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Novel short-step synthesis of functionalized γ-phenyl-β- hydroxybutenoates and their cyclization to 4-hydroxycoumarins via the N-hydroxybenzotriazole methodology

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dc.contributor.author Athanasellis, G en
dc.contributor.author Melagraki, G en
dc.contributor.author Chatzidakis, H en
dc.contributor.author Afantitis, A en
dc.contributor.author Detsi, A en
dc.contributor.author Igglessi-Markopoulou, O en
dc.contributor.author Markopoulos, J en
dc.date.accessioned 2014-03-01T01:21:09Z
dc.date.available 2014-03-01T01:21:09Z
dc.date.issued 2004 en
dc.identifier.issn 00397881 en
dc.identifier.uri https://dspace.lib.ntua.gr/xmlui/handle/123456789/16091
dc.subject Acylations en
dc.subject Coumarins en
dc.subject Heterocycles en
dc.subject N-hydroxybenzotriazole en
dc.subject Natural products en
dc.subject NMR spectroscopy en
dc.subject.other Acylation en
dc.subject.other Esters en
dc.subject.other Nuclear magnetic resonance en
dc.subject.other Spectroscopic analysis en
dc.subject.other C-acylation compounds en
dc.subject.other Methylene compounds en
dc.subject.other Salicylic acids en
dc.subject.other Title compounds en
dc.subject.other Synthesis (chemical) en
dc.subject.other 3 acetyl 4 hydroxy 6 methylcoumarin en
dc.subject.other 3 acetyl 4 hydroxy 8 methoxycoumarin en
dc.subject.other 3 acetyl 4 hydroxy 8 methylcoumarin en
dc.subject.other 3 acetyl 4 hydroxycoumarin en
dc.subject.other 3 acetyl 6 chloro 4 hydroxycoumarin en
dc.subject.other 3 benzoyl 4 hydroxycoumarin en
dc.subject.other 3 cyano 4 hydroxy 8 methoxycoumarin en
dc.subject.other 3 cyano 4 hydroxy 8 methylcoumarin en
dc.subject.other 3 cyano 4 hydroxycoumarin en
dc.subject.other 3 ethoxycarbonyl 4 hydroxy 6 methylcoumarin en
dc.subject.other 3 ethoxycarbonyl 4 hydroxy 8 methoxycoumarin en
dc.subject.other 3 ethoxycarbonyl 4 hydroxy 8 methylcoumarin en
dc.subject.other 3 ethoxycarbonyl 4 hydroxycoumarin en
dc.subject.other 4 hydroxy 3 methoxycarbonylcoumarin en
dc.subject.other 4 hydroxycoumarin derivative en
dc.subject.other 6 chloro 3 cyano 4 hydroxycoumarin en
dc.subject.other 6 chloro 3 ethoxycarbonyl 4 hydroxycoumarin en
dc.subject.other benzotriazole derivative en
dc.subject.other butyric acid derivative en
dc.subject.other ethyl[(2 acetoxy 3 methoxyphenyl)hydroxymethylidene]ethoxycarbonylacetate en
dc.subject.other ethyl[(2 acetoxy 3 methylphenyl)hydroxymethylidene]ethoxycarbonylacetate en
dc.subject.other ethyl[(2 acetoxy 5 chlorophenyl)hydroxymethylidene]ethoxycarbonylacetate en
dc.subject.other ethyl[(2 acetoxy 5 methylphenyl)hydroxymethylidene]ethoxycarbonylacetate en
dc.subject.other ethyl[(2 acetoxyphenyl)hydroxymethylidene]acetylacetate en
dc.subject.other ethyl[(2 acetoxyphenyl)hydroxymethylidene]benzoylacetate en
dc.subject.other ethyl[(2 acetoxyphenyl)hydroxymethylidene]ethoxycarbonylacetate en
dc.subject.other gamma phenyl beta hydroxybutenoic acid derivative en
dc.subject.other methyl[(2 acetoxyphenyl)hydroxymethylidene]methoxycarbonylacetate en
dc.subject.other n hydroxybenzotriazole en
dc.subject.other unclassified drug en
dc.subject.other unindexed drug en
dc.subject.other acylation en
dc.subject.other article en
dc.subject.other carbon nuclear magnetic resonance en
dc.subject.other chemical reaction en
dc.subject.other cyclization en
dc.subject.other drug structure en
dc.subject.other drug synthesis en
dc.subject.other proton nuclear magnetic resonance en
dc.subject.other reaction analysis en
dc.subject.other stoichiometry en
dc.subject.other structure analysis en
dc.title Novel short-step synthesis of functionalized γ-phenyl-β- hydroxybutenoates and their cyclization to 4-hydroxycoumarins via the N-hydroxybenzotriazole methodology en
heal.type journalArticle en
heal.identifier.primary 10.1055/s-2004-829132 en
heal.identifier.secondary http://dx.doi.org/10.1055/s-2004-829132 en
heal.publicationDate 2004 en
heal.abstract A novel method for the synthesis of functionalized 3-substituted 4-hydroxycoumarins is reported. C-Acylation compounds were derived from the reaction of the N-hydroxybenzotriazole ester of the functionalized acetyl salicylic acids and a variety of active methylene compounds and cyclized to the title compounds. The synthesis is simple and the compounds are produced in yields varying from 39 to 80%. The structure of the newly prepared C-acylation compounds was thoroughly studied through NMR spectroscopy for the first time in the literature. en
heal.journalName Synthesis en
dc.identifier.doi 10.1055/s-2004-829132 en
dc.identifier.issue 11 en
dc.identifier.spage 1775 en
dc.identifier.epage 1782 en


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