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Chromium trioxide oxidation products from 4‐spiro‐1‐phenylisochromans
Author(s) -
Gatta Franco,
Settimj Guido
Publication year - 1983
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570200524
Subject(s) - chemistry , cyclopentane , chromium trioxide , hydrazine (antidepressant) , piperidine , acetic acid , chromium , medicinal chemistry , organic chemistry , chromatography
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‐4 H ‐2,3‐benzodiazepin‐4‐ones IIIa or XIa.