| Abstract: | Chromium trioxide oxidation of 1-phenylisochroman-4-spiro-1′-cyclopentane (Ia) in acetic acid led to the expected 1-(2-benzoylphenyl)cyclopentanecarboxylic acid (IIa), while its 6,7-dimethoxy analogue Ib and 6,7-dimethoxy-1-phenylisochroman-4-spiro-4′-(1′-methyl)piperidine (Ic) under the same conditions gave a mixture of their related 1-hydroxy derivatives VIIIb and VIIIc and of the p-benzoquinones, 1-benzoyloxymethyl-1-(2,5-dioxo-4-methoxyphenyl)cyclopentane (IXb) and 1-benzoyloxymethyl-1-(2,5-dioxo-4-methoxyphenyl)-1-methylpiperidine (IXc). Cyclization of Ila with hydrazine or monomethylhydrazine led to the 5-spiro-substituted 1-phenyl-3,5-dihydro-4H-2,3-benzodiazepin-4-ones IIIa or XIa. |
