6533b824fe1ef96bd12815b2
RESEARCH PRODUCT
Unexpected Behavior of Enaminones: Interesting New Routes to 1,6-Naphthyridines, 2-Oxopyrrolidines and Pyrano[4,3,2-de][1,6]naphthyridines
Herbert MeierMoustafa Sherief MoustafaMohamed Hilmy ElnagdiJohannes C. LiermannNoha M. HilmyYehia A. IbrahimSaleh Mohammed Al-mousawisubject
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 Chemistrydescription
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 ethyl ester 15B.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2012-12-27 | Molecules |