Abstract
An efficient method for the synthesis of highly functionalized piperidines via one-pot domino reaction of β-ketoesters, aromatic aldehydes, and aromatic amines was reported. This multicomponent coupling was catalyzed by TMSI in methanol at room temperature, giving desired substituted pyridines in moderate to good yields.
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References:
A.R. Pinder, Nat. Prod. Rep. 9, 491 (1992)
D. O’Hagan, Nat. Prod. Rep. 17, 435 (2000)
C. Viegas, J.V.S. Bolzani, M. Furlan, E.J. Barreiro, M.C.M. Young, D. Tomazela, M.N. Eberlin, J. Nat. Prod. 67, 908 (2004)
J.W. Daly, T.F. Spande, H.M. Garraffo, J. Nat. Prod. 68, 1556 (2005)
M.C. Desai, S.L. Lefkowitz, P.F. Thadeio, K.P. Longo, R.M. Srider, J. Med. Chem. 35, 4911 (1992)
P.A. Clarke, A.V. Zaytzev, A.C. Whitwood, Tetrahedron Lett. 48, 5209 (2007)
J.P. Yevich, F.D. Yocca, Curr. Med. Chem. 4, 295 (1997)
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, Psycholpharmacology 124, 57 (1996)
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)
M. Misra, S.K. Pandey, V.P. Pandey, J. Pandey, R. Tripathi, R.P. Tripathi, Bioorg. Med. Chem. 17, 625 (2009)
S.A. Khanum, V. Girish, S.S. Suparshwa, N.F. Khanum, Bioorg. Med. Chem. Lett. 19, 1887 (2009)
B. Ho, A.M. Crider, J.P. Stables, Eur. J. Med. Chem. 36, 265 (2001)
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)
P.E. Goss, M.A. Baker, J.P. Carver, J.W. Dennis, Clin. Cancer Res. 1, 935 (1995)
Y. Nishimura, T. Satoh, H. Adachi, S. Kondo, T. Takeuchi, M. Azetaka, H. Fukuyasu, Y. Iizuka, J. Med. Chem. 40, 2626 (1997)
O. Benkert, G. Gründer, H. Wetzel, Pharmacopsychiatry 25, 254 (1992)
G. Gründer, H. Wetzel, E. Hammes, O. Benkert, Psychopharmacology 111, 123 (1993)
D. Bravi, T.L. Davis, M.M. Mouradian, T.N. Chase, Mov. Disord. 8, 195 (1993)
J.D. Adams, M.L. Chang, L. Klaidman, Curr. Med. Chem. 8, 809 (2001)
M. Von Itzstein, W.Y. Wu, G.B. Kok, M.S. Pegg, J.C. Dyason, B. Jin, T.V. Phan, M.L. Smythe, H.F. White, S.W. Oliver, P.M. Colman, J.N. Varghese, D.M. Ryan, J.M. Woods, R.C. Bethell, V.J. Hothman, J.M. Camreon, C.R. Penn, Nature 363, 418 (1993)
C.U. Kim, W. Lew, M.A. Williams, H. Liu, L. Zhang, S. Swaminathan, N. Bischofberger, M.S. Chen, D.B. Mendel, C.Y. Tai, W.G. Laver, R.C. Stevens, J. Am. Chem. Soc. 119, 681 (1997)
P. Chand, P.L. Kotian, A. Dehghani, Y. El-Kattan, T.H. Lin, T.L. Hutchison, Y.S. Babu, S. Bantia, A.J. Elliott, J.A. Montgomery, J. Med. Chem. 44, 4379 (2001)
G.B. Karlsson, T.D. Butters, R.A.P. Dwek, F.M. Latt, J. Biol. Chem. 268, 570 (1993)
J.E. Groopman, Rev. Infect. Dis. 12, 93 (1990)
J.L. Treadway, P. Mendys, D.J. Hoover, Expert Opin. Invest. Drugs 10, 439 (2001)
G.S. Jacob, Curr. Opin. Struct. Biol. 5, 605 (1995)
C.C.A. Cariou, G.J. Clarkson, M.J. Shipman, Org. Chem. 73, 9762 (2008)
R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, T.A. Keating, Acc. Chem. Res. 29, 123 (1996)
L. Zhou, D.S. Bohle, H.F. Jiang, C.J. Li, Synlett 2009, 937 (2009)
C. Mukhopadhyay, P.K. Tapaswi, M.G.B. Drew, Tetrahedron Lett. 51, 3944 (2010)
K. Kumaravel, G. Vasuki, Curr. Org. Chem. 13, 1820 (2009)
S. Brauch, L. Gabriel, B. Westermann, Chem. Commun. 46, 3387 (2010)
B.M. Trost, Angew. Chem. Int. Ed. 34, 259 (1995)
S. Mohammadi, M. Abbasi, Res. Chem. Intermed. 41, 8877 (2015)
M. Zarei, S.S. Sajadikhah, Res. Chem. Intermed. 42, 7005 (2016)
S.S. Sajadikhah, N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, A. Beigbabaei, M. Lashkari, J. Chem. Res. 36, 463 (2012)
H.R. Shaterian, K. Azizi, J. Mol. Liq. 180, 187 (2013)
M. Abbasi, RSC Adv. 5, 67405 (2015)
C. Mukhopadhyay, S. Rana, R.J. Butcher, A.M. Schmiedekamp, Tetrahedron Lett. 52, 5835 (2011)
J. Aboonajmi, M.T. Maghsoodlou, N. Hazeri, M. Lashkari, M. Kangani, Res. Chem. Intermed. 41, 8057 (2015)
Z. Madanifar, M.T. Maghsoodlou, M. Kangani, N. Hazeri, Res. Chem. Intermed. 41, 9863 (2015)
A. Mulik, P. Hegade, D. Patil, G. Mulik, S. Salunkhe, M. Deshmukh, Res. Chem. Intermed. 43, 729 (2017)
S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, S.M. Habibi-Khorassani, A.C. Willis, Chin. Chem. Lett. 23, 569 (2012)
R. Bharti, T. Parvin, J. Heterocyclic Chem. 52, 1806 (2015)
G. Brahmachari, S. Das, Tetrahedron Lett. 53, 1479 (2012)
S. Mishra, R. Ghosh, Tetrahedron Lett. 52, 2857 (2011)
F.O. Chahkamali, M.R. Faghihi, M.T. Maghsoodlou, Res. Chem. Intermed. 42, 8109 (2016)
S. Khaksar, S.M. Vahdat, M. Alipour, C. R. Chimie 16, 1024 (2013)
B. Umamahesh, V. Sathesh, G. Ramachandran, M. Sathishkumar, K. Sathiyanarayanan, Catal. Lett. 142, 895 (2012)
M. Abbasi, S.M. Seyedi, H. Sadeghian, M. Akhbari, M. Enayaty, A. Shiri, Heterocycl. Commun. 22, 117 (2016)
M.R.M. Shafiee, B.H. Najafabadi, M.J. Ghashang, Chem. Res. 36, 336 (2012)
N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, J. Aboonajmi, S.S. Sajadikhah, J. Chin. Chem. Soc. 60, 355 (2013)
A. Sobhani-Nasab, A. Ziarati, M. Rahimi-Nasrabadi, M.R. Ganjali, A. Badiei, Res. Chem. Intermed. 43, 6155 (2017)
A. Javidan, A. Ziarati, J. Afaei-Ghomi, Ultrason. Sonochem. 21, 1150 (2014)
M.B. Gawande, V.D.B. Bonifácio, R.S. Varma, I.D. Nogueira, N. Bundaleski, C.A.A. Ghumman, O.M.N.D. Teodoro, P.S. Branco, Green Chem. 15, 1226 (2013)
A. Maleki, A.A. Jafari, S. Yousefi, J. Iran. Chem. Soc. 14, 1801 (2017)
M.A.E.A.A. El-Remaily, A.M. Abu-Dief, R.M. El-Khatib, Appl. Organometal. Chem. 30, 1022 (2016)
P. Kar, B.G. Mishra, S.R. Pradhan, J. Mol. Catal. A Chem. 387, 103 (2014)
H. Eshghi, A. Khojastehnezhad, F. Moeinpour, M. Bakavoli, S.M. Seyedi, M. Abbasi, RSC Adv. 4, 39782 (2014)
H. Eshghi, A. Khojastehnezhad, F. Moeinpour, S. Rezaeian, M. Bakavoli, M. Teymouri, A. Rostami, K. Haghbeen, Tetrahedron 71, 436 (2015)
R. Jahanshahi, B. Akhlaghinia, New J. Chem. 41, 7203 (2017)
A. Gupta, R. Kaur, D. Singh, K.K. Kapoor, Tetrahedron Lett. 58, 2583 (2017)
G.A. Olah, S.C. Narang, Tetrahedron 38, 2225 (1982)
S.Q. Yan, N. Ding, W. Zhang, P. Wang, Y.X. Li, M. Li, Carbohydr. Res. 354, 6 (2012)
Y.X. Chun, S.Q. Yan, X.P. Li, N. Ding, W. Zhang, P. Wang, M. Li, Y.X. Li, Tetrahedron Lett. 52, 6196 (2011)
S.Q. Yan, N. Ding, W. Zhang, P. Wang, Y.X. Li, M. Li, J. Carbohydr. Chem. 31, 571 (2012)
S.Q. Yan, W. Guo, W.S. Wang, W. Zhang, Chin. J. Org. Chem. 39, 1469 (2019)
S.Q. Yan, D.Q. Dong, C.W. Xie, W.S. Wang, Z.L. Wang, Chin. J. Org. Chem. 39, 2560 (2019)
S.Q. Yan, S.W. He, S.Y. Li, Z.Q. Hu, W. Zhang, Heterocycles 100, 547 (2020)
Acknowledgements
We gratefully acknowledge financial support from the National Natural Science Foundation of China (Grant No. 51604207, 51674183), the Natural Science Foundation of Hubei Province, China (Grant No. 2018CFB605), the Shandong Provincial Education Department, China (Grant No. J18KB083), the Qingchuang Talent Incubation Program from Colleges and universities in Shandong Province (Grant No. 2019) and the Funded by Ship Control Engineering and Intelligent Systems Engineering Technology Research Center of Shandong Province and Ship Motion Control and Systems Engineering Technology Research center of Weihai, China (Grant No. SSCC-2018-0001 and SSCC-2019-0005).
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Wu, L., Yan, S., Wang, W. et al. Multicomponent reaction for the synthesis of highly functionalized piperidine scaffolds catalyzed by TMSI. Res Chem Intermed 46, 4311–4322 (2020). https://doi.org/10.1007/s11164-020-04208-6
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DOI: https://doi.org/10.1007/s11164-020-04208-6