W. Reeve, W. Coley
Feb 15, 1979
Citations
0
Influential Citations
12
Citations
Journal
Canadian Journal of Chemistry
Abstract
Phenyl(trichloromethyl)carbinol reacts with bifunctional reagents containing nucleophilic sulfur such as thioureas, thiobenzhydrazide, o-aminothiophenol, etc., in a series of steps involving an initial attack of the sulfur anion on the intermediate epoxide 2 followed by ring closure to a heterocyclic compound. Thiazolidinones, thiadiazinones, benzothiazinones, and thiomorpholinones are easily obtained in yields ranging from 57–20%. Monosubstituted ureas react to give exclusively the 2-substituted iminothiazolidinones. Evidence is presented that these are actually in the aminothiazolone form with considerable zwitterionic character. 1,3-Disubstituted ureas do not give heterocyclic products. The reaction works particularly well with those nucleophiles which are stable to base, contain a sulfur nucleophilic center for the initial step of the reaction (2 to 3) and an amino or imino group properly positioned for the final ring closure to the heterocyclic compound.Hydroxylamine forms α-oximinophenylacetohydroxa...