Synthesis of 5-hydroxydihydropyrimidine derivatives and the influence of intramolecular hydrogen bonding on their nmr properties and conformational preferences of the hydroxyl group

• Autores: Augusto Rivera U., Ingrid Miranda-Carvajal, Jaime Ríos-Motta
• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 63, Nº. 2, 2018, págs. 3954-3957
• Idioma: inglés
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• Resumen

  • 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.