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Potassium fluoride‐promoted reaction of (2‐chloro‐2‐nitroethenyl)benzenes with 1,3‐dicarbonyl compounds. A general synthesis of 6,6‐dimethyl‐2‐nitro‐3‐phenyl‐3,5,6,7‐tetrahydro‐4(2 H )benzofuranones and some analogs
Author(s) -
Dauzonne Daniel,
Demerseman Pierre
Publication year - 1990
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.5570270611
Subject(s) - chemistry , dibenzoylmethane , ethyl acetoacetate , potassium fluoride , nitro , fluoride , potassium , medicinal chemistry , organic chemistry , catalysis , inorganic chemistry , alkyl
A convenient procedure to prepare in good yields 6,6‐dimethyl‐2‐nitro‐3‐phenyl‐3,5,6,7‐tetrahydro‐4(2 H )‐benzofuranones starting from (2‐chloro‐2‐nitroethenyl)benzenes and 5,5‐dimethyl‐1,3‐cyclohexanedione in the presence of potassium fluoride is reported. This method also proved efficient with other 1,3‐dicarbonyl compounds, and has been successfully extended to 1,3‐cyclohexanedione, 2,5‐pentanedione, dibenzoylmethane and ethyl acetoacetate.