ChemInform Abstract: 2‐PHENYL‐1,3,4‐THIADIAZOL‐2‐INES

Abstract

Das Thiobenzhydrazid (I) reagiert mit Aldehyden und Ketonen zu Thiadiazolinen (III) bzw. (V).

Development of Chlamydial Type III Secretion System Inhibitors for Suppression of Acute and Chronic Forms of Chlamydial Infection

“…It was ascertained via the analysis of the published data [18, 19] that ring–chain tautomerism is typical of thiohydrazones. Cyclic tautomers (thiadiazolines II ) are easily oxidized by air oxygen, yielding inactive and toxic thiadiazoles III ( Fig.…”

Development of Chlamydial Type III Secretion System Inhibitors for Suppression of Acute and Chronic Forms of Chlamydial Infection

“…It was ascertained via the analysis of the published data [ 18 , 19 ] that ring–chain tautomerism is typical of thiohydrazones. Cyclic tautomers (thiadiazolines II ) are easily oxidized by air oxygen, yielding inactive and toxic thiadiazoles III ( Fig.…”

Recyclizations of 2‐aminobenzylimines and thioaroylhydrazones of N‐substituted N‐hydroxy‐3‐oxobutanamides

“…Calcd. for C 19 This compound was obtained in 90% yield, mp 151-152 ºC. Spectral data for this compound are presented in Table 1.…”

“…The unmistakably cyclic (both in polar and non-polar solvents) structures III (Table 1) are identified as IIIC by the carbon signals at δ C 78.2-81.4 ppm corresponding to the C-5 atoms of 1,3,4-thiadiazolines [19]. The C-5 signals of structures IIIB should be shifted beyond 90 ppm [18].…”

“…The same is true for the products obtained by substitution of their hemiacetal hydroxyl group with certain hydrazine derivatives [18]. On the other hand, the condensation between carbonyl compounds and either 2-aminomethylaniline or thioaroylhydrazines leads to cyclic structures 1,3,4-∆ 2 -thiadiazolines [19] or (1,2,3,4-tetrahydroquinazolines [20], respectively). These heterocycles can exhibit ring-chain tautomerism, which was indeed observed in 1,3,4-∆ 2 -thiadiazolines [21,22].…”