Amination-reduction reaction as simple protocol for potential boronic molecular receptors. Insight in supramolecular structure directed by weak interactions

• Authors: Agnieszka Adamczyk-Woźniak , Izabela Madura , Alicja Pawełko , Andrzej Sporzyński , Anna Żubrowska , Jacek Żyła
• Languages of publication: EN

Abstracts

EN

The synthesis of the potential molecular receptors in the amination-reduction reaction has been investigated within the model system comprising (2-formylphenyl)boronic acid and morpholine. The 3-amine substituted benzoxaborole was identified to be the intermediate of the synthesis and the unsubstituted benzoxaborole as the by-product resulting from reduction of the starting material. The insight into the reactivity of the starting materials as well as the intermediate benzoxaborole enabled significant rise in the yield of 2-(aminomethyl) phenylboronic acids synthesis. The solid state structure of 2-(piperidylmethyl)phenylboronic acid has been re-determined, and the description of the molecule and the crystal is given. The supramolecular layer structure directed by the weak C-H…O and C-H…π interactions was identified and scrutinized based on the geometry and Hirshfeld surface analyses

Keywords

EN

Boronic acids; Benzoxaboroles; X-ray structure; Hirshfeld surface; Supramolecular structure

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2011
• Volume: 9
• Issue: 2
• Pages: 199-205

Dates

published

1 - 4 - 2011

online

17 - 2 - 2011

Contributors

author

Agnieszka Adamczyk-Woźniak

• Warsaw University of Technology

author

Izabela Madura

• Warsaw University of Technology

author

Alicja Pawełko

• Warsaw University of Technology

author

Andrzej Sporzyński

• Warsaw University of Technology

author

Anna Żubrowska

• Warsaw University of Technology

author

Jacek Żyła

• Warsaw University of Technology

References

• [1] T.D. James, M.D. Phillips, S. Shinkai, Boronic Acids in Saccharide Recognition (RSC Publishing, Cambridge, 2006) 48, 54–55
• [2] A. Sporzyński, A. Żubrowska, A. Adamczyk-Woźniak, In: V.I. Rybachenko (Ed.), Synthetic receptors in molecular recognition (Schidnyj wydawnyczyj dim, Donetsk, Ukraine, 2007) 51–87
• [3] W. Tan, D. Zhang, D. Zhu, Bioorg. Med. Chem. Lett. 17, 2629 (2007) http://dx.doi.org/10.1016/j.bmcl.2007.01.099[Crossref]
• [4] D.G. Hall. (Ed.), Boronic Acids. Preparation, applications in organic synthesis and medicine (VCH, Weinheim, 2005)
• [5] A. Adamczyk-Woźniak, M.K. Cyrański, A. Żubrowska, A. Sporzyński, J. Organomet. Chem. 694, 3533 (2009) http://dx.doi.org/10.1016/j.jorganchem.2009.07.022[Crossref]
• [6] A. Adamczyk-Woźniak, M.K. Cyrański, M. Jakubczyk, P. Klimentowska, A. Koll, J. Kołodziejczak, G. Pojmaj, A. Żubrowska, G.Z. Żukowska, A. Sporzyński, J. Phys. Chem. A 114, 2324 (2010) http://dx.doi.org/10.1021/jp9086283[Crossref]
• [7] A. Adamczyk-Woźniak, I. Madura, A.H. Velders, A. Sporzyński, Tetrahedron Lett. 51, 6181 (2010) http://dx.doi.org/10.1016/j.tetlet.2010.09.091[Crossref]
• [8] A.P. Davis, Nature 464, 169 (2010) http://dx.doi.org/10.1038/464169a[Crossref]
• [9] A. Sporzyński, M. Lewandowski, P. Rogowska, M.K. Cyrański, Appl. Organometal. Chem. 19, 1202 (2005) http://dx.doi.org/10.1002/aoc.991[Crossref]
• [10] A. Adamczyk-Woźniak, Z. Brzózka, M.K. Cyrański, A. Filipowicz-Szymańska, P. Klimentowska, A. Żubrowska, K. Żukowski, A. Sporzyński, Appl. Organometal. Chem. 22, 427 (2008) http://dx.doi.org/10.1002/aoc.1418[Crossref]
• [11] P.J. Duggan, T.A. Houston, M.J. Kiefel, S.M. Levonis, B.D. Smith, M.L. Szydzik, Tetrahedron 64, 7122 (2008) http://dx.doi.org/10.1016/j.tet.2008.05.052[Crossref]
• [12] M. Lauer, H. Böhnke, R. Grotstollen, M. Salehnia, G. Wulff, Chem. Ber. 118, 246 (1985) http://dx.doi.org/10.1002/cber.19851180124[Crossref]
• [13] L. Zhu, Z. Zhong, E.V.J. Anslyn, J. Am. Chem. Soc. 127, 4260 (2005) http://dx.doi.org/10.1021/ja0435945[Crossref]
• [14] B.E. Collins, S. Sorey, A.E. Hargrove, S.H. Shabbir, V.M. Lynch, E.V.J. Anslyn, J. Org. Chem. 74, 4055 (2009) http://dx.doi.org/10.1021/jo900187a[Crossref]
• [15] L. Zhu, S.H. Shabbir, M. Gray, V.M. Lynch, S. Sorey, E.V.J. Anslyn, J. Am. Chem. Soc. 128, 1222 (2006) http://dx.doi.org/10.1021/ja055817c[Crossref]
• [16] M.C. Etter, Acc. Chem. Res. 23, 120 (1990) http://dx.doi.org/10.1021/ar00172a005[Crossref]
• [17] M.C. Etter, J.C. MacDonald, J. Bernstein, Acta Crystallogr. B46, 256 (1990)
• [18] M.A. Spackman, P.G. Byrom, Chem. Phys. Lett. 267, 215 (1997) http://dx.doi.org/10.1016/S0009-2614(97)00100-0[Crossref]
• [19] M.A. Spackman, D. Jayatilaka, CrystEngComm. 11, 19 (2009) http://dx.doi.org/10.1039/b818330a[Crossref]
• [20] J.J. McKinnon, D. Jayatilaka, M.A. Spackman, Chem. Commun. 3814 (2007)
• [21] V. Kopsky, D.B. Litvin, (Eds.), International Tables for Crystallography, Subperiodic groups (Kluwer Academic Publishers, Dordrecht, 2002) Vol. E
• [22] R.R. Haynes, H.R. Snyder, J. Org. Chem. 29, 3229 (1964) http://dx.doi.org/10.1021/jo01034a025[Crossref]
• [23] S.K. Wolff, D.J. Grimwood, J.J. McKinnon, D. Jayatilaka, M.A. Spackman, CrystalExplorer 2.1 (University of Western Australia, Perth, 2007) http://hirshfeldsurface.net/CrystalExplorer

Identifiers

DOI

10.2478/s11532-010-0142-8