Amination-reduction reaction as simple protocol for potential boronic molecular receptors. Insight in supramolecular structure directed by weak interactions
Tóm tắt
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
Tài liệu tham khảo
T.D. James, M.D. Phillips, S. Shinkai, Boronic Acids in Saccharide Recognition (RSC Publishing, Cambridge, 2006) 48, 54–55
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
W. Tan, D. Zhang, D. Zhu, Bioorg. Med. Chem. Lett. 17, 2629 (2007)
D.G. Hall. (Ed.), Boronic Acids. Preparation, applications in organic synthesis and medicine (VCH, Weinheim, 2005)
A. Adamczyk-Woźniak, M.K. Cyrański, A. Żubrowska, A. Sporzyński, J. Organomet. Chem. 694, 3533 (2009)
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)
A. Adamczyk-Woźniak, I. Madura, A.H. Velders, A. Sporzyński, Tetrahedron Lett. 51, 6181 (2010)
A.P. Davis, Nature 464, 169 (2010)
A. Sporzyński, M. Lewandowski, P. Rogowska, M.K. Cyrański, Appl. Organometal. Chem. 19, 1202 (2005)
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)
P.J. Duggan, T.A. Houston, M.J. Kiefel, S.M. Levonis, B.D. Smith, M.L. Szydzik, Tetrahedron 64, 7122 (2008)
M. Lauer, H. Böhnke, R. Grotstollen, M. Salehnia, G. Wulff, Chem. Ber. 118, 246 (1985)
L. Zhu, Z. Zhong, E.V.J. Anslyn, J. Am. Chem. Soc. 127, 4260 (2005)
B.E. Collins, S. Sorey, A.E. Hargrove, S.H. Shabbir, V.M. Lynch, E.V.J. Anslyn, J. Org. Chem. 74, 4055 (2009)
L. Zhu, S.H. Shabbir, M. Gray, V.M. Lynch, S. Sorey, E.V.J. Anslyn, J. Am. Chem. Soc. 128, 1222 (2006)
M.C. Etter, Acc. Chem. Res. 23, 120 (1990)
M.C. Etter, J.C. MacDonald, J. Bernstein, Acta Crystallogr. B46, 256 (1990)
M.A. Spackman, P.G. Byrom, Chem. Phys. Lett. 267, 215 (1997)
M.A. Spackman, D. Jayatilaka, CrystEngComm. 11, 19 (2009)
J.J. McKinnon, D. Jayatilaka, M.A. Spackman, Chem. Commun. 3814 (2007)
V. Kopsky, D.B. Litvin, (Eds.), International Tables for Crystallography, Subperiodic groups (Kluwer Academic Publishers, Dordrecht, 2002) Vol. E
R.R. Haynes, H.R. Snyder, J. Org. Chem. 29, 3229 (1964)
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