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
dc.citation.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.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.contributor.authoreid | desperj | en_US |
dc.contributor.authoreid | ykim | en_US |
dc.contributor.authoreid | kchang | en_US |
dc.contributor.authoreid | duy | en_US |
dc.date.accessioned | 2014-11-14T17:04:17Z | |
dc.date.available | 2014-11-14T17:04:17Z | |
dc.date.issued | 2014-11-14 | |
dc.date.published | 2014 | en_US |
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.identifier.uri | http://hdl.handle.net/2097/18672 | |
dc.language.iso | en_US | en_US |
dc.relation.uri | https://doi.org/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 |