1.2.4- Triazoline-3-thiones 1.2.4- triazoles

Triazoline thiones can be converted to the corresponding triazoles with Raney nickel, nitric acid and hydrogen peroxide <75LA1264>. Sulfoxides can be obtained by controlled treatment with... 

Recently a novel member of the meso-ionic class of l,2,4-triazole-3-thiones (227) has been described. Heating the sodium salt, Ph-CO-NPh-NH-CS—S-CHj—COjNa, with hydrazine gave the compound 227, R = R = Ph, R = NHj, which was characterized as a monobenzylidene derivative. The meso-ionic hydrazine derivative 227, R = R = Ph, R = NHj, undergoes an interesting reaction with nitrous acid, yielding the l,2,4-triazoline-3-thione (239). ... 

Reaction of thio- and alkylthio derivatives of A -aminoazoles with aryl isothiocyanates leads to annelation of a 1,3,4-thiadiazole or a 1,2,4-triazole ring. Thus, 4-amino-3-methyl-l,2,4-triazoline-5-thione, on reaction with aryl isothiocyanates under mild conditions, gives products of addition (388), which on heating are transformed to 2-arylaminotriazolo[3,4-/>]thia-diazoles (389) (83S411 87JHC1173). 

The use of diarylcarbodiimides as bifunctional amphoteric synthons also leads to annelation of the 1,2,4-triazoles ring. A typical example is the conversion of 2V-aminoimidazole 392 to imidazo[l, 2-b]triazoles 393 (88H161). Similarly, triazolo[4,3-Z>]triazoles 394 have been synthesized from 4-amino-i-triazoline-5-thiones [68JCS(C)2099 88H161]. 

Ch. 12 1,2,4-Triazoles Containing More lhan One Representative Function Ch. 13 Alkyl- or Aryl-l,2,4-triazolin-5-ones Ch. 14 Alkyl- or Aryl-1,2,4 triazohne-5-thiones... 

Photochemical desulfuration 1,2,4-Triazoles from l,2,4-triazoline-3-thiones... 

C3HaNi,OS, 4-Formylamino-A -l, 2,4-triazoline-5-thione, 45B, 196 C3H5N5O, 5-Amino-lH-1,2,3-triazole-4-carboxamide, 40B, 196 C3H6N2S, Ethylenethiourea, 17, 745... 

The ami nolysis of substituted 4-ary lazo-A -thiazolin-5-ones has been investigated, with the results shown in Scheme 3. Treatment of 2-alkoxy-4-arylazo-A -thiazolin-5-ones (153) with strongly basic amines yields, depending on the nature of the 2-alkyloxy-groups [in (153)], the l,2,4-triazolin-5-ones (156) or -5-thiones (155). Aromatic amines yield the 1,2,4-triazoles (154). Probable common intermediate stages of these reactions are shown. ... 

Amino-5-thioxo-l,2,4-triazolidin-3-one 3-hydrazone, 9CI. 4-Amino-5-hydrazino-4H-1,2,4-triazole-3-thiol, SCI. 4-Amino-3-hydrazino-1,2,4-triazoline-5-thione. Purpald [1750-12-5]... 

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