title: Unexpected behavior of enaminones: interesting new routes to 1,6-naphthyridines, 2-oxopyrrolidines and pyrano[4,3,2-de][1,6]naphthyridines.
abstract: 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.
authors.affiliation: Department of Chemistry, Faculty of Science, University of Kuwait, P.O. Box 5969, Safat 13060, Kuwait. mostafa_msm@hotmail.com
authors.forename: Moustafa Sherief
authors.initials: MS
authors.lastname: Moustafa
authors.forename: Saleh Mohammed
authors.initials: SM
authors.lastname: Al-Mousawi
authors.forename: Noha Mohamed
authors.initials: NM
authors.lastname: Hilmy
authors.forename: Yehia A
authors.initials: YA
authors.lastname: Ibrahim
authors.forename: Johannes C
authors.initials: JC
authors.lastname: Liermann
authors.forename: Herbert
authors.initials: H
authors.lastname: Meier
authors.forename: Mohamed Hilmy
authors.initials: MH
authors.lastname: Elnagdi
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis / Q000737:chemistry*; D009570:Nitriles / Q000138:chemical synthesis*; D044366:Transition Temperature
chemical_list: C581496:7-amino-5-oxo-5,6-dihydro-1,6-naphthyridine-8-carbonitrile; D009287:Naphthyridines; D009570:Nitriles