Syntheses of 3-[(Alkylamino)methylene]-6-methylpyridine-2,4(1 H,3 H)-diones, 3-substituted 7-methyl-2 H -pyrano[3,2- c ]pyridine-2,5(6 H)-dione fluorescence probes, and tetrahydro-1 H,9 H -2,10-dioxa-9-azaanthracen-1-ones

Allan M. Prior, Medha J. Gunaratna, Daisuke Kikuchi, John Desper, Yunjeong Kim, Kyeong Ok Chang, Izumi Maezawa, Lee-Way Jin, Duy H. Hua

Research output: Contribution to journalArticle

1 Scopus citations

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; 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.

Original languageEnglish (US)
Article numberss-2014-m0160-op
Pages (from-to)2179-2190
Number of pages12
JournalSynthesis (Germany)
Volume46
Issue number16
DOIs
StatePublished - 2014

Keywords

  • 3-substituted 7-methyl-2 H -pyrano[3,2- c ]pyridine-2,5(6 H)-diones
  • dialkylation
  • fluorescence probes
  • heterocycles
  • tetrahydro-1 H,9 H -2,10-dioxa-9- azaanthracen-1-ones

ASJC Scopus subject areas

  • Organic Chemistry
  • Catalysis

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