JOURNAL OF CHILEAN CHEMICAL SOCIETY

Vol 63 No 2 (2018): Journal of the Chilean Chemical Society
Original Research Papers

SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP

Augusto Rivera
Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química
Ingrid Miranda-Carvajal
Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química
Jaime Ríos-Motta
Universidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química
Published June 25, 2018
Keywords
  • hexahydropyrimidine,
  • Mannich bases,
  • hydrogen bonding,
  • conformational preference
How to Cite
Rivera, A., Miranda-Carvajal, I., & Ríos-Motta, J. (2018). SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP. Journal of the Chilean Chemical Society, 63(2). Retrieved from https://jcchems.com/index.php/JCCHEMS/article/view/678

Abstract

A series of 2,2’-(5-hydroxydihydropyrimidine-1,3(2H,4H)-diyl)bis-(methylene)-disubstitutedphenols was synthesized by using a Mannich-type reaction between 1,3-diaminopropan-2-ol, paraformaldehyde and substituted phenols. These previously unreported compounds were separated from the reaction mixture by column chromatography (CC) in highly pure form with a 29%-91% yield. The effect of intramolecular hydrogen bonding on the conformation of 5-hydroxyhexahydropyrimidines has been studied. Our results show that the presence of hydroxyl groups can strongly influence the stereoelectronic relationships in the six-membered heterocyclic ring.

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