Abstract
Silica gel has been found to be an efficient and reusable medium for the synthesis of diastereospecific functionalized piperidines in good to high yields by a one-pot three-component condensation of aldehyde, amine and β-ketoester under solvent-free conditions at room temperature. Using this environmentally benign, non-inflammable and non-toxic reaction medium, the non-chromatographic purification, reusability of the silica gel, and operational simplicity are the notable advantages of the present method. The procedure is applicable for large-scale synthesis of piperidines derivatives and represents a green synthetic protocol.
Graphical Abstract
Similar content being viewed by others
References
A. McKillop, D.W. Young, Synthesis 1979, 401 (1979)
J.H. Clark, A.P. Kybett, D.J. Macquarre, Supported Reagents: Preparation, Analysis, and Application (VCH, New York, 1992)
K. Smith (ed.), Solid Supports and Catalysts in Organic Synthesis (Ellis Horwood, Chichester, 1992)
J.H. Clark, Catalysis of Organic Reactions by Supported Inorganic reagents (VCH, New York, 1994)
R.S. Verma, Green Chem. 1, 43 (1999)
A. Corma, H. Gracia, Chem. Rev. 103, 4307 (2003)
M.J. Climent, A. Corma, S. Iborra, Chem. Rev. 111, 1072 (2011)
P.T. Anastas, C.J. Warner, Green Chemistry: Theory and Practice (Oxford University Press, Oxford, 1998)
J. Zhu, H. Bienaymé (eds.), Multicomponent Reactions, 1st edn. (Wiley, Weinheim, 2005)
I. Ugi, Pure Appl. Chem. 73, 187 (2001)
V. Nair, C. Rajesh, A.U. Vinod, S. Bindu, A.R. Sreekanth, J.S. Mathen, L. Balagopal, Acc. Chem. Res. 36, 899 (2003)
D.J. Ramón, M. Yus, Angew. Chem. Int. Ed. 44, 1602 (2005)
A. Dömling, Chem. Rev. 106, 17 (2006)
B.M. Trost, Angew. Chem. Int. Ed. 34, 259 (1995)
P.A. Wender, S.T. Handy, D.L. Wright, Chem. Ind. 84, 765 (1997)
M. Baumann, I.R. Baxendale, S.V. Ley, N. Nikbin, Beilstein J. Org. Chem. 7, 442 (2011)
A.D. Elbein, R. Molyneux, in Alkaloids, Chemical and Biological Perspectives, vol. 57, ed. by S.W. Pelletier (Wiley, New York, 1987)
D. O’Hagan, Nat. Prod. Rep. 17, 435 (2000)
J.W. Daly, T.F. Spande, H.M. Garraffo, J. Nat. Prod. 68, 1556 (2005)
S. Petit, J.P. Nallet, M. Guillard, J. Dreux, R. Chermat, M. Poncelet, C. Bulach, P. Simon, C. Fontaine, M. Barthelmebs, J.L. Imbs, Eur. J. Med. Chem. 26, 19 (1991)
Y. Zhou, V.E. Gregor, B.K. Ayida, G.C. Winters, Z. Sun, D. Murphy, G. Haley, D. Bailey, J.M. Froelich, S. Fish, S.E. Webber, T. Hermann, D. Wall, Bioorg. Med. Chem. Lett. 17, 1206 (2007)
H. Bin, A.M. Crider, J.P. Stables, Eur. J. Med. Chem. 36, 265 (2001)
J.C. Jaen, L.D. Wise, T.G. Heffner, T.A. Pugsley, L.T. Meltzer, J. Med. Chem. 31, 1621 (1988)
A.B. Beeler, R.S.V.S. Gadepalli, S. Steyn Jr, N. Castagnoli, J.M. Rimoldi, Bioorg. Med. Chem. 11, 5229 (2003)
J.A. Dekus, J.R. Epperson, P.S. Charles, A.C. Joseph, P. Deextraze, J. Qian-Cutrone, Q. Gao, B. Ma, B.R. Beno, G.K. Mattson, T.F. Molski, R.G. Krause, M.T. Taber, N.J. Lodge, R.J. Mattson, Bioorg. Med. Chem. Lett. 17, 3099 (2007)
S.L. Gwaltney II, S.J. O’Connor, L.T.J. Nelson, G.M. Sulivan, H. Imade, W. Wang, L. Hasrold, Q. Li, J. Cohen, W.-Z. Gu, S.K. Tahir, J. Bauch, K. Marsh, S.-C. Ng, D.J. Frost, H. Zhang, S. Muchmore, C.G. Jacob, V. Stoll, C. Hutchins, Bioorg. Med. Chem. Lett. 13, 1359 (2003)
K. Kamei, N. Maeda, R. Katswagi-Ogino, M. Koyamaa, M. Nakajima, T. Tatsuoka, T. Ohno, T. Inone, Bioorg. Med. Chem. Lett. 15, 2990 (2005)
J.P. Yevich, F.D. Yocca, Curr. Med. Chem. 4, 295 (1997)
Y. Yamanishi, H. Ogura, T. Kosasa, Tanpakushitsu Kakusan Koso 45, 1047 (2000)
S. Targum, J. Zboroaski, M. Henry, P. Schmitz, T. Sebree, B. Wallin, Eur. Neuropsychopharmacol. 5, 4 (1995)
A. Schotte, P.F.M. Janssen, W. Gommeren, W.H.M.L. Luyten, P. van Gompel, A.S. Lasage, K. De Loore, J.E. Leysen, Psychopharmacology 57, 124 (1996)
K. Takasu, N. Shindoh, H. Tokuyama, M. Ihara, Tetrahedron 62, 11900 (2006)
M. Sales, A.B. Charette, Org. Lett. 7, 5773 (2005)
S. Fustero, D. Jiménez, J. Moscardó, S. Catalán, C. del Pozo, Org. Lett. 9, 5283 (2007)
F.A. Davis, B. Chao, A. Rao, Org. Lett. 3, 3169 (2001)
T.P. Lebold, A.B. Leduc, M.A. Kerr, Org. Lett. 11, 3770 (2009)
M.S.R. Murty, K.R. Ram, J.S. Yadav, Tetrahedron Lett. 49, 1141 (2008)
R.M. Carballo, M.A. Ramírez, M.L. Rodríguez, V.S. Martín, J.I. Padrón, Org. Lett. 8, 3837 (2006)
A.P. Dobbs, S.J.J. Guesné, Synlett 2005, 2101 (2005)
M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem. 17, 625 (2009)
A.T. Khan, T. Parvin, L.H. Choudhury, J. Org. Chem. 73, 8398 (2008)
A.T. Khan, M. Lal, M.M. Khan, Tetrahedron Lett. 51, 4419 (2010)
P.A. Clarke, A.V. Zaytzev, A.C. Whitwood, Tetrahedron Lett. 48, 5209 (2007)
C. Mukhopadhyay, S. Rana, R.J. Butcher, A.M. Schmiedekamp, Tetrahedron Lett. 52, 5835 (2011)
S. Verma, S.L. Jain, B. Sain, Beilstein J. Org. Chem. 7, 1334 (2011)
S. Mishra, R. Ghosh, Tetrahedron Lett. 52, 2857 (2011)
R. Aeluri, M. Alla, V.R. Bommena, R. Murthy, N. Jain, Asian J. Org. Chem. 1, 71 (2012)
H.-J. Wang, L.-P. Mo, Z.-H. Zhang, ACS Comb. Sci. 13, 181 (2011)
G. Brahmachari, S. Das, Tetrahedron Lett. 53, 1479 (2012)
J.S. Ghomi, A. Ziarati, J. Iran. Chem. Soc. 10, 135 (2013)
M. Lashkari, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, S.S. Sajadikhah, R. Doostmohamadi, Synth. Commun. 43, 635 (2013)
R. Ramachandran, S. Jayanthi, Y.T. Jeong, Tetrahedron 68, 363 (2012)
F. Shi, W. Tan, R.-Y. Zhu, G.-J. Xing, S.-J. Tua, Adv. Synth. Catal. 355, 1605 (2013)
X. Li, Y. Zhao, H. Qu, Z. Mao, X. Lin, Chem. Commun. 49, 1401 (2013)
S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, M. Lashkari, J. Chem. Res. 36, 463 (2012)
A.K. Banerjee, M.S.L. Mimo, W.J.V. Vegas, Russ. Chem. Rev. 70, 971 (2001)
G. Spagnol, A. Rajca, S. Rajca, J. Org. Chem. 72, 1867 (2007)
Y. Matsushita, K. Sugamoto, Y. Kita, T. Matsui, Tetrahedron Lett. 38, 8709 (1997)
B.C. Ranu, U. Jana, A. Majee, Green Chem. 1, 33 (1999)
B.C. Ranu, A. Hajra, U. Jana, Synlett 2000, 75 (2000)
B.C. Ranu, A. Hajra, Tetrahedron Lett. 57, 4767 (2001)
B.C. Ranu, A. Hajra, S.S. Dey, Org. Process Res. Dev. 6, 817 (2002)
B.C. Ranu, A. Hajra, Green Chem. 4, 551 (2002)
B.C. Ranu, S.S. Dey, A. Hajra, Green Chem. 5, 44 (2003)
M. Rahman, D. Kundu, A. Hajra, A. Majee, Tetrahedron Lett. 51, 2896 (2010)
B.C. Ranu, A. Majee, A. Sarkar, J. Org. Chem. 63, 370 (1998)
P.J. Kropp, G.W. Breton, S.L. Craig, S.D. Crawford, Jr. W.F. Durland, J.E. Jones, III, J.S. Raleigh, J. Org. Chem. 60, 4146 (1995) and the references cited therein
Acknowledgments
A.H. and A.M. acknowledge the financial support from CSIR, Govt. of India (Grant No. 02(0168)/13/EMR-II). We are grateful to DST-FIST and UGC-SAP. A.K.B. and S.S. thank CSIR and UGC for their fellowships.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Das, S., Bagdi, A.K., Santra, S. et al. Solvent-free silica-promoted multicomponent condensation: synthesis of highly functionalized piperidines. Res Chem Intermed 41, 6749–6763 (2015). https://doi.org/10.1007/s11164-014-1774-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-014-1774-7