Synthesis of the N-oxides of phenothiazine antipsychotic agents.
Chlorpromazine N-oxide, fluphenazine N4'-oxide, prochlorperazine N4'-oxide, sulforidazine N-oxide, and trifluoperazine N4'-oxide were synthesized by oxidation of the designated nitrogen atom in the N-10 side chain of the respective parent drug with 3-chloroperoxybenzoic acid. In the case of trifluoperazine, a stepwise increase in the amount of oxidant yielded the N1',N4'-dioxide and N1',N4',S-trioxide. The N',S-dioxides of chlorpromazine and sulforidazine were obtained by hydrogen peroxide oxidation of the appropriate parent drug.
Jaworski
T J
TJ
College of Pharmacy, University of Saskatchewan, Saskatoon, Canada.
Sardessai
M S
MS
Aravagiri
M
M
Lin
G
G
Shi
Y Y
YY
Hawes
E M
EM
Hubbard
J W
JW
McKay
G
G
Midha
K K
KK
D014150:Antipsychotic Agents / Q000138:chemical synthesis*; D003497:Cyclic N-Oxides / Q000138:chemical synthesis*; D010640:Phenothiazines
D014150:Antipsychotic Agents; D003497:Cyclic N-Oxides; D010640:Phenothiazines