title: Utilization ofN-acyl compounds for the synthesis of tricyclic and bridged heterocyclic compounds.
abstract: N-acyl derivative4was prepared via the reaction of methyl anthranilate with ethyl bromoacetate then refluxing the formed amino ester3with acetic anhydride. Cyclization of4in presences of sodium methoxide and methanol forming 2,4-pyrrolidindione derivative5. 2,4-Quinolidinone6was obtained via cyclization of4in dry toluene and sodium hydride. On the other hand, indolinone derivative8was obtained by cyclization of4in toluene and free from alcohol due to retro Diekmann-condensation. On treatment of8with sodium hydride, refluxing toluene and in presences of Crown ether gave tricyclic compound9. Also, treatment of 2-pyrrolidinone with trimethylene chlorobromide produced10which cyclized using base and solvent to the bridged ring derivatives11. The acidic hydrolysis of11afforded the corresponding amino acid13. Whereas derivative14was obtained by the reaction of 2-pyrrolidinone with ethyl 3-bromopropionate which on cyclization gave azabicyclo[3,2,1]octan-4,8-dione derivative15. Compound15underwent acidic hydrolysis to the amino ketone derivative azepanone hydrochloride17.
authors.forename: Mohamed A
authors.initials: MA
authors.lastname: Waly
authors.forename: Fawzia Z
authors.initials: FZ
authors.lastname: El-Ablack
keywords: 2,4-pyrrolidindione; Carboxy azepane; Indolinone; azepanone hydrochloride; quinolidinone; tricyclic compound