The Behaviour of Some Acylthiosemicarbazides in the Reaction with a-Halogenated Esters

Abstract

New six unexpected 1,3,4-oxadiazoles were obtained starting from acylthiosemicarbazides. N1-[4-(4-X-phenylsulfonyl)benzoyl]-N4-(2/3-methoxyphenyl)-thiosemicarbazides 2,3a-c were treated with ethyl chloro- or bromoacetate in presence of anhydrous sodium acetate in order to obtain new thiazolidin-4-ones compounds. However, formation of desired thiazolidin-4-ones from these acylthiosemicarbazides failed and instead 1,3,4-oxadiazoles were obtained. For confirmation presence of these compounds, 5-[4-(phenylsulfonyl)phenyl]-2-(3-methoxyphenylamino)-1,3,4-oxadiazole 5a was synthetized by cyclodesulfurization of acylthiosemicarbazide 3a with mercury (II) acetate. The structures of these compounds were elucidated by FTIR, UV, 1H-NMR and 13C-NMR, MS spectra and elemental analysis.

Synthesis and Biological Evaluation of Some NewN1-[4-(4-Chlorophenylsulfonyl)benzoyl]-N 4-(aryl)-thiosemicarbazides and Products of Their Cyclization

“…The signals corresponding to protons and carbons from 4‐(4‐chlorophenylsulfonyl)phenyl, 2‐fluorophenyl, 4‐trifluoromethoxyphenyl, and 3,4,5‐trimethoxyphenyl moieties appeared in 1 H and 13 CNMR spectra of new compounds 2–10 at the expected chemical shifts .…”

S-Alkylated 1,2,4-Triazoles Derivatives Synthesis, spectral analysis and cytotoxicity evaluation

“…The alkylated derivatives presented in this paper, whose reaction scheme was presented in previous work [22], were prepared starting from 1,2,4-triazole-3-thiones 2a,b known in literature [23,24] that have been synthesized by cyclization of the corresponding acylthiosemicarbazides 1a,b in a 8% sodium hydroxide solution.…”

Coordination Compounds of Some 3d-Transition Metal Ions with N1-[4-(4-bromo-phenylsulfonyl)-benzoyl]-N4-(4-methoxyphenyl)- thiosemicarbazide

“…Thermal analysis has been carried out with a TGA V5.1A DuPont 2000 derivatograph. L 1 was synthesized by following the method described in reference [5].…”