[Preparation and steric structure of condensed-skeleton saturated diphenyl-substituted isoindolones].
The Friedel-Crafts reaction of benzene with cis-4-cyclohexene-1,2-dicarboxylic anhydride (1) yields trans-5-phenyl-cis-2-benzoylcyclohexanecarboxylic acid (2), which gave cyclohexane-condensed pyridazinone (3) with hydrazine, and cis-4,5-tetramethylene-1,2-oxazin-8-one (4) with hydroxylamine. From 2 with ethylenediamine, the saturated imidazol[2,3-a]iso-indolone (5) was prepared, while the reaction of 2 with 1,3-diaminopropane furnished a mixture of two isomeric pyrimido[2,3-a]isoindolones (6a,b) in the relative positions of the benzene ring and cyclohexane annelation hydrogens. From the reaction of 2 with 3-aminopropanol, the oxazino[2,3-a]isoindolone (7) was obtained. The reaction of 2 with cis-2-hydroxymethylcyclohexylamine gave the tetracyclic (8), while 2 and diendo-3-hydroxymethylbicyclo[2.2.1]hept-5-enyl-2-amine yielded the isomers (9a,b), which differ in the mutual positions of the phenyl group on the quaternary carbon and cyclohexane annelation hydrogens. 1H and 13C-nmr spectra and DNOE and 2D-HSC measurements proved that the 5-phenyl group is cis-equatorial to the two annelated hydrogens of the cyclohexane ring.
Stájer
G
G
Szent-Györgyi Albert Orvostudományi Egyetem Gyógyszerészi Vegytani Intézet, Szeged.
Szabó
E A
EA
Bernáth
G
G
Sohár
P
P
D006834:Hydrazines; D007202:Indicators and Reagents; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D010078:Oxazines
D006834:Hydrazines; D007202:Indicators and Reagents; D007211:Indoles; D010078:Oxazines; C029424:hydrazine
Kondenzáltvázas telített difenilszubsztituált izoindolonok elöállítása és szerkezete.