Abstract
Tertiary, secondary, and benzylic alcohols react efficiently with nitriles in the presence of the catalyst calcium hydrogen sulfate, Ca(HSO4)2, to produce amides in high yields. In this study, a modified Ritter reaction using this solid acid catalyst is found to be an environmentally safe method for converting 2,6-bis(hydroxymethyl)-4-halo anisole into the corresponding diamides in CH3CN.
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References
H. Firouzabadi, A.A. Jafari, J. Iran. Chem. Soc. 2 (2005) 85.
F. Shirini, M.A. Zolfigol, P. Salehi, Curr. Org. Chem. 10 (2006) 2171.
K. Niknam, M.A. Zolfigol, T. Sadabadi, A. Nejati, J. Iran. Chem. Soc. 3 (2006) 318.
J.J. Ritter, P.P. Minieri, J. Am. Chem. Soc. 70 (1948) 4045
F.R. Benson, J.J. Ritter, J. Am. Chem. Soc. 71 (1949) 4128.
J.A. Sanguigni, R.J. Levins, Med. Chem. 7 (1964) 573.
A. Carcia Martinez, R. Martinez Alvarez, E. Teso Villar, A. Garcia Fraile, M. Hanach, L.R. Subramanian, Tetrahedron Lett. 30 (1989) 581.
D.H.R. Barton, P.D. Magnus, R.N. Young, J. Chem. Soc. Chem. Commun. 331 (1973)
D.H.R. Barton, P.D. Magnus, J.A. Garbarino, R.N. Young, J. Chem. Soc. Perkin Trans. 1 (1974) 2101.
B. Kumar, H. Kumar, N. Singh, Indian J. Chem. 30B (1991) 460.
H. Firouzabadi, A.R. Sardarian, H. Badparva, Synth. Commun. 24 (1994) 7601.
G.A. Olah, T. Yamato, S. Lyer, Mater Chem. Phys. 17 (1987) 21.
M. Mukhopadhyay, M.M. Reddy, G.C. Maikap, J. Iqbal, J. Org. Chem. 60 (1995) 2670.
M. Mukhopadhyay, J. Iqbal, J. Org. Chem. 62 (1997) 1843.
M.M. Lakouraj, B. Movassagh, J. Fasihi, Synth. Commun. 30 (2000) 821.
P. Salehi, M.M. Khodaei, M.A. Zolfigol, A. Keyvan, Synth. Commun. 31 (2001) 1947.
P. Salehi, A. Rostamian Motlagh, Synth. Commun. 30 (2000) 671.
H. Sharghi, K. Niknam, Iran. J. Chem. s Chem. Eng. 18 (1999) 36.
T. Nishiguchi, Ch. Kamio, J. Chem. Soc. Perkin Trans. 1 (1989) 707
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Niknam, K., Zolfigol, M.A. & Sadabadi, T. Ca(HSO4)2 mediated conversion of alcohols into N-substituted amides under heterogeneous conditions: A modified Ritter reaction. JICS 4, 199–204 (2007). https://doi.org/10.1007/BF03245967
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DOI: https://doi.org/10.1007/BF03245967