Copyright (c) 2016 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Silica-Sulfuric Acid: Novel, Simple, Efficient and Reusable Catalyst for Hydration of Nitrile to Amide
Asian Journal of Chemistry,
Vol. 28 No. 10 (2016): Vol 28 Issue 10
Abstract
Silica-sulfuric acid efficiently catalyzes conversion of aliphatic, substituted aromatic and hetero aromatic nitriles to their corresponding amides in good to excellent yields under reflux condition. Products obtained were purified by column chromatography method and characterized by 1H NMR, 13C NMR and mass spectral analysis.
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References
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L. McMaster and F.B. Langreck, J. Am. Chem. Soc., 39, 103 (1917); doi:10.1021/ja02246a012.
N. Kornblum and S. Singaram, J. Org. Chem., 44, 4727 (1979); doi:10.1021/jo00393a063.
A.R. Katritzky, B. Pilarski and L. Urogdi, Synthesis, 949 (1989); doi:10.1055/s-1989-27441.
J.H. Kim, J. Britten and J. Chin, J. Am. Chem. Soc., 115, 3618 (1993); doi:10.1021/ja00062a027.
J. Chin and J.H. Kim, Angew. Chem. Int. Ed. Engl., 29, 523 (1990); doi:10.1002/anie.199005231.
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K. Yamaguchi, Y. Wang, H. Kobayashi and N. Mizuno, Chem. Lett., 41, 574 (2012); doi:10.1246/cl.2012.574.
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J. Mahatthananchai, A.M. Dumas and J.W. Bode, Angew. Chem. Int. Ed., 51, 10954 (2012); doi:10.1002/anie.201201787.
R. Balicki and L. Kaczmarek, Synth. Commun., 23, 3149 (1993); doi:10.1080/00397919308011173.
S. Cacchi, D. Misiti and F. La Torre, Synthesis, 243 (1980); doi:10.1055/s-1980-28985.
A. Solhy, A. Smahi, H. El Badaoui, B. Elaabar, A. Amoukal, A. Tikad, S. Sebti and D.J. Macquarrie, Tetrahedron Lett., 44, 4031 (2003); doi:10.1016/S0040-4039(03)00872-4.
N.V. Kaminskaia and N.M. Kostic, J. Chem. Soc., Dalton Trans., 3677 (1996); doi:10.1039/dt9960003677.
G.W. Kabalka, S.M. Deshpande, P.P. Wadgaonkar and N. Chatla, Synth. Commun., 20, 1445 (1990); doi:10.1080/00397919008052860.
A. Sharifi, F. Mohsenzadeh, M.M. Mojtahedi, M.R. Saidi and S. Balalaie, Synth. Commun., 31, 431 (2001); doi:10.1081/SCC-100000535.
F. Fagalde, N.L. de Katz and N. Katz, J. Coord. Chem., 55, 587 (2002); doi:10.1080/00958970290020892.
K. Manjula and M. Afzal Pasha, Synth. Commun., 37, 1545 (2007); doi:10.1080/00397910701230147.
C.G. Rao, Synth. Commun., 12, 177 (1982); doi:10.1080/00397918208063674.
C. Mukherjee, D.M. Zhu, E.R. Biehl, R.R. Parmar and L. Hua, Tetrahedron, 62, 6150 (2006); doi:10.1016/j.tet.2006.04.069.
S. Sebti, A. Rhihil, A. Saber and N. Hanafi, Tetrahedron Lett., 37, 6555 (1996); doi:10.1016/0040-4039(96)01399-8.
C. Sandeep, B. Padmashali and R.S. Kulkarni, Tetrahedron Lett., 54, 6411 (2013); doi:10.1016/j.tetlet.2013.09.033.
K.N. Venugopala and B.S. Jayashree, Indian J. Pharm. Sci., 70, 88 (2008); doi:10.4103/0250-474X.40338.
K.N. Venugopala, R. Govender, M.A. Khedr, R. Venugopala, B.E. Aldhubiab, S. Harsha and B. Odhav, Drug Des. Devel. Ther., 9, 911 (2015); doi:10.2147/DDDT.S73890.
K.N. Venugopala, M. Krishnappa, S.K. Nayak, B.K. Subrahmanya, J.P. Vaderapura, R.K. Chalannavar, R.M. Gleiser and B. Odhav, Eur. J. Med. Chem., 65, 295 (2013); doi:10.1016/j.ejmech.2013.04.061.
K.N. Venugopala, S.K. Nayak, R.M. Gleiser, M.E. Sanchez-Borzone, D.A. Garcia and B. Odhav, Chem. Biol. Drug Des., 88, 88 (2016); doi:10.1111/cbdd.12736.