Synthesis of Aniline Derivatives with Potential Toxicological Implications to the Spanish Toxic Oil Syndrome

Abstract

AbstractThe synthesis of anilides 2 from several saturated and unsaturated fatty acids 1 required for toxicological studies related to the Spanish Toxic Oil Syndrome is reported. In addition, a simple procedure for the microscale determination of the position of a carbon–carbon double bond of a fatty acid residue is described. This procedure involves epoxidation of the sample with 3,3‐dimethyldioxirane followed by oxidative cleavage with periodic acid to yield the corresponding carbonyl derivatives which are easily identifiable by GC‐MS analysis. Finally, the synthesis of anilino derivatives 5–8 formally derived from glycerol is also reported. For this purpose, a common precursor, i.e. 3‐(phenylamino)propane‐1,2‐diol (4) is prepared, and convenient procedures for its chemoselective acylation at either the hydroxy or the amino group have been developed.