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Journal

2012 | 10 | 4 | 1119-1136

Article title

New serinolic amino-s-triazines by chemoselective amination of cyanuric chloride and their (pro)diastereomerism in restricted rotational phenomena

Content

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Languages of publication

EN

Abstracts

EN
The highly chemoselective preparation of new elaborated N-unsymmetrically substituted chlorodiamino-s-triazines and melamines, seen as building-blocks for iterative synthesis, is reported. It consisted of amination of cyanuric chloride with commercial C-2-substituted 2-aminopropane-1,3-diols (“serinols”), playing the role as “open-chain” unit and enantiopure (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diols (“p-nitrophenylserinols”) based amino-1,3-dioxanes (“closed-chain” unit). Issued from the restricted rotation about C(s-triazine)-N(exocyclic) partial double bonds, seen as axes of (pro)diastereomerism, a global four-component rotational equilibrium involving the title compounds is discussed based on DFT computation and (VT) NMR data. Depending on π-deficiency of the s-triazine core, an (un)synchronised deblocking of the generated rotational diastereomers was observed. They are discussed as influence of intra-vs. intermolecular NH...OH (dynamic) interactions occurring in the “open-chain” unit and the anancomeric, axial vs. equatorial, amino-anchorage of the “closed-chain” unit. [...]

Publisher

Journal

Year

Volume

10

Issue

4

Pages

1119-1136

Physical description

Dates

published
1 - 8 - 2012
online
29 - 5 - 2012

Contributors

author
  • ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France
author
  • ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France
author
  • ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France
  • ICMR — LIS, UMR 6229, University of Reims Champagne-Ardenne, BP 1039, 51687, Reims, France
  • Department of Organic Chemistry, “Babes-Bolyai” University, 400028, Cluj-Napoca, Romania
  • IRCOF — LCOFH, UMR 6014 CNRS COBRA, University and INSA of Rouen, 76821, Mont Saint-Aignan Cedex, France
  • Department of Organic Chemistry, “Babes-Bolyai” University, 400028, Cluj-Napoca, Romania

References

  • [1] M. Fazekas, M. Pintea, P. Lameiras, A. Lesur, C. Berghian, I. Silaghi-Dumitrescu, N. Plé, M. Darabantu, Eur. J. Org. Chem. 14, 2473 (2008) http://dx.doi.org/10.1002/ejoc.200700847[Crossref]
  • [2] M. Pintea, M. Fazekas, P. Lameiras, I. Cadis, C. Berghian, I. Silaghi-Dumitrescu, F. Popa, C. Bele, N. Plé, M. Darabantu, Tetrahedron 64, 8851 (2008) http://dx.doi.org/10.1016/j.tet.2008.06.071[Crossref]
  • [3] M. Darabantu, M. Pintea, M. Fazekas, P. Lameiras, C. Berghian, I. Delhom, I. Silaghi-Dumitrescu, N. Plé, A. Turck, Letters in Organic Chemistry 3, 905 (2006) http://dx.doi.org/10.2174/157017806779467933[Crossref]
  • [4] M. Fazekas, M. Darabantu, M. Pintea, P. Lameiras, C. Bele, C. Berghian, N. Plé, Heterocyclic Commun. 12, 151 (2006) http://dx.doi.org/10.1515/HC.2006.12.2.151[Crossref]
  • [5] M. Pintea, M. Darabantu, M. Fazekas, P. Lameiras, C. Berghian, I. Delhom, C. Bele, N. Plé, Heterocyclic Commun. 12, 135 (2006) http://dx.doi.org/10.1515/HC.2006.12.2.135[Crossref]
  • [6] V. Lates, D. Gligor, M. Darabantu, L.M. Muresan, J. Appl. Electrochem. 37, 631 (2007) http://dx.doi.org/10.1007/s10800-007-9293-5[Crossref]
  • [7] C. Bele, M. Darabantu, C.T. Matea, M. Pintea, M. Fazekas, C. Berghian, Buletin USAMV-CN 61, 194 (2005)
  • [8] C. Bele, M. Darabantu, M. Muntean, M. Pintea, M. Fazekas, C. Berghian, D. Lazar, Buletin USAMV-CN 60, 1454 (2004)
  • [9] M. Darabantu, Curr. Org. Synth. 7, 120 (2010) http://dx.doi.org/10.2174/157017910790820300[Crossref]
  • [10] M. Darabantu, Curr. Org. Synth. 7, 235 (2010) http://dx.doi.org/10.2174/157017910791162986[Crossref]
  • [11] D.A. Tomalia, Aldrichimica Acta 37, 39 (2004)
  • [12] M.B. Steffensen, E.E. Simanek, Angew. Chem. Int. Ed. 43, 5178 (2004) http://dx.doi.org/10.1002/anie.200460031[Crossref]
  • [13] M.B. Steffensen, E. Hollink, F. Kuschel, M. Bauer, E.E. Simanek, J. Polym. Sci. Part A: Polymer Chemistry 44, 3411 (2006) http://dx.doi.org/10.1002/pola.21333[Crossref]
  • [14] H.L. Crampton, E.E. Simanek, Polym. Int. 56, 489 (2007) http://dx.doi.org/10.1002/pi.2230[Crossref]
  • [15] E.E. Simanek, H. Abdou, S. Lalwani, J. Lim, M. Mintzer, V. J. Venditto, B. Vittur, Proc. R. Soc. A 466, 1445, (2010) http://dx.doi.org/10.1098/rspa.2009.0108[Crossref]
  • [16] X.C. Moreno, E.E. Simanek, Macromolecules 41, 4108 (2008) http://dx.doi.org/10.1021/ma702143f[Crossref]
  • [17] T. Drakenberg, S. Forsen, Chem. Commun. 21, 140 (1971)
  • [18] S.S. Mirvish, P. Gannett, D.M. Babcook, D. Williamson, S.C. Chen, D.D. Weisenburger, J. Agric. Food Chem. 39, 1205 (1991) http://dx.doi.org/10.1021/jf00007a002[Crossref]
  • [19] I. Willner, J. Rosengaus, Y. Eichen, J. Phys. Org. Chem. 6, 29 (1993) http://dx.doi.org/10.1002/poc.610060106[Crossref]
  • [20] A.R. Katritzky, I. Ghiviriga, D.C. Oniciu, A. Barkock, J. Chem. Soc. Perkin Trans. 2.4, 785 (1995) [Crossref]
  • [21] A.R. Katritzky, I. Ghiviriga, P.G. Steel, D.C. Oniciu, J. Chem. Soc. Perkin Trans. 2.3, 443 (1996) [Crossref]
  • [22] I. Ghiviriga, D.C. Oniciu, Chem. Commun. 22, 2718 (2002) http://dx.doi.org/10.1039/b206811g[Crossref]
  • [23] M. Amm, N. Platzer, J. Guilhem, J.P. Bouchet, J.P. Volland, Magn. Reson. Chem. 36, 587 (1998) http://dx.doi.org/10.1002/(SICI)1097-458X(199808)36:8<587::AID-OMR347>3.0.CO;2-B[Crossref]
  • [24] M. Amm, N. Platzer, J.P. Bouchet, J.P. Volland, Magn. Reson. Chem. 39, 77 (2001) http://dx.doi.org/10.1002/1097-458X(200102)39:2<77::AID-MRC801>3.0.CO;2-H[Crossref]
  • [25] 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. 38, 504 (2000) http://dx.doi.org/10.1002/1097-458X(200007)38:7<504::AID-MRC710>3.0.CO;2-7[Crossref]
  • [26] 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. 41, 324 (2003) http://dx.doi.org/10.1002/mrc.1185[Crossref]
  • [27] M. Darabantu, C. Maiereanu, G. Plé, C. Berghian, C. Condamine, Y. Ramondenc, Heterocyclic Commun. 7, 593 (2001) http://dx.doi.org/10.1515/HC.2001.7.6.593[Crossref]
  • [28] M. Darabantu, G. Plé, S. Mager, C. Puscas, E. Cotora, Tetrahedron 53, 1909 (1997) http://dx.doi.org/10.1016/S0040-4020(96)01106-4[Crossref]
  • [29] M. Darabantu, S. Mager, G. Plé, C. Puscas, Heterocycles 41, 2327 (1995) http://dx.doi.org/10.3987/REV-95-470[Crossref]
  • [30] M. Darabantu, S. Mager, C. Puscas, M. Bogdan, E. Cotora, G. Plé, I. Bratu, Revue Roumaine de Chimie 39, 955 (1994) (In French)
  • [31] R.C. Galesworthy, R.M. Show, B.C. Smith, J. Chem. Soc. 1507 (1962)
  • [32] R.M. Show, P.J. Ward, J. Chem. Soc. 5446 (1965) [Crossref]
  • [33] B.I. Stepanov, G.I. Migachev, E.F. Ilina, Zh. Obshch. Khim. 37, 2140 (1967) (In Russian)
  • [34] R.M. Show, P.J. Ward, J. Chem. Soc. 12, 1431 (1968)
  • [35] G.I. Migachev, E.F. Ilina, B.I. Stepanov, Zh. Obsch. Khim. 38, 1370 (1968) (In Russian)
  • [36] R.M. Show, P.J. Ward, J. Chem. Soc. 6, 596 (1969)
  • [37] G. Boncic-Caricic, Z.D. Tadic, M.D. Muskatirovic, J. Serb. Chem. Soc. 59, 929 (1994)
  • [38] N.D. Reddy, A.J. Elias, N. Ashwani-Vij, J. Chem. Research (S) 9, 504 (1998) http://dx.doi.org/10.1039/a801596a[Crossref]
  • [39] J. Chem. Research (M) 2033 (1998)
  • [40] B. Kolesinska, Z.J. Kaminski, Tetrahedron 65, 3573 (2009) http://dx.doi.org/10.1016/j.tet.2009.03.017[Crossref]
  • [41] L.-L. Lai, L.-Y. Wang, C.-H. Lee, C.Y. Lin, K.-L. Cheng, Org. Lett. 8, 1541 (2006) http://dx.doi.org/10.1021/ol0531076[Crossref]
  • [42] L.-L. Lai, C.-H Lee, L.-Y Wang, K.L. Cheng, H.-F, J. Org. Chem. 73, 485 (2008) http://dx.doi.org/10.1021/jo701990w[Crossref]
  • [43] W. Zhang, E.E. Simanek, Org. Lett. 2, 843 (2000) http://dx.doi.org/10.1021/ol005585g[Crossref]
  • [44] W. Zhang, D.T. Nowlan, L.M. Thomson, M.W. Lackowski, E.E. Simanek, J. Am. Chem. Soc. 123, 8914, (2001) http://dx.doi.org/10.1021/ja0041369[Crossref]
  • [45] W. Zhang, E.E. Simanek, Tetrahedron Lett. 42, 5355, (2001) http://dx.doi.org/10.1016/S0040-4039(01)01007-3[Crossref]
  • [46] W. Zhang, S.O. Gonzalez, E.E. Simanek, Macromolecules 35, 9015 (2002) http://dx.doi.org/10.1021/ma021101f[Crossref]
  • [47] A.P. Umali, E.E. Simanek, Org. Lett. 5, 1245 (2003) http://dx.doi.org/10.1021/ol034161u[Crossref]
  • [48] W. Zhang, S.E. Tichy, L.M. Perez, C.G. Maria, P.A. Lindahl, E.E. Simanek, J. Am. Chem. Soc. 125, 5086 (2003) http://dx.doi.org/10.1021/ja0210906[Crossref]
  • [49] E.J. Acosta, Y. Deng, G.N. White, J.B. Dixon, K.J. Mc Innes, S.A. Senseman, A.S. Frantzen, E.E. Simanek, Chem. Mater. 15, 2903 (2003) http://dx.doi.org/10.1021/cm0302328[Crossref]
  • [50] A.P. Umali, L.H. Crampton, E.E. Simanek, J. Org. Chem. 72, 9866 (2007) http://dx.doi.org/10.1021/jo701320h[Crossref]
  • [51] S. Yooa, S. Yeua, R.L. Sherman, E.E. Simanek, D.F. Shantza, D.M.J. Ford, Membrane Sci. 334, 16 (2009) http://dx.doi.org/10.1016/j.memsci.2009.02.011[Crossref]
  • [52] S. Lalwani, V.J. Venditto, A. Chouai, E.G. Rivera, S. Shaunak, E.E. Simanek, Macromolecules 42, 3152 (2009) http://dx.doi.org/10.1021/ma802250c[Crossref]
  • [53] F. Popa, P. Lameiras, E. Henon, O. Moldovan, A. Martinez, C. Batiu, Y. Ramondenc, M. Darabantu, Can. J. Chem. 89, 1207 (2011) http://dx.doi.org/10.1139/v11-075[Crossref]
  • [54] E.L. Eliel, H.S. Wilen, Stereochemistry of the Organic Compounds (John Wiley & Sons, New York, Chichester, Brisbane, Toronto, Singapore, 1994) 221–239, 488–507, 678, 788, 1210
  • [55] M.J.O. Anteunis, D. Tavernier, F. Borremans, Heterocycles 4, 293 (1976) http://dx.doi.org/10.3987/R-1976-02-0293[Crossref]
  • [56] J. Lim, E.E. Simanek, Mol. Pharmaceutics 2, 273 (2005) http://dx.doi.org/10.1021/mp050030e[Crossref]
  • [57] H. Kessler, Angew. Chem. Int. Ed. Engl. 21, 512 (1982) http://dx.doi.org/10.1002/anie.198205121[Crossref]
  • [58] H. Friebolin, Basic One- and Two Dimensional NMR Spectroscopy (VCH Verlagsgesellschaft, VCH: Weinheim, New York, 1991) 53, 93, 131, 132, 263–291
  • [59] R.M. Silverstein, F.X. Webster, D.J. Kiemle, Identification spectrométrique de composes organiques, 2nd edition (De Boeck & Larcier s.a., Bruxelles, 2007) 150–155 (In French)
  • [60] H. Shanan-Atidi, R.H. Bar Eli, J. Phys. Chem. 74, 961 (1970) http://dx.doi.org/10.1021/j100699a054[Crossref]
  • [61] H.S. Gutowski, C.H. Holm, J. Chem. Phys. 25, 1228 (1956) http://dx.doi.org/10.1063/1.1743184[Crossref]
  • [62] C. Berghian, P. Lameiras, L. Toupet, E. Condamine, N. Plé, A. Turck, C. Maiereanu, M. Darabantu, Tetrahedron, 62, 7319 (2006) http://dx.doi.org/10.1016/j.tet.2006.05.031[Crossref]
  • [63] M. Darabantu, C. Maiereanu, I. Silaghi-Dumitrescu, L. Toupet, E. Condamine, Y. Ramondenc, C. Berghian, G. Plé, N. Plé, Eur. J. Org. Chem. 12, 2644 (2004) http://dx.doi.org/10.1002/ejoc.200300584[Crossref]

Document Type

Publication order reference

Identifiers

YADDA identifier

bwmeta1.element.-psjd-doi-10_2478_s11532-012-0015-4
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