SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP
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 th...
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| Autores principales: | , , |
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| Lenguaje: | English |
| Publicado: |
Sociedad Chilena de Química
2018
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| Materias: | |
| Acceso en línea: | http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072018000203954 |
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| Sumario: | 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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