Preparation and Steric Structure of Condensed-Skeleton Saturated Diphenyl-substituted Isoindolones
1994; Elsevier BV; Volume: 38; Issue: 5 Linguagem: Inglês
10.3987/com-93-6660
ISSN1881-0942
AutoresGéza Stájer, Angela E. Szabó, G. BERNÁTH, Pàl Sohár,
Tópico(s)Coordination Chemistry and Organometallics
ResumoThe Friedel-Crafts reaction of benzene with cis-4-cyclohexene-1,2-dicarboxylic anhydride (1) yields tram-5-phenyl-ck-2-benzoylcyclohexanecarboxylic acid (2), which gave cyclohexane-condensed pyridazinone (3) with hydrazine, and ck-4,5-tetramethylene-1,2-oxazin-8-one (4) with hydroxylamine.From 2 with ethylenediamine, the saturated imidazo[2,3-alisoindolone ( 5 ) was prepared, while the reaction of 2 with 1,3-diaminopropane furnished a mixture of two isomeric pyrimido[2,3-a]isoindnlones (6a,b) differing in the relative positions of the benzene ring and cyclohexane amelation hydrogens.From the reaction of 2 with 3-aminopropanol, the oxazino[2,3-u]isoindnlone (7) was obtained.The reaction of 2 with cis-2-hydroxymethylcyclohexylamine gave the tetracyclic (S), while 2 and diendo-3-hydroxymethylhicyc1o[2.2.l]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.'H-and 13C-nmr spectra and DNOE and 2D-HSC measurements proved that the 5-phenyl group is ck-equatorial to the two amelated hydrogens of the cyclohexane ring.
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