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 language | English (US) |
|---|---|
| Article number | ss-2014-m0160-op |
| Pages (from-to) | 2179-2190 |
| Number of pages | 12 |
| Journal | Synthesis (Germany) |
| Volume | 46 |
| Issue number | 16 |
| DOIs | |
| State | Published - 2014 |
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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 journal › Article
}
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 -