Novel Rearrangement of 5-Arylazo-2-thiohydantoin Derivatives with Alkali and Aromatic Amines

Abstract

<jats:title>Abstract</jats:title><jats:p> 5-Arylazo-2-thiohydantoin derivatives (2a,c) were cleaved and rearranged by aqueous sodium hydroxide to give the corresponding 1-aryl-⊿<jats:sup>2</jats:sup>-1,2,4-trazole-5-imino-3-carboxylic acids (3a-c). 3 a was decarboxylated to 1-phenyl-⊿<jats:sup>2</jats:sup> -1,2,4-triazoline-5-imine (5). Hydrolysis of 5-arylazo-1-phenyl-2-thiohydantoins (6a-c) behaved in different manner affording 1-aryl-4-phenyl-⊿<jats:sup>2</jats:sup> -1,2,4-triazoline-5-thione-3-carboxylic acids (7a-c). Fusing (2a-c) with aromatic amines at high temperature gave the corresponding anilides (8a-h). Treatment of 5-arylidene-2-thiohydantoin derivatives (9a-c) with hydrazine hydrate gave colourless products of thioureido cinnamic acid hydrazide derivatives (10a-c), while refluxing 5-arylidene-2-methylmercaptohydantoin (11a-d) with hydrazine hydrate and/or benzo-phenone hydrazone gave the corresponding glycocyamidine derivatives (12a-g).</jats:p>

A Novel Synthesis of Some New Imidazothiazole and Glycocyamidine Derivatives and Studies on Their Antimicrobial Activities

“…Apparently, the increased electrophilicity of this carbon atom is due to the presence of the 3-phenyl group 18 (in cases where there are no such 3-aryl substituents, no such rearrangements have been reported) 19,20 Intermediates 9a,b may undergo ring closure according to two possible pathways, A and B (Scheme 2).…”

Synthesis, theoretical investigation, ADMET studies, antimicrobial activity, and docking analysis of some novel imidazolidinone derivatives

“…The silica gel (0.040 -0.063 mm) was used for the column chromatography and was purchased from Merck. 5-Arylidene-2-methylthiohydantoins 2a-c were synthesized according to the previously published method 46 . Different techniques were used to confirm the formation of 1a-c and the structures of compounds 1a-c are not similar to that reported previously [46].…”

Synthesis of Novel Derivatives of Imidazo[2,1-c][1,2,4]Triazine from Biologically Active 4-Arylidene-2-Hydrazino-1-Phenyl-1H-Imidazol-5(4H)-Ones and Evaluation of their Antimicrobial Activity

“…The starting compounds 6a-c were synthesised by heating 4-arylidine-2-(methylthio)-1-phenyl-1H-imidazolidin-5(4H)-ones 5a-c 21,22 with hydrazine hydrate in ethanol for 1h, adopting the reported methods. 23,24 4-Aryl-6-arylidine-8-phenyl-6,8-dihydroimidazo[2,1-c] [1,2,4]triazin-7(2H)-ones 4a-n were obtained via the reaction of compounds 6a or 6b with various phenacyl bromide derivatives in refluxing DMF containing anhydrous potassium carbonate for 72 h. 25,26 The isolated compounds, after pouring into cold water, filtration and crystallisation, were subjected to spectroscopic and elemental analysis. IR spectroscopy showed the presence of the NH band in the 3435-3280 cm -1 range and Scheme 1 Synthesis of target compounds.…”