 135383e (1982)
L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28, 517 (1993)
E.C. Witte, P. Neubert, A. Roesch, Chem. Abstr. 104, 224915f (1986)
C.S. Konkoy, D.B. Fick, S.X. Cai, N.C.W. Lan, J.F.W. Keana, PCT. Int. Appl. WO. 00, 75123 (2000)
C.S. Konkoy, D.B. Fick, S.X. Cai, N.C.W. Lan, J.F.W. Keana, Chem. Abstr. 134, 29313a (2001)
S. Jin, A.Q. Wang, F.W. Shi, L.S. Han, L.B. Lin, T.S. Li, Arkivoc xiv, 78–86 (2006)
S. Jin, A.Q. Wang, X. Wang, J.S. Zhang, T.S. Li, Synlett, 5, 871–873 (2004)
I. Devi, P.J. Bhuyan, Tetrahedron. Lett. 45, 8625 (2004)
L.M. Wang, J.H. Shao, H. Tian, Y.H. Wang, B. Liu, J. Fluorine. Chem. 127, 97 (2006)
D.Q. Shi, S. Zhang, Q.Y. Zhuang, S.J. Tu, H.W. Hu, Chin. J. Org. Chem. 23, 877 (2003)
S. Balalaie, M. Bararjanian, A.M. Amani, B. Movassagh, Synlett, 2, 263–266 (2006)
R. Hekmatshoar, S. Majedi, K. Bakhtiari, Catal. Commun. 9, 307 (2008)
M.R. Islami, E. Mosaddegh, Phosphorus. Sulfur. Silicon. Relat. Elem. 184, 3134 (2009)
S.J. Tu, Y. Gao, C. Guo, D. Shi, Z. Lu, Synth. Commun. 32, 2137 (2002)
X.S. Wang, D.Q. Shi, S.J. Tu, C.S. Yao, Synth. Commun. 33, 119 (2003)
S. Balalaie, M. Sheikh-Ahmadi, M. Bararjanian, Catal. Commun. 8, 1724 (2007)
L. Fotouhi, M.M. Heravi, A. Fatehi, K. Bakhtiari, Tetrahedron. Lett. 48, 5379 (2007)
S. Gurumurthi, V. Sundari, R. Valliappan, EJ. Chem. 6, S466 (2009)
Y.Q. Peng, G.H. Song, Catal. Commun. 8, 111 (2007)
E. Mosaddegh, A. Hassankhani, Tetrahedron Lett 52, 488 (2011)
E. Mosaddegh, A. Hassankhani, Catal. Commun. 33, 70 (2013)
Acknowledgments
The authors thank the Graduate University of Advanced Technology, for partial financial support of this investigation.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Mosaddegh, E., Poshtiban, F., Hassankhani, A. et al. Synthesis and characterization of Ti–Al/Al2O3 nanocomposite and its application as heterogeneous catalyst in the green synthesis of 2-amino-4H-chromens. J IRAN CHEM SOC 11, 639–643 (2014). https://doi.org/10.1007/s13738-013-0334-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s13738-013-0334-1