Cyclisation of Novel Amino Oxo Esters to Tetramic Acids - Density Functional Theory Study of the Reaction Mechanism

Detsi, A; Afantitis, A; Athanasellis, G; Markopoulos, J; Igglessi-Markopoulou, O; Skylaris, C-K

dc.contributor.author	Detsi, A	en
dc.contributor.author	Afantitis, A	en
dc.contributor.author	Athanasellis, G	en
dc.contributor.author	Markopoulos, J	en
dc.contributor.author	Igglessi-Markopoulou, O	en
dc.contributor.author	Skylaris, C-K	en
dc.date.accessioned	2014-03-01T01:18:48Z
dc.date.available	2014-03-01T01:18:48Z
dc.date.issued	2003	en
dc.identifier.issn	1434-193X	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/15210
dc.subject	Acylation	en
dc.subject	Cyclization	en
dc.subject	Density functional theory	en
dc.subject	Medicinal chemistry	en
dc.subject.classification	Chemistry, Organic	en
dc.subject.other	ester derivative	en
dc.subject.other	gamma methylamino beta oxo ester derivative	en
dc.subject.other	nitrogen	en
dc.subject.other	tetramic acid derivative	en
dc.subject.other	unclassified drug	en
dc.subject.other	urethan	en
dc.subject.other	acylation	en
dc.subject.other	article	en
dc.subject.other	calculation	en
dc.subject.other	cyclization	en
dc.subject.other	density functional theory	en
dc.subject.other	isomerism	en
dc.subject.other	nuclear magnetic resonance spectroscopy	en
dc.subject.other	precursor	en
dc.subject.other	reaction analysis	en
dc.subject.other	synthesis	en
dc.subject.other	theory	en
dc.title	Cyclisation of Novel Amino Oxo Esters to Tetramic Acids - Density Functional Theory Study of the Reaction Mechanism	en
heal.type	journalArticle	en
heal.identifier.primary	10.1002/ejoc.200300422	en
heal.identifier.secondary	http://dx.doi.org/10.1002/ejoc.200300422	en
heal.language	English	en
heal.publicationDate	2003	en
heal.abstract	The synthesis of novel N-urethane-protected gamma-methylamino-beta-oxo esters and their use as precursors for the preparation of N-methyltetramic acids is described. The presence of the bulky urethane protecting group on the nitrogen atom gives rise to rotational isomers detectable in the NMR spectra of the compounds, along with the keto/enol tautomerism. The mechanism of the cyclisation reaction of gamma-amino-beta-oxo esters to tetramic acids was studied theoretically by the B3LYP hybrid density functional method. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).	en
heal.publisher	WILEY-V C H VERLAG GMBH	en
heal.journalName	European Journal of Organic Chemistry	en
dc.identifier.doi	10.1002/ejoc.200300422	en
dc.identifier.isi	ISI:000187126800015	en
dc.identifier.issue	23	en
dc.identifier.spage	4593	en
dc.identifier.epage	4600	en