Abstract
More efficient, cost effective and metal free DHP/TMSCl system for one pot reductive amination of aldehydes was developed. The method allows the efficient one pot synthesis of structurally diverse amines with Hantzsch ester as the hydrogen source in the presence of trimethylsilyl chloride as a catalyst in high to quantitative yields under mild conditions.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
S.J. Connon, Org. Biomol. Chem. (2007) 3407.
T. Henkel, R.M. Brunne, H. Mueller, F. Reichel, Angew. Chem. Int. Ed. 38 (1999) 643.
K.W. Henderson, W.J. Kerr, J.H. Moir, Chem. Commun. (2000) 479.
V. Gotor-Fernandez, P. Fernandez-Torres, V. Gotor, Tetrahedron Asy. 17 (2006) 2558.
M.F.A. Adamo, V.K. Aggarwal, M.A. Sage, J. Am. Chem. Soc. 122 (2000) 8317.
J.W. Nieuwenhuijzen, R.F.P. Grimbergen, C. Koopman, R.M. Kellogg, T.R. Vries, E. Van Echten, B. Kaptein, L.A. Hulshof, Q.B. Broxterman, Angew. Chem. Int. Ed. 41 (2002) 4281.
T. Suwa, I. Shibata, K. Nishino, A. Baba, Org. Lett. 1 (1999) 1579
C.F. Lane, Synthesis (1975) 135 and references cited therein
H. Firouzabadi, N. Iranpoor, H. Alinezhad, Bull. Chem. Soc. Jpn. 76 (2003) 143
H. Firouzabadi, N. Iranpoor, H. Alinezhad, Synth. Commun. 32 (2002) 3575
I. Shibata, T. Moriuchi Kawakami, D. Tanizawa, T. Suwa, E. Sugiyama, H. Matsuda, A. Baba, J. Org. Chem. 63 (1998) 383
R. Apodaca, W. Xiao, Org. Lett. 3 (2001) 1745.
T. Gross, A.M. Seayad, M. Ahmad, M. Beller, Org. Lett. 4 (2002) 2055
P.S. Reddy, S. Kanjilal, S. Sunitha, R.B.N. Prasad, Tetrahedron Lett. 48 (2007) 8807
H. Kato, I. Shibata, Y. Yasaka, S. Tsunoi, M. Yasuda, A. Baba, Chem. Commun. (2006) 4189
S. Hoffmann, M. Nicoletti, B. List, J. Am. Chem. Soc. 128 (2006) 13074
D. Menche, J. Hassfeld, J.J. Li, G. Menche, A. Ritter, S. Rudolph, Org. Lett. 8 (2006) 741
H. Firouzabadi, B. Zeynizadeh, Bull. Chem. Soc. Jpn. 70 (1997) 55
H. Firouzabadi, M. Adibi, Phosphorous, Sulfur and Silicon 142 (1998) 125
C. Salmi, C. Loncle, Y. Letourneux, J.M. Brunel, Tetrahedron 64 (2008) 4453
R.Y. Lai, C.I. Lee, S.T. Liu, Tetrahedron 64 (2008) 1213
T. Mizuta, S. Sakaguchi, Y. Ishii, J. Org. Chem. 70 (2005) 2195
M.R. Saidi, R. Stan Brown, A. Ziyaei-Halimjani, J. Iran. Chem. Soc. 4 (2007) 194
H. Firouzabadi, N. Iranpoor, H. Alinezhad, J. Iran. Chem. Soc. 6 (2009) 177.
M.A. Zolfigol, M. Mokhlesi, J. Iran. Chem. Soc. 5 (2008) 91
A. Saini, S. Kumar, J. Sandhu, J. Sci. Ind. Res. 67 (2008) 95
J.-J. Xia, G.-W. Wang, Synthesis (2005) 2379.
P.T. Franke, R.L. Johansen, S. Bertelsen, K.A. Jorøgensen, Chem. Asian J. 3 (2008) 216 and references cited therein
S.G. Ouellet, A.M. Walji, D.W.C. Macmillan, Acc. Chem. Res. 40 (2007) 1327 and references cited therein
T. Itoh, K. Nagata, A. Kurihara, M. Miyazaki, A. Ohsawa, Tetrahedron Lett. 43 (2002) 3105
D. Menche, J. Hassfeld, J. Li, G. Menche, A. Ritter, S. Rudolph, Org. Lett. 8 (2006) 741
R. Kadyrov, T.H. Riermeier, Angew. Chem., Int. Ed. 42 (2003) 5472.
N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei, M.R. Saidi, J. Org. Chem. 71 (2006) 3634
N. Azizi, L. Torkiyan, M.R. Saidi, Org. Lett. 8 (2006) 2079
N. Azizi, M.R. Saidi, Org. Lett. 7 (2005) 3649
N. Azizi, M.R. Saidi, Tetrahedron 63 (2007) 888
N. Azizi, M.R. Saidi, Organomet. 23 (2004) 1457
N. Azizi, A. Khajeh Amiri, M. Bolourtchian, M.R. Saidi, J. Iran. Chem. Soc. 6 (2009) 749
N. Azizi, E. Akbari, M.R. Saidi, J. Iran. Chem. Soc. 6 (2009) 165.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Azizi, N., Khajeh Amiri, A.R., Ghafuri, H. et al. Highly chemoselective reductive amination by one pot reaction of aldehydes, amines and Dihydropyridine Catalyzed by TMSCl. JICS 7, 428–431 (2010). https://doi.org/10.1007/BF03246028
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF03246028