ABSTRACT
A regioselective green synthesis of nitroacetaminophen derivatives was carried out by electrochemical oxidation of acetaminophen, N-(2-hydroxyphenyl)acetamide, and 1-(4-(4-hydroxyphenyl)piperazin-1-yl)ethanone in the presence of nitrite ion as a nucleophile. The present work has led to the development of a reagentless green and facile electrochemical method for the synthesis of some nitroacetaminophen derivatives.
Subject(s)
Acetaminophen/analogs & derivatives , Nitrates/chemical synthesis , Acetaminophen/chemical synthesis , Acetaminophen/chemistry , Acetaminophen/pharmacology , Acetanilides/chemistry , Molecular Structure , Nitrates/chemistry , Nitrates/pharmacology , Piperazines/chemistry , StereoisomerismABSTRACT
The 1:1 imine intermediate generated by the addition of benzyl amine to cyclobutanone is trapped by (N-isocyanimino)triphenylphosphorane in the presence of an aromatic carboxylic acid leads to the formation of the corresponding iminophosphorane intermediate. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature. The disubstituted 1,3,4-oxadiazole derivatives, were produced in excellent yields.
