Search results for "enaminones"

showing 2 items of 2 documents

Unexpected Behavior of Enaminones: Interesting New Routes to 1,6-Naphthyridines, 2-Oxopyrrolidines and Pyrano[4,3,2-de][1,6]naphthyridines

2012

Reaction of enaminones 1a–d with 2-aminoprop-1-ene-1,1,3-tricarbonitrile (2) in the presence of AcOH/NH4OAc afforded 7-amino-5-oxo-5,6-dihydro-1,6-naphthyridine-8-carbonitrile derivatives 9a–d. On the other hand, 2-aminopyrano[4,3,2-de] [1,6]naphthyridine-3-carbonitriles 20a–c,e were the only obtained products from the reactions of 1a–d with 2 in the presence of AcOH/NaOAc, while 1d afforded [3,5-bis-(4-chloro-benzoyl)-phenyl]-(4-chloro-phenyl)-methanone 21 under the same condition. The reaction of 2 with diethyl acetylenedicarboxylate in the presence of AcOH/NH4OAc afforded (4-cyano-5-dicyanomethylene-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)-acetic acid eth…

7-amino-5-oxo-56-dihydro-16-naphthyridine-8-carbonitrileMagnetic Resonance Spectroscopy2-aminoprop-1-ene-113-tricarbonitrileMolecular StructureChemistryOrganic ChemistryPharmaceutical ScienceEthyl esterMedicinal chemistryArticleAnalytical Chemistrylcsh:QD241-441Diethyl acetylenedicarboxylate3-amino-2-cyanopent-2-enedinitrilelcsh:Organic chemistryChemistry (miscellaneous)enaminonesNitrilesDrug DiscoveryTransition TemperatureMolecular Medicineenaminones; 3-amino-2-cyanopent-2-enedinitrile; 7-amino-5-oxo-56-dihydro-16-naphthyridine-8-carbonitrile; 2-aminoprop-1-ene-113-tricarbonitrileNaphthyridinesPhysical and Theoretical ChemistryMolecules
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A novel synthetic approach to pyran-2,4-dione scaffold production : microwave-assisted dimerization, cyclization, and expeditious regioselective conv…

2020

Here, we report a novel, green, simple, low-cost, and rapid methodology for the high-yield production of pyran-2,4-dione scaffolds under microwave irradiation. Regio- and stereoselective conversions of β-diketone systems into β-enaminones were achieved using 18 primary amines and four amino acid esters. Microwave-assisted further cyclization of 3-(β-substitutedvinyl)-6-phenyl-pyran-2,4-dione into 3-benzoyl-4,7-diphenyl-2H,5H-pyrano[4,3-b]pyran-2,5-dione via reaction with ethyl benzoyl acetate. peerReviewed

kemiallinen synteesimikroaallotmicrowavepyran-24-dioneintramolecular cyclizationorgaaniset yhdisteetβ-enaminones
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