Browse > Article
http://dx.doi.org/10.5012/jkcs.2012.56.6.712

A Simple and Clean Synthesis of Polysubstituted 2,6-Dicyanoanilines Catalyzed by KF/alumina  

Jain, Shubha (School of Studies in Chemistry, Vikram University)
Keshwal, Balwant S. (School of Studies in Chemistry, Vikram University)
Rajguru, Deepika (School of Studies in Chemistry, Vikram University)
Bhagwat, Vasant W. (School of Studies in Chemistry, Vikram University)
Publication Information
Abstract
A simple and clean synthesis of polysubstituted 2,6-dicyanoanilines has been developed via the reaction of arylidenemalonodinitriles with 1-arylethylidenemalonodinitriles in ethanol catalyzed by KF/alumina. Use of non-hazardous solid base as a catalyst, operational simplicity and improved product yields are the key advantages of the present protocol.
Keywords
Polysubstituted 2,6-dicyanoanilines; Heterogeneous catalyst; Synthesis;
Citations & Related Records
연도 인용수 순위
  • Reference
1 Raghukumar, V.; Murugan, P.; Ramakrishnan, V. T. Synth. Commun. 2001, 31, 3497.   DOI
2 Goel, A.; Singh, F. V. Tetrahedron Lett. 2005, 46, 5585   DOI
3 Andersen, N. G.; Maddaford, S. P.; Keay, B. A. J. Org. Chem. 1996, 61, 9556   DOI
4 Noyori, R. Chem. Soc. Rev. 1989, 18, 187   DOI
5 Yamamura, K.; Ono, S.; Ogoshi, H.; Masuda, H. Y.; Kuroda, Y. Synlett 1989, 18;
6 Yamamura, K.; Ono, S.; Tabushi, I. Tetrahedron Lett. 1988, 29, 1797.   DOI
7 Cui, S. L.; Lin, X. F.; Gang, W. Y. J. Org. Chem. 2005, 70, 2866.   DOI
8 Milart, P.; Wilamowski, J.; Sepiol, J. J. Tetrahedron 1998, 54, 15643.   DOI
9 Elgemei, G. E. H.; Elzanate, A. M.; Mansour, A. K. J. Chem. Soc. Perkin Trans. 1 1992, 1, 1073.
10 Victory, P. J.; Borrell, J. I.; Vidal-Ferran, A. Heterocycles 1993, 36, 769.   DOI
11 Victory, P.; Borrell, J. I.; Vidal- Ferran, A.; Seoane, C.; Soto, J. Tetrahedron Lett. 1991, 32, 5375.   DOI
12 Victory, P. J.; Borrell, J.; Vidal-Ferran, A.; Montenegro, E.; Jimeno, M. L. Heterocycles 1993, 36, 2273.   DOI
13 Xin, X.; Wang, Y.; Xu, W.; Lin, Y.; Duan, H.; Dong, D. Green Chem. 2010, 12, 893.   DOI
14 Rong, L.; Han, H; Jiang H; Tu S. Synth. Commun. 2008, 38, 3530.   DOI
15 Yamawaki, J.; Ando, T. Chem. Lett. 1979, 755.
16 Clark, J. H. Chem. Rev. 1980, 80, 429.   DOI
17 Wang, X. S.; Zhang, M. M.; Li, Q.; Yao, C. S.; Tu, S. J. Synth. Commun. 2008, 38, 1896.   DOI
18 Blass, B. E. Tetrahedron 2002, 58, 9302.
19 Schmittling, E. A.; Sawyer, J. S. Tetrahedron Lett. 1991, 32, 7207.   DOI
20 Basu, B.; Das, P.; Das, S. Curr. Org. Chem. 2008, 12, 141.   DOI
21 Lakowicz, J. R. Principles of Fluorescence Spectroscopy, 2nd ed.; Kluwer Academic/ Plenum Publishers: New York, 1999.
22 Demas, J. N.; Grosby, G. A. J. Phys. Chem. 1971, 75, 991.   DOI
23 Oshima, J.; Yoshihara, T.; Tobita, S. Chem. Phys. Lett. 2006, 423, 306.   DOI
24 Xue, D.; Chen, Y. C.; Cui, X.; Wang, Q.W.; Zhu, J.; Deng, J. G. J. Org. Chem. 2005, 70, 3584   DOI
25 Sandhu, Suresh; Jagir, S. Green Chem. Lett. and Rev. 2009, 2, 189   DOI
26 Mukhopadhyay, C.; Datta, A. Synth. Commun. 2008, 38, 2103.   DOI
27 Sepiol, J.; Milart, P. Tetrahedron 1985, 41, 5261.   DOI
28 Dumur, F.; Gautier, N.; Gallego-Planas, N.; Sahin, Y.; Levillain, E.; Mercier, N.; Hudhomme, P. J. Org. Chem. 2004, 69, 2164.   DOI
29 Depaemelaere, S.; De Schryver, F. C.; Verhoeven, J. W. J. Phys. Chem. A 1998, 102, 2109.   DOI
30 Xiao, Y.; Qian, X. H. Tetrahedron Lett. 2003, 44, 2087.   DOI
31 Griffiths, J.; Lockwood, M.; Roozpeikar, B. J. Chem. Soc. Perkin Trans. 2 1977, 1608.
32 Fox, M. A.; Chanon, M. Eds. Photoinduced Electron Transfer 1988.
33 Kurreck, H.; Huber, M. Angew. Chem. Int. Ed. 1995, 34, 849.   DOI
34 Prasad, P. N.; Williams, D. J. Introduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: NewYork, 1991.
35 Nalwa, H. S. Adv. Mater. 1993, 5, 341.   DOI
36 Long, N. J. Angew. Chem. Int. Ed. 1995, 34, 21.   DOI   ScienceOn
37 Wong, M. S.; Bosshard, C.; Pan, F.; Gunter, P. Adv. Mater. 1996, 8, 677.   DOI
38 Metzger, R. M.; Panetta, C. New. J. Chem. 1991, 15, 209.
39 Launay, J. P.; Ferry, D. K. Molecular Electronics In Granular Nanoelectronics; Plenum Press: New York, 1991.
40 Petty, M. C.; Bryce, M. R.; Bloor, D. Introduction to Molecular Electronics; Oxford University Press: New York, 1995.