Abstract
The influence of hydroxyl groups on the β-phenylethylamine aromatic ring was studied during its reaction with non-enolizable aldehydes. Computational calculations established that the degree of hydroxylation generates differences in the activation patterns of the ring (different reaction pathways) and in the nucleophilicity of the nitrogen atoms (different reaction yields). Cyclic aminals, benzoxazinephanes, or tetrahydroisoquinolines were obtained in the reaction with formaldehyde, and Schiff’s bases or tetrahydroisoquinolines were produced in the reaction with other non-enolizable aldehydes. The product obtained depends on the degree of hydroxylation of the ring of the starting phenylethylamine.
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Acknowledgments
The authors wish to acknowledge the Universidad Nacional de Colombia for funding this study (DIB Research Project No. 18615). C.D.-O. thanks the Vicerrectoría Académica de la Universidad Nacional de Colombia for their fellowship support. Y.Q.-A. thanks COLCIENCIAS for their fellowship support.
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Quevedo, R., Díaz-Oviedo, C. & Quevedo-Acosta, Y. Role of hydroxyl groups on the aromatic ring in the reactivity and selectivity of the reaction of β-phenylethylamines with non-enolizable aldehydes. Res Chem Intermed 41, 9835–9843 (2015). https://doi.org/10.1007/s11164-015-1987-4
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DOI: https://doi.org/10.1007/s11164-015-1987-4