Journal
JOURNAL OF THE CHILEAN CHEMICAL SOCIETY
Volume 63, Issue 2, Pages 3954-3957Publisher
SOC CHILENA QUIMICA
DOI: 10.4067/s0717-97072018000203954
Keywords
hexahydropyrimidine; Mannich bases; hydrogen bonding; conformational preference
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Funding
- Direccion de Investigaciones, Bogota (DIB), at the National University of Colombia [28427]
- Direccion de Investigaciones, Bogota (DIB), at the National University of Colombia (QUIPU) [201010023412]
- COLCIENCIAS
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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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