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Umlagerungen von Heterocyclen, VII. Ketenoide Umlagerung von 2‐Pyronen zu Naphthalin‐Derivaten
Author(s) -
Kappe Thomas,
Schmidt Heinrich
Publication year - 1979
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19791120745
Subject(s) - chemistry , medicinal chemistry , yield (engineering) , metallurgy , materials science
Rearrangement Reactions of Heterocycles, VII. Ketenoid Rearrangement of 2‐Pyrones to Naphthalenes 4‐Hydroxy‐2‐pyrones 3, obtained by the condensation reaction of trichlorophenyl malonates 1 with the ketones 2 at 240°C, are rearranged at 260°C via ketenes 6 to yield 1,3‐dihydroxynaphthalenes 5. The latter are readily oxidized to naphthoquinones 4 by air. A side product in the rearrangement of 3b is triphenylphloroglucinol ( 7 ).
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