Synthesis and N-substitution of an uncommon heterocyclic system: Oxazolo[5,4-b]pyridin-2(1H)-one

Flouzat, C.; Blanchet, M.; Guillaumet, Gérald

doi:10.1016/s0040-4039(00)61315-1

Cited by 17 publications

(3 citation statements)

References 9 publications

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“…For this purpose, Deprotonation of pyrazolo [3,4-b]pyridine-3-one 3 with sodium hydride and further nucleophilic substitution with dibromoethane allows the alkylation of position 1 and compound 7 was isolated in 60% yield (Scheme 2) [12]. We then carried out the preparation of the decahydropyrido[1,2-a][1,4]diazepine 6.…”

Section: Resultsmentioning

confidence: 99%

“…The solution was hydrolyzed and extracted with CH 2 Cl 2 . The organic extracts were dried over MgSO 4 2-(1-(4-Methoxybenzyl)-4-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazolo [3,4-b]pyridin-6-yl)ethyl methanesulfonate (12). 0.63 mL (7.71 mmol; 5 eq) of pyridine were added to 600 mg (1.54 mmol; 1 eq) of alcohol 10 in 15 mL of CH 2 Cl 2 at 0 C. The solution was stirred 45 min at 0 C then 0.30 mL (3.86 mmol; 2.5 eq) of mesyl chloride in 2 mL of CH 2 Cl 2 are run.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of new compounds containing the pyrazolo[3,4‐b]pyridine‐3‐one subunit

Fadel

Suzenet

Hafid

et al. 2009

Journal of Heterocyclic Chem

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in Wiley InterScience (www.interscience.wiley.com).A convenient route for the synthesis of pyrazolo [3,4-b]pyridine-3-ones via condensation of 3-amino-1-phenylpyrazolin-5-one with 4-hydroxy-6-methylpyran-2-one is described. The pyrazolo[3,4-b]pyridine-3-one isomers obtained were functionalized at 1-, 4-, or 6-position by different pharmacophore entities allowing the synthesis of new compounds with promising biological activities.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis of new compounds containing the pyrazolo[3,4‐b]pyridine‐3‐one subunit

Fadel

Suzenet

Hafid

et al. 2009

Journal of Heterocyclic Chem

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“…1 -(4-Bromobutyl)oxazolo [5,[4][5][6] pyridin-2( Iff)-one (13). Compound 13 was prepared similarly to 11, with 1,4-dibromobutane as starting reagent, and obtained with a yield of 64%: mp 50 °C; IR (KBr) 3100-2900, 1760, 1620 cm"1; 3H NMR (CDC13) ( l-(5-Bromopentyl)oxazolo [5,4-f>]pyridin-2(LH)-one (14).…”

Section: Methodsmentioning

confidence: 99%

N-Substituted Oxazolo[5,4-b]pyridin-2(1H)-ones: A New Class of Non-Opiate Antinociceptive Agents

Viaud

Jamoneau²,

Flouzat³

et al. 1995

J. Med. Chem.

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A series of 1-(aminoalkyl)- and 1-[(4-aryl-1-piperazinyl)alkyl]oxazolo[5,4-b]pyridin-2(1H)-one derivatives of oxazolo[5,4-b]pyridin-2(1H)-one, incorporating modifications to the length of the alkyl side chain and to the amino or 4-aryl-1-piperazinyl substituents, were tested for safety and analgesic efficacy in mice and rats. Some compounds with 4-(substituted or nonsubstituted phenyl)-1-piperazinyl substituents and a 3-4-carbon alkyl side chain had significantly greater analgesic activity than that of the oxazolo[4,5-b]pyridin-2(3H)-one analogs. To reduce the metabolic N-dealkylation of the piperazine observed in our previous work on oxazolo[4,5-b]-pyridin-2(3H)-ones, analogs of the most active compounds with steric hindrance on the alkyl side chain were prepared and tested. The compound with the maximal combination of safety and analgesic efficacy was 1-[[4-(4-fluorophenyl)-1-piperazinyl]propyl]oxazolo[5,4-b]pyridin- 2(1H)-one (compound 3b), with ED50 values of 5.6 mg/kg po (mouse, phenylquinone writhing test) and 0.5 mg/kg po (rat, acetic acid writhing test). Compound 3b is a potent, rapid-acting, non-opioid, nonantiinflammatory analgesic with low acute toxicity and sustained effect.

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Bis(trichloromethyl) Carbonate

Roestamadji

Mobashery

2001

Encyclopedia of Reagents for Organic Synthesis

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Synthesis and N-substitution of an uncommon heterocyclic system: Oxazolo[5,4-b]pyridin-2(1H)-one

Cited by 17 publications

References 9 publications

Synthesis of new compounds containing the pyrazolo[3,4‐b]pyridine‐3‐one subunit

Synthesis of new compounds containing the pyrazolo[3,4‐b]pyridine‐3‐one subunit

N-Substituted Oxazolo[5,4-b]pyridin-2(1H)-ones: A New Class of Non-Opiate Antinociceptive Agents

Bis(trichloromethyl) Carbonate

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