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 Citation (Scopus)

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

Fingerprint

Pyridones
Pyridine
Condensation
Fluorescence
Molecules
Isomers
Pyrans
Single crystals
Spectroscopy
X rays
Wavelength
pyridine
2-picoline

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

Cite this

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

In: Synthesis (Germany), Vol. 46, No. 16, ss-2014-m0160-op, 2014, p. 2179-2190.

Research output: Contribution to journalArticle

@article{05afe4eb326149fc99049aca500f0be1,
title = "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",
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.",
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",
author = "Prior, {Allan M.} and Gunaratna, {Medha J.} and Daisuke Kikuchi and John Desper and Yunjeong Kim and Chang, {Kyeong Ok} and Izumi Maezawa and Lee-Way Jin and Hua, {Duy H.}",
year = "2014",
doi = "10.1055/s-0033-1339027",
language = "English (US)",
volume = "46",
pages = "2179--2190",
journal = "Synthesis (Germany)",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "16",

}

TY - JOUR

T1 - 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

AU - Prior, Allan M.

AU - Gunaratna, Medha J.

AU - Kikuchi, Daisuke

AU - Desper, John

AU - Kim, Yunjeong

AU - Chang, Kyeong Ok

AU - Maezawa, Izumi

AU - Jin, Lee-Way

AU - Hua, Duy H.

PY - 2014

Y1 - 2014

N2 - 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.

AB - 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.

KW - 3-substituted 7-methyl-2 H -pyrano[3,2- c ]pyridine-2,5(6 H)-diones

KW - dialkylation

KW - fluorescence probes

KW - heterocycles

KW - tetrahydro-1 H,9 H -2,10-dioxa-9- azaanthracen-1-ones

UR - http://www.scopus.com/inward/record.url?scp=84905719690&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84905719690&partnerID=8YFLogxK

U2 - 10.1055/s-0033-1339027

DO - 10.1055/s-0033-1339027

M3 - Article

AN - SCOPUS:84905719690

VL - 46

SP - 2179

EP - 2190

JO - Synthesis (Germany)

JF - Synthesis (Germany)

SN - 0039-7881

IS - 16

M1 - ss-2014-m0160-op

ER -