title: Syntheses of 3-[(Alkylamino)methylene]-6-methylpyridine-2,4(1H,3H)-diones, 3-Substituted 7-Methyl-2H-pyrano[3,2-c]pyridine-2,5(6H)-dione Fluorescence Probes, and Tetrahydro-1H,9H-2,10-dioxa-9-azaanthracen-1-ones.
abstract: Various condensation and ring-closing reactions were used for the syntheses of 3-[(alkylamino)methylene]-6-methylpyri-dine-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; λabs,max= 350 nm; λem= 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.
authors.affiliation: Department of Chemistry, College of Arts and Sciences, Kansas State University, Manhattan, KS 66506-0401, USA.
authors.forename: Allan M
authors.initials: AM
authors.lastname: Prior
authors.affiliation: Department of Chemistry, College of Arts and Sciences, Kansas State University, Manhattan, KS 66506-0401, USA.
authors.forename: Medha J
authors.initials: MJ
authors.lastname: Gunaratna
authors.affiliation: Department of Chemistry, College of Arts and Sciences, Kansas State University, Manhattan, KS 66506-0401, USA.
authors.forename: Daisuke
authors.initials: D
authors.lastname: Kikuchi
authors.affiliation: Department of Chemistry, College of Arts and Sciences, Kansas State University, Manhattan, KS 66506-0401, USA.
authors.forename: John
authors.initials: J
authors.lastname: Desper
authors.affiliation: Department of Diagnostic Medicine and Pathobiology, College of Veterinary Medicine, Kansas State University, Manhattan, KS 66506-0401, USA.
authors.forename: Yunjeong
authors.initials: Y
authors.lastname: Kim
authors.affiliation: Department of Diagnostic Medicine and Pathobiology, College of Veterinary Medicine, Kansas State University, Manhattan, KS 66506-0401, USA.
authors.forename: Kyeong-Ok
authors.initials: KO
authors.lastname: Chang
authors.affiliation: M.I.N.D. Institute and Department of Pathology, 2825 50th Street, UC Davis Health System, Sacramento, CA 95817, USA.
authors.forename: Izumi
authors.initials: I
authors.lastname: Maezawa
authors.affiliation: M.I.N.D. Institute and Department of Pathology, 2825 50th Street, UC Davis Health System, Sacramento, CA 95817, USA.
authors.forename: Lee-Way
authors.initials: LW
authors.lastname: Jin
authors.affiliation: Department of Chemistry, College of Arts and Sciences, Kansas State University, Manhattan, KS 66506-0401, USA.
authors.forename: Duy H
authors.initials: DH
authors.lastname: Hua
keywords: 3-substituted 7-methyl-2H-pyrano[3,2-c]pyridine-2,5(6H)-diones; dialkylation; fluorescence probes; heterocycles; tetra-hydro-1H,9H-2,10-dioxa-9-azaanthracen-1-ones