A deacetylation-diazotation-coupling sequence: Palladium-catalyzed C-C bond formation with acetanilides as formal leaving groups
Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki crosscoupling reactions, and a Pd-catalyzed [2+2+1] cycloaddition hav
Schmidt, Bernd,Berger, Rene
supporting information
p. 463 - 476
(2013/05/08)
Topical anti-inflammatory activity of boropinic acid and its natural and semi-synthetic derivatives
Boropinic acid is a natural isopentenyloxycinnamic acid extracted from the aerial parts of Boronia pinnata Sm. (Rutaceae) with soybean 5-lipoxygenase inhibitory activity. In this paper the topical anti-inflammatory activity of boropinic acid and some of its natural and semi-synthetic derivatives was evaluated using the Croton oil ear test in mice as a model of acute inflammation. Some of the tested compounds (15, 17, 19, 20) revealed an effect comparable (ID50 = 0.18 ÷ 0.72 μmol/cm2) to that of the reference drug indomethacin (ID50 = 0.23 μmol/cm 2), a non-steroidal anti-inflammatory drug.
Epifano, Francesco,Sosa, Silvio,Tubaro, Aurelia,Marcotullio, M. Carla,Curini, Massimo,Genovese, Salvatore
supporting information; experimental part
p. 769 - 772
(2011/03/18)
Mizoroki-heck reactions with 4-phenoldiazonium salts
Significantly better yields were achieved in Mizoroki-Heck reactions using 4-phenoldiazonium salts instead of their O-alkylated analogues under otherwise identical conditions. We found that a one-flask deacetylation-diazotation- precipitation sequence starting from paracetamol or acetanilides derived thereof provides a convenient access to the required diazonium tetrafluoroborates. The utility of these arylating agents in palladium-catalyzed C-C bond forming reactions was demonstrated for a one-flask-synthesis of the heterocyclic core of the drug aripiprazole. Notably, the diazonium salt formation from an acetanilide could be combined with two Pd-catalyzed steps in a one-flask sequence, without any exchange of solvents or isolation of intermediates.