Hydrazones and oximes are common conjugates, but are labile to hydrolysis. The hydrolytic stability of isostructural hydrazones and an oxime have been determined at pD 5.0–9.0. The hydrolysis of each adduct was catalyzed by acid. Rate constants for oxime hydrolysis were nearly 103-fold lower than those for simple hydrazones; a trialkylhydrazonium ion (formed after condensation) was even more stable than the oxime. The data suggest a general mechanism for conjugate hydrolysis.
Synthesis of Perhydro-1,3,4-thiadiazin-5-ones and 3-Arylaminothiazolidin-4-ones by the Regioselective Cyclocondensation of 2-Sulfanylalkanoic Acids or Their Silyl Esters with Methyl and Aryl Hydrazones
作者:Yoo Tanabe、Masaki Nagaosa、Yoshinori Nishii
DOI:10.3987/com-95-7151
日期:——
Perhydro-1,3,4-thiadiazin-5-ones and 3-arylaminothiazolidin-4-ones were prepared by the highly regioselective cyclocondensation of 2-sulfanylalkanoic acids with methyl- and arylhydrazones, respectively. A similar reaction using trimethylsilyl 2-sulfanylalkanoates in the place of the acids proceeded under milder conditions with tetrabutylammonium fluoride catalyst.