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Cinnolines. X. The oxidative‐rearrangement of 1‐aminooxindoles to 3‐cinnolinols
Author(s) -
Baumgarten Henry E.,
Wittman William F.,
Lehmann Gerhard J.
Publication year - 1969
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.5570060311
Subject(s) - chemistry , nitrene , oxidative phosphorylation , hypochlorite , computational chemistry , medicinal chemistry , organic chemistry , photochemistry , biochemistry , catalysis
An improved route for the oxidative‐rearrangement of 1 ‐aminooxindoles, treatment with equimolar amounts of t ‐butyl hypochlorite, produces nearly quantitative yields of 3‐cinnolinols of excellent purity. The syntheses of the previously inaccessible 4‐ and 6‐ehloro‐1‐armnooxin‐doles has shown that this method, first applied to 1‐aminooxindole, may be reasonably general. The mechanism of this reaction is discussed in terms of nitrene and nitrenoid intermediates.