4-AMINOPIPERIDINE BASED NEW AMINO-s-TRIAZINES AS POTENTIAL DENDRITIC BUILIDING-BLOCKS
Keywords:
4-aminopiperidine, SN2-Ar amination, dendritic cores, melaminesAbstract
Starting from commercial 4-aminopiperidine, three new amino-s-triazines, seen as potential dendritic building-blocks, were synthesised by chemoselective SN2-Ar amination of cyanuric chloride. A three steps synthetic sequence, (i) Boc-chemoselective N-protection of 4-aminopiperidine ® (ii) amination of cyanuric chloride ® (iii) deprotection, yielded a novel potential dendritic central unit, 2,4,6-tris[(piperidin-4-yl)amino]-s-triazine.
References
a) W. Zhang, E.E. Simanek, Org. Lett., 2000, 2, 843; b) M. B. Steffensen, E.E. Simanek, Angew. Chem. Int. Ed., 2004, 43, 5178; c) E. Hollink, E.E. Simanek, Org. Lett., 2006, 8, 2293; d) H. Crampton, E. Hollink, L.M. Perez, E.E. Simanek, New J. Chem., 2007, 31, 1283; e) A. Chouai, E.E. Simanek, J. Org. Chem., 2008, 73, 2357; f) J. Lim, E.E. Simanek, Org. Lett., 2008, 10, 201; g) A.E. Enciso, F. Ramirez-Crescencio, M. Zeiser, R. Redón, E.E. Simanek, Polym. Chem., 2015, 6, 5219; h) R.S. Sreeperumbuduru, Z.M. Abid, K.M. Claunch, H.-H. Chen, S.M. McGillivray, E.E. Simanek, RSC Adv., 2016, 6, 8806.
a) A. Chouai, V.J. Venditto, E.E. Simanek, Org. Synth., 2009, 86, 141; b) A. Chouai, V.J. Venditto, E.E. Simanek, Org. Synth., 2009, 86, 151.
a) F. Popa, I. Simioanca, M. Pintea, M. Fazekas, L. Gratecap, C. Berghian, C. Batiu, M. Darabantu, Studia UBB Chemia, 2008, LIII(4), 5; b) F. Popa, P. Lameiras, E. Henon, O. Moldovan, A. Martinez, C. Batiu, Y. Ramondenc, M. Darabantu, Can. J. Chem., 2011, 89, 1207; c) F. Popa, P. Lameiras, O. Moldovan, M. Tomoaia-Cotisel, E. Henon, A. Martinez, C. Sacalis, A. Mocanu, Y. Ramondenc, M. Darabantu, Tetrahedron, 2012, 68, 8945; d) O. Moldovan, P. Lameiras, I. Nagy, T. Opruta, F. Popa, C. Antheaume, Y. Ramondenc, M. Darabantu, Tetrahedron, 2013, 69, 2199.
a) X. Chen, P. Zhan, C. Pannecouque, J. Balzarini, E. De Clercq, X. Liu, Eur. J. Med. Chem., 2012, 51, 60; b) X. Chen, P. Zhan, Z. Cheng, C. Meng, S. Shao, C. Pannecouque, E. De Clercq, X. Liu, Bioorg. and Med. Chem., 2012, 20, 3856.
a) T. Drakenberg, S. Forsen, Chem. Commun., 1971, 21, 1404; b) S.S. Mirvish, P. Gannett, D.M. Babcook, D. Williamson, S.C. Chen, D.D. Weisenburger, J. Agric. Food Chem., 1991, 39, 1205; c) I. Willner, J. Rosengaus, Y. J. Eichen, Phys. Org. Chem., 1993, 6, 29; d) A.R. Katritzky, I. Ghiviriga, D.C. Oniciu, A. Barkock, J. Chem. Soc., Perkin Trans. 2, 1995, 4, 785; e) A.R. Katritzky, I. Ghiviriga, P.G. Steel, D.C. Oniciu, J. Chem. Soc., Perkin Trans. 2, 1996, 3, 443; f) P. Amm, N. Platzer, J. Guilhem, J.P. Bouchet, J.P. Volland, Magn. Reson. Chem., 1998, 36, 587; g) H.E. Birkett, R.K. Harris, P. Hodgkinson, K. Carr, M.H. Charlton, J.C. Cherryman, A.M. Chippendale, R.P. Glover, Magn. Reson. Chem., 2000, 38, 504; h) M. Amm, N. Platzer, J.P. Bouchet, J.P. Volland, Magn. Reson. Chem., 2001, 39, 77; i) I. Ghiviriga, D.C. Oniciu, Chem. Commun., 2002, 22, 2718; j) H.E. Birkett, J.C. Cherryman, A.M. Chippendale, J.O.S. Evans, R.K. Harris, M. James, I.J. King, G. Mc Pherson, Magn. Reson. Chem., 2003, 41, 324.
a) F. Friebolin, Basic one- and two-dimensional NMR spectroscopy, VCH Verlagsgesellschaft: Weinheim, New York, 1991, p. 93, 263-291; b) E.L. Eliel, H.S. Wilen, Stereochemistry of the Organic Compounds, John Wiley & Sons, New York, 1994, p. 642, 1191, http://www.sigmaaldrich.com/Graphics/COfAInfo/SigmaSAPQM/SPEC/64/640042/640042-BULK_______ALDRICH__.pdf.
a) F. Himmelsbach, G. Dahmann, T. von Ruden, T. Metz (Dr. Karl Thomas GmbH) 1998, US Pat. US5821240A1, Mar.5, 1997 / Oct.13, 1998, App. No. US 08/811,907; b) F. Himmelsbach, G. Dahmann, T. von Ruden, T. Metz (Dr. Karl Thomas GmbH) 1999, US Pat. US5977102A1, Mar.5, 1997 / Nov.2, 1999, App. No. US 08/812,002; c) D. Xiao, Y. Zhu, Y. Hu, H. Wang, Y. Liu, J. Li, D. Sun, Z. Wang, Y. Wei, Z. Wang, G. Tang, L. Jing (Centaurus Biopharma Co.,Ltd.) 2012, WO2012/103806A1, Jan.31, 2012/Aug.9, 2012. App. No. PCT/CN2012/070800.
a) M.B. Steffensen, E.E. Simanek, Org. Lett., 2003, 5, 2359; b) K.X. Moreno, E.E. Simanek, Tetrahedron Lett., 2008, 49, 1152; c) X.K. Moreno, E.E. Simanek, Macromolecules, 2008, 41, 4108; d) M.A. Mintzer, L.M. Perez, E.E. Simanek, Tetrahedron Lett., 2010, 51, 1631; e) E.E. Simanek, H. Abdou, S. Lalwani, J. Lim, M. Mintzer, V.J. Venditto, B. Vittur, Proc. R. Soc. A., 2010, 466, 1445.
H.K. Hall, J. Am. Chem. Soc., 1957, 79, 5441.
For the conformational analysis of cyclohexylamine (aminocyclohexane) by means of (VT) 1H-, 13C- or 15N-NMR and computational methods see a) H. Booth, M. L. Jozefowicz, J. Chem. Soc. Perkin 2, 1976, 895; b) H. –J. Schneider, V. Hoppen, J. Org. Chem., 1978, 43, 3866; c) G. W. Buchanan, V.L. Webb, Tetrahedron Lett., 1983, 24, 4519.
See for example a) J.T. Thurston, J.R. Dudley, D.W. Kaiser, I. Hechenbleikner, F.C. Schaefer, D. Holm-Hansen, J. Am. Chem. Soc., 1951, 73, 2981; b) K.N. Sarmah, N.K. Sarmah, K.B. Kurmi, T.V. Patel, Adv. Appl. Sci. Res., 2012, 3, 459.
a) M. Fazekas, M. Pintea, P. Lameiras, A. Lesur, C. Berghian, I. Silaghi-Dumitrescu, N. Plé, M. Darabantu, Eur. J. Org. Chem., 2008, 14, 2473; b) O. Moldovan, P. Lameiras, E. Hénon, F. Popa, A. Martinez, D. Harakat, C. Sacalis, Y. Ramondenc, M. Darabantu, Centr. Eur. J. Chem., 2012, 10, 1119; c) O. Moldovan, I. Nagy, P. Lameiras, C. Antheaume, C. Sacalis, M. Darabantu, Tetrahedron: Asymmetry, 2015, 26, 683; d) C. Morar, G. Turdean, A. Bende, P. Lameiras, C. Antheaume, L. M. Muresan, M. Darabantu, Compt. Rend. Chim., 2016, http://dx.doi.org/10.1016/j.crci.2016.07.002.
For the relevance of this α-geminal anisochrony versus a carbamate group in anancomeric 1-Boc-4-NH2 piperidine, see the 1H-NMR analysis of flipping non-symmetrically N-substituted-N-Boc piperazines in J. Lim, G.M. Pavan, O. Annunziata, E.E. Simanek, J. Am. Chem.Soc., 2012, 134, 1942.
W.E. Stewart, T.H. Siddall, Chem. Rev., 1970, 70, 517.
a) J. Lim, E.E. Simanek, Mol. Pharm., 2005, 2, 273; b) M. Pintea, M. Fazekas, P. Lameiras, I. Cadis, C. Berghian, I. Silaghi-Dumitrescu, F. Popa, C. Bele, N. Plé, M. Darabantu, Tetrahedron, 2008, 64, 8851.
H. Kessler, Angew. Chem., Int. Ed. Engl., 1982, 21, 512.
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