Nine heterocyclic zwitterionic boronate esters derived from carbonylphenylboronic acids and amino-diols are described. Compounds were prepared by direct condensation reaction between 3-or 4-formyl/acetylphenylboronic acids with 2-amino-2-methyl-1,3-propanediol (1a-1d) or serinol (2-amino-1,3-propanediol) (1e-1h). Compound 2e was obtained by reaction between 4-formylphenylboronic acid and serinol using a solvent mixture methanol/acetone, an aldol condensation reaction was observed. All compounds were characterized by common spectroscopic techniques such as FT-IR, mass spectrometry, and multinuclear1H, 13 C and 11B NMR spectroscopy. 11B NMR spectra showed signals between δ = 1.9 to 7.3 ppm for all compounds, indicating a tetracoordinated environment for the boron atoms in solution. X-ray diffraction analysis showed that boronates are contained in six-membered heterocycles, which have a chair conformation with-OH and-NH3 + substituents in syn disposition. The formation of channels in the crystal lattice that are filled with water and supported by hydrogen bonding interactions is noteworthy.
CITATION STYLE
León-Negrete, A., Villamil-Ramos, R., Sánchez-Portillo, P., González-Hernández, A., & Barba, V. (2022). Six-Membered Heterocyclic Boronate Esters. Synthesis and Structural Analysis. Journal of the Mexican Chemical Society, 66(4), 421–432. https://doi.org/10.29356/jmcs.v66i4.1718
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