Syntheses and Biological Activities of 6-Aryl-3-(3-hydroxy- propyl)-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines

Abstract

A series of 6-aryl-3-(3-hydroxypropyl)-7H-1,2,4-triazolo [3,4-b][1,3,4]-thiadiazines were synthesized by the reaction of 4-amino-3-(3-hydroxypropyl)-5-mercapto-1,2,4-triazole (1) with substituted ω-haloacetophenones. Their structures were confirmed by elemental analysis, IR, 1 H-NMR, and 13 C-NMR. Tests of plant growth regulating effects showed that the title compounds display remarkable inhibitory activities on the growth of radish and wheat.

Vision on Synthetic and Medicinal Facets of 1,2,4-Triazolo[3,4-b][1,3,4]thiadiazine Scaffold

“…However, this method has limited substrate scope. Route b involves the cyclocondensation of 4-amino-3-mercaptotriazoles with various bielectrophiles such as α-bromopropenone [ 3 ], phenacyl bromides [ 4 – 8 ], α-tosyloxy ketones [ 9 ], ethyl bromoacetate [ 10 ], hydrazonoyl halides [ 11 ], α-chloroacetylacetone [ 12 ] and propargyl bromide in presence of heteropolyacids [ 13 ] under conventional heating conditions to access the triazolothiadiazine scaffold. This can be credited to mercapto and amino groups as easily accessible nucleophilic centers in 4-amino-3-mercaptotriazole for the synthesis of condensed heterocyclic rings.…”

Synthesis of triazolo-thiadiazine and their derivatives by hydrazine hydrate, thiocarbohydrazine and thiosemicarbazide: A review

“…Figure 5: According to Jian et al[17] there areseveral 6aryl-3-(3-hydroxypropyl)-7H-1,2,4-triazolo [3,4-b] [1,3,4] thiadiazines were synthesised by reacting 4-amino-3-(3hydroxypropyl)-5-mercapto-1,2,4-triazole with substituted…”

Synthesis and Biological Activity of Some Novel Derivatives of 4-Amino-3-(D-galactopentitol-1-yl)-5-mercapto-1,2,4-triazole

“…Prompted by these observations and as a continuation of the success of the attachment of a hydroxypropyl group to the 3-position [9], we have now synthesized a series of 6-aryl-3-(D-galactopentitol-1-yl)-7H-1,2,4-triazolo [3,4-b] [1,3,4]thiadiazines and 4-(arylmethylidene)amino-5-(D-galactopentitol-1-yl)-3-mercapto-4H-1,2,4-triazoles, then confirmed their structures by elemental analysis, IR, 1 H-and 13 C-NMR, and determined the plant growth regulating effects of all the title compounds and the key intermediate 1.…”