Reaction of Hydrazonyl Halides with Derivatives of Thiourea and Thiosemicarbazide; A New Source of C-Amino- and C-Hydrazino-1,2,4-triazoles

Abstract

Reaction of hydrazonyl halides with (substituted) thioureas and thiosemicarbazides gives mainly 1,3,4-thiadiazolines, the stronger base being preferentially eliminated in the process. Similar reactions in presence of triethylamine give C-amino- and C-hydrazino-1,2,4-triazoles, respectively, together with the hydrazonyl sulfide.Potassium cyanide cleavage of a hydrazonyl disulfide gives the corresponding 1,3,4-thiadiazoline and thiohydrazide.

Reactions with Hydrazonoyl Halides. Part 20.1 Synthesis of New Unsymmetrical Azines, Dihydro-1,3,4-thiadiazoles and 5-Arylazothiazoles

“…3,4 Treatment of hydrazonoyl chlorides 1a±c with methyl phenyldithiocarbamate (2) gave one isolable product in each case. The reaction of 1a with phenylthiourea in boiling ethanol gave an identical product, 12 in all respects (mp, mixed mp and spectra), to that obtained before. Consequently, the product was identi®ed as 3,5-diphenyl-2-N-phenylimino-2,3-dihydro-1,3,4-thiadiazole (5a).…”

Synthesis and Reaction of Novel Spiro Pyrimidine Derivatives

“…Moreover, stirring under reflux 2‐mercapto‐6‐[(pyridin‐4‐ylmethylene)‐amino]‐3 H ‐pyrimidin‐4‐one 1 with hydrazonoyl chloride derivatives 2a , 2b , 2c , 2d in dry chloroform for 4 h under TLC control afforded 2‐( S ‐p‐( S )‐phenylazo‐methylsulfanyl)‐6‐[(pyridine‐4‐ylmethylene)‐amino]‐3 H ‐pyrimidin‐4‐one 3a , 3b , 3c , 3d , respectively. IR, 1 H NMR, and 13 C NMR spectra of 3a , 3b , 3c , 3d were given in the experimental section.…”

Design, synthesis, and preliminary evaluation as antimicrobial activity of novel spiro-1, 3-thiazolidine C-acyclic nucleoside analogs

“…The starting materials, 5-hydroxy-4-(D-arabino-1, 2, 3, 4-tetrahydroxybutyl)-thiazolidin-2-thione 3 and 5-acetoxy-4-(D-arabino-1, 2, 3, 4-tetraacetoxybutyl)-thiazolidin-2-thione 4, were prepared according to Jochims et al (25). The hydrazonoyl chloride 1a-f was prepared as the same in the literature (28,29). The biological evaluations of the products were carried out at the Fermentation Biotechnology and Applied Microbiology (Ferm-BAM) Center at Al-Azhar University, Cairo, Egypt.…”