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

Rivera, Augusto; Miranda-Carvajal, Ingrid; Ríos-Motta, Jaime

dc.creator	Rivera, Augusto
dc.creator	Miranda-Carvajal, Ingrid
dc.creator	Ríos-Motta, Jaime
dc.date	2018-06-25
dc.date.accessioned	2019-11-13T15:11:47Z
dc.date.available	2019-11-13T15:11:47Z
dc.identifier	http://www.jcchems.com/index.php/JCCHEMS/article/view/678
dc.identifier.uri	https://revistaschilenas.uchile.cl/handle/2250/112682
dc.description	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.	en-US
dc.format	application/pdf
dc.language	eng
dc.publisher	Sociedad Chilena de Química	en-US
dc.relation	http://www.jcchems.com/index.php/JCCHEMS/article/view/678/236
dc.rights	Copyright (c) 2018 Journal of the Chilean Chemical Society	en-US
dc.rights	https://creativecommons.org/licenses/by-nc-sa/4.0	en-US
dc.source	Journal of the Chilean Chemical Society; Vol 63 No 2 (2018): Journal of the Chilean Chemical Society	en-US
dc.source	0717-9707
dc.source	0717-9324
dc.subject	hexahydropyrimidine	en-US
dc.subject	Mannich bases	en-US
dc.subject	hydrogen bonding	en-US
dc.subject	conformational preference	en-US
dc.title	SYNTHESIS OF 5-HYDROXYDIHYDROPYRIMIDINE DERIVATIVES AND THE INFLUENCE OF INTRAMOLECULAR HYDROGEN BONDING ON THEIR NMR PROPERTIES AND CONFORMATIONAL PREFERENCES OF THE HYDROXYL GROUP	en-US
dc.type	info:eu-repo/semantics/article
dc.type	info:eu-repo/semantics/publishedVersion

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