Syntheses of 3-[(Alkylamino)methylene]-6-methyl-1Hpyridine-2,4-diones, Fluorescence Probes 3-Substituted 7-Methyl-6H-pyrano[3,2-c]pyridine-2,5-diones, and Tetrahydro-6H-2,10-dioxa-9-azaanthracen-1-ones

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dc.contributor.author Prior, Allan M.
dc.contributor.author Gunaratna, Medha J.
dc.contributor.author Kikuchi, Daisuke
dc.contributor.author Desper, John
dc.contributor.author Kim, Yunjeong
dc.contributor.author Chang, Kyeong-ok
dc.contributor.author Maezawa, Izumi
dc.contributor.author Jin, Lee-Way
dc.contributor.author Hua, Duy H.
dc.date.accessioned 2014-11-14T17:04:17Z
dc.date.available 2014-11-14T17:04:17Z
dc.date.issued 2014-11-14
dc.identifier.uri http://hdl.handle.net/2097/18672
dc.description.abstract Various condensation and ring-closing reactions were used for the syntheses of 3-[(alkylamino)methylene]-6-methylpyridine-2,4(1H,3H)-diones, bicyclic pyridinones, and tricyclic morpholinopyrones. For instance, 3-[(dialkylamino)methylene]-6-methylpyridine-2,4(1H,3H)-diones were synthesized from the condensation of dialkylamines and 3-formyl-4-hydroxy-6-methylpyridin-2(1H)-one. 3-Formyl-4-hydroxy-6-methylpyridin-2(1H)-one, derived from 3-formyl-4-hydroxy-6-methylpyridin-2(1H)-one, was used to construct a number of bicyclic pyridinones via a one-pot Knoevenagal and intramolecular lactonization reaction. Tricyclic morpholinopyrones were assembled from a dialkylation reaction involving a dinucleophile, 3-amino-4-hydroxy-6-methyl-2H-pyran-2-one, and a dielectrophile, trans-3,6-dibromocyclohexene. Depending on the reaction conditions, isomers of the tricyclic molecules can be selectively produced, and their chemical structures were unequivocally determined using single-crystal X-ray analyses and 2D COSY spectroscopy. The fluorescently active bicyclic pyridinone compounds show longer absorption (368–430 nm; maximum) and emission wavelengths (450–467 nm) than those of 7-amino-4-methylcoumarin (AMC; λ[subscript abs,max] = 350 nm; λ[subscript em] = 430 nm) suggesting these molecules, such as 3-(2-aminoacetyl)-7-methyl-2H-pyrano[3,2-c]pyridine-2,5(6H)-dione, can be employed as fluorescence activity based probes for tracing biological pathways. en_US
dc.language.iso en_US en_US
dc.relation.uri https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0033-1339027 en_US
dc.rights Supplemental information for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084 en_US
dc.subject Dialkylation en_US
dc.subject Fluorescence probes en_US
dc.subject Heterocycles en_US
dc.subject 3- substituted 7-methyl-6H-pyrano[3,2-c]pyridine-2,5-diones en_US
dc.subject tetrahydro-6H-2,10-dioxa-9-azaanthracen-1-ones en_US
dc.title Syntheses of 3-[(Alkylamino)methylene]-6-methyl-1Hpyridine-2,4-diones, Fluorescence Probes 3-Substituted 7-Methyl-6H-pyrano[3,2-c]pyridine-2,5-diones, and Tetrahydro-6H-2,10-dioxa-9-azaanthracen-1-ones en_US
dc.type Article (author version) en_US
dc.date.published 2014 en_US
dc.citation.doi doi:10.1055/s-0033-1339027 en_US
dc.citation.epage 2190 en_US
dc.citation.issue 16 en_US
dc.citation.jtitle Synthesis en_US
dc.citation.spage 2179 en_US
dc.citation.volume 46 en_US
dc.contributor.authoreid desperj en_US
dc.contributor.authoreid ykim en_US
dc.contributor.authoreid kchang en_US
dc.contributor.authoreid duy en_US


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