A novel access to 2-aminofuranones via cyclization of functionalized γ-hydroxy-α,β-butenoates derived from N-hydroxybenzotriazole esters of α-hydroxy acids

Athanasellis, G; Detsi, A; Prousis, K; Igglessi-Markopoulou, O; Markopoulos, J

dc.contributor.author	Athanasellis, G	en
dc.contributor.author	Detsi, A	en
dc.contributor.author	Prousis, K	en
dc.contributor.author	Igglessi-Markopoulou, O	en
dc.contributor.author	Markopoulos, J	en
dc.date.accessioned	2014-03-01T01:18:33Z
dc.date.available	2014-03-01T01:18:33Z
dc.date.issued	2003	en
dc.identifier.issn	00397881	en
dc.identifier.uri	https://dspace.lib.ntua.gr/xmlui/handle/123456789/15077
dc.subject	Acylations	en
dc.subject	Alkenes	en
dc.subject	Carboxylic acids	en
dc.subject	Furans	en
dc.subject	Heterocycles	en
dc.subject	Lactones	en
dc.subject.other	Aromatic compounds	en
dc.subject.other	Carboxylic acids	en
dc.subject.other	Furan resins	en
dc.subject.other	Substitution reactions	en
dc.subject.other	Cyclization	en
dc.subject.other	Synthesis (chemical)	en
dc.subject.other	acetic acid derivative	en
dc.subject.other	acid	en
dc.subject.other	ester derivative	en
dc.subject.other	furanone derivative	en
dc.subject.other	glycolic acid	en
dc.subject.other	imide	en
dc.subject.other	malononitrile	en
dc.subject.other	n hydroxynebzotriazole	en
dc.subject.other	n hydroxysuccinimide	en
dc.subject.other	triazole derivative	en
dc.subject.other	unclassified drug	en
dc.subject.other	article	en
dc.subject.other	chemical modification	en
dc.subject.other	chemical reaction	en
dc.subject.other	cyclization	en
dc.subject.other	measurement	en
dc.subject.other	optical rotation	en
dc.title	A novel access to 2-aminofuranones via cyclization of functionalized γ-hydroxy-α,β-butenoates derived from N-hydroxybenzotriazole esters of α-hydroxy acids	en
heal.type	journalArticle	en
heal.identifier.primary	10.1055/s-2003-41040	en
heal.identifier.secondary	http://dx.doi.org/10.1055/s-2003-41040	en
heal.publicationDate	2003	en
heal.abstract	The reaction between the N-hydroxybenzotriazole esters of substituted glycolic acids and alkyl cyanoacetates or malononitrile leads to the synthesis of γ-hydroxy-functionalized butenoates which are cyclized under mild conditions to the corresponding 2-amino-3,5-disubstituted-4-furanones. That the products are optically active is confirmed by measurements of their optical rotations. On the other hand, replacement of N-hydroxybenzotriazole by N-hydroxysuccinimide might lead to by-products depending on the functionalized glycolic acid used.	en
heal.journalName	Synthesis	en
dc.identifier.doi	10.1055/s-2003-41040	en
dc.identifier.issue	13	en
dc.identifier.spage	2015	en
dc.identifier.epage	2022	en