Abstract
In a one-pot procedure, enolizable ketones reacted with aromatic aldehydes, acetyl chloride and acetonitrile at room temperature in the presence of Zr(HSO4)4/SiO2 to furnish the corresponding β-acetamido ketones in improved yields.
Similar content being viewed by others
References
J. Barluenga, A.L. Viado, E. Aguilar, S. Fustero, B. Olano, J. Org. Chem. 58 (1993) 5972.
D.P. Henderson, M.C. Shelton, I.C. Cotterill, E.J. Toone, J. Org. Chem. 62 (1997) 7910.
M. Uramoto, K. Kobinata, K. Isono, T. Higashijima, T. Miyazawa, E.E. Jenkins, J. McCloskey, A. Tetrahedron Lett. 21 (1980) 3395.
H.D. Dakin, R. West, J. Biol. Chem. 78 (1928) 745.
M.M. Reddy, B. Bhatia, J. Iqbal, Tetrahedron Lett. 36 (1995) 4877.
D. Bahulayan, S.K. Das, J. Iqbal, J. Org. Chem. 68 (2003) 5735.
A.T. Khan, L.H. Choudhury, T. Parvin, M. Asif Ali, Tetrahedron Lett. 47 (2006) 8137.
M.M. Khodaei, A.R. Khosropour, P. Fattahpour, Tetrahedron Lett. 46 (2005) 2105.
M.M. Heravi, L. Ranjbar, F. Derikvand, F. Bamoharram, Catal. Commun. 8 (2007) 289.
L. Nagarapu, S. Kantevari, V.N. Cheemalapati, S. Apuri, V. Kumari, J. Mol.Catal. A: Chem. 264 (2006) 22.
M.T. Maghsoodlou, A. Hassankhani, H.R. Shaterian, S.M. Habibi-Khorasani, E. Mosaddegh, Tetrahedron Lett. 48 (2007) 1729.
B. Das, M. Krishnaiah, K. Laxminarayana, K.R. Reddy, J. Mol. Catal. A: Chem. 270 (2007) 284.
A.T. Khan, T. Parvin, L.H. Choudhury, Tetrahedron 63 (2007) 5593.
E. Rafiee, F. Tork, M. Joshaghani, Bioorg. Med. Chem. Lett. 16 (2006) 1221.
M.M. Heravi, L. Ranjbar, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A:Chem. 271 (2007) 28.
E. Rafiee, F. Paknezhad, S. Shahebrahimi, M. Joshaghani, S. Eavani, S. Rashidzadeh, J. Mol. Catal. A: Chem. 282 (2008) 92.
E. Rafiee, F. Shahbazi, M. Joshaghani, F. Tork. J. Mol. Catal. A: Chem. 242 (2005) 129.
Z. Mirjafary, H. Saeidian, A. Sadeghi, F. Matloubi Moghaddam, Catal. Commun. 9 (2008) 299.
M. Heravi, L. Ranjbar, F. Derikvand, F.F. Bamoharram, J. Mol. Catal. A:Chem. 276 (2007) 226.
G. Pandey, R.P. Singh, A. Garg, V.K. Singh, Tetrahedron Lett. 46 (2005) 2137.
L. Nagarapu, R. Bantu, R. Puttireddy, Appl. Catal. A: Gen. 332 (2007) 307.
R.P. Bhat, V.P. Raje, V.M. Alexander, S.B. Patil, S.D. Samant, Tetrahedron Lett. 46 (2005) 4801.
R. Ghosh, S. Maiti, A. Chakraborty, S. Chakraborty, A. K. Mukherjee, Tetrahedron 62 (2006) 4059.
T.V. Yakaiah, B.P. Lingaiah, G. Venkat Reddy, B. Narsaiah, P. Shanthan Rao, ARKIVOC 13 (2007) 227.
S. Besoluk, M. Kucukislamoglu, M. Nebioglu, M. Zengin, M. Arslan, J. Iran. Chem. Soc. 5 (2008) 62.
F. Shirini, M.A. Zolfigol, A.-R. Abri, J. Iran. Chem. Soc. 5 (2008) 96.
A. Bamoniri, B.F. Mirjalili, M.A. Zolfigol, I. Mohammadpoor-Baltork, J. Iran. Chem. Soc. 4 (2007) 332.
K. Niknam, M.A. Zolfigol, T. Sadabadi, A. Nejati, J. Iran. Chem. Soc. 3 (2006) 318.
M.A. Zolfigol, M. Bagherzadeh, K. Niknam, F. Shirini, I. Mohammadpoor-Baltork, A. Ghorbani Choghamarani, M. Baghbanzadeh, J. Iran. Chem. Soc. 3 (2006) 73.
K. Niknam, M.A. Zolfigol, T. Sadabadi, J. Iran. Chem. Soc. 4 (2007) 199.
A. Bamoniri, M.A. Zolfigol, I. Mohammadpoor-Baltork, B.F. Mirjalili, J. Iran. Chem. Soc. 3 (2006) 85.
F. Shirini, M.A. Zolfigol, A. Safari,; I. Mohammadpoor-Baltork, B.F. Mirjalili, Tetrahedron Lett. 44 (2003) 7463.
B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, N. Sheikhan, J. Chin. Chem. Soc. 53 (2006) 955.
B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, M.A. Karimi-Zarchi, Z. Zaghaghi, M. Parvaideh, J. Iran. Chem. Soc. 4 (2007) 340.
F. Shirini, M.A. Zolfigol, P. Salehi, M. Abedini, Cur. Org. Chem. 12 (2008) 183.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mirjalili, B.F., Bamoniri, A., Karimi Zarchi, M.A. et al. Zr(HSO4)4/SiO2: An effective heterogeneous alternative for one-pot synthesis of β-acetamido ketones. JICS 7, 95–99 (2010). https://doi.org/10.1007/BF03245864
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF03245864