Abstract
A wide variety of 3-arylbenzo[f]quinoline-1,2-dicarboxylates and their dehydro derivatives have been synthesized by one-pot, three-component reaction of an aromatic aldehyde, naphthalene-2-amine, and dimethyl but-2-ynedioate in the presence of SnCl2 under reflux in acetonitrile. This procedure has several advantages, for example high yield, short reaction time, easy work-up, little pollution, and low price of the catalyst.
Similar content being viewed by others
References
I. Domling, Angew. Chem. Int. Ed. 39, 3168 (2000)
I. Ugi, Adv. Synth. Catal. 339, 499 (1997)
N.K. Terret, M. Gardener, D.W. Gordon, R.J. Kobylecki, J. Steele, Tetrahedron 51, 8135 (1995)
A.T. Khan, T. Parvin, L.H. Choudury, J. Org. Chem. 73, 8398 (2008)
X.S. Wang, J. Zhou, K. Yang, C.S. Yao, Tetrahedron Lett. 51, 5721 (2010)
G. Maiti, R. Karmaker, U. Kayal, Tetrahedron Lett. 54, 2920 (2013)
G. Selvi, S.P. Rajendran, J. Asian Chem. 16, 1017 (2004)
R.P. Bahuguna, B.C. Joshi, Indian J. Heterocycl. Chem. 3, 265 (1994)
B.A. Carr, M.R. Franklin, Xenobiotica 28, 949 (1998)
H.T. Le, J.G. Lamb, M.R. Franklin, J. Biochem. Toxicol. 11, 297 (1996)
R.P. Bahuguna, B.C. Joshi, H.N. Mangal, J. Indian, Chem. Soc. 69, 401 (1992)
F. S. Mikhailitsyn, N. P. Kozyreva, S. A. Rabinovich, Y. V. Maksakovskaya, I. M. Kulikovskaya, N. R. Dadasheva, M. N. Lebedeva, A. F. Bekhli, N. D. Lychko, N. A. Uvarova, Med. Parazitol. 50–53 (1992); Chem. Abstr. 117, 251317 (1992)
J. Nozulak, J.M. Vigouret, A.L. Jaton, A. Hofmann, A.R. Dravid, H.P. Weber, H.O. Kalkman, M.D. Walkinshaw, J. Med. Chem. 35, 480 (1992)
J. Szmuszkovicz, W.H. Darlington, P.F. Von Voigtlander, WO8804292A1. Chem. Abstr. 110, 75335 (1988)
P. Buonora, J.C. Olsen, T. Oh, Tetrahedron 57, 6099 (2001)
K.A. Jørgensen, Angew. Chem. Int. Ed. 39, 3558 (2000)
H. M. Hosni, W. M. Basyouni, H. A. El-Nahas, J. Chem. Res. Synop. 646 (1999)
J. W. Daly, T. F. Spande, in Alkaloids: Chemical and Biological Perspectives, ed. by S. W. Pelletier (Wiley: New York, NY.4, 1, 1986)
G. B. Fodor, B. Colasanti, in Alkaloids: Chemical and Biological Perspectives, ed. by S.W. Pelletier, (Wiley: New York, NY. 3, 1, 1983)
D.L. Boger, M. Patel, Prog. Heterocycl. Chem. 1, 1 (1989)
H. Suschitzky, E. F. V. Scriven (eds.), (Pergamon: New York, NY, 1, 1, 1989)
T. Kametani, S. Hibino, Adv. Heterocycl. Chem. 42, 246 (1987)
G. Bhargava, C. Mohan, M.P. Mahajan, Tetrahedron 64, 3017 (2008)
K. Takasu, N. Shindoh, H. Tokuyama, M. Ihara, Tetrahedron 62, 11900 (2006)
R.D.R.S. Manian, J. Jayashankaran, R. Ramesh, R. Raghunathan, Tetrahedron Lett. 47, 7571 (2006)
J.S. Yadav, B.V.S. Reddy, G. Kondaji, S. Sowjanya, K. Nagaiah, Mol. Catal. A. Chem. 258, 361 (2006)
A.H.G.P. Prenzel, N. Deppermann, W. Maison, Org. Lett. 8, 1681 (2006)
Y. Zhou, X. Jia, R. Li, Z. Liu, Z. Liu, L. Wu, Tetrahedron Lett. 46, 8937 (2005)
M. Rodŕiguez, M.E. Ochoa, R. Santillan, N. Farfán, V.J. Barba, Organomet. Chem. 690, 2975 (2005)
A.-B. Garćia, C. Valdés, M.-P. Cabal, Tetrahedron Lett. 45, 4357 (2004)
B. Danieli, G. Lesma, D. Passarella, P. Piacenti, A. Sacchetti, A. Silvani, A. Virdis, Tetrahedron Lett. 43, 7155 (2002)
H.J. Zang, Y. Zhang, Y.M. Mo, B.W. Cheng, Synth. Commun. 41, 3207 (2011)
A.A. Kudale, J.K. Kendall, D.O. Miller, J.L. Collins, G.J. Bodwell, J. Org. Chem. 73, 8437 (2008)
Acknowledgments
The project was supported by the National Natural Science Foundation of China (No. 21346001, 21406166) and the Tianjin National Natural Science Foundation (No. 11JCZDJC21300).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Yan, Q., Zang, H., Feng, J. et al. An efficient method for synthesis of 3-arylbenzo[f]quinoline-1,2-dicarboxylates catalyzed by SnCl2 . Res Chem Intermed 41, 6967–6974 (2015). https://doi.org/10.1007/s11164-014-1791-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-014-1791-6