One-Pot Synthesis of Some New s-Triazole Derivatives and Their Potential Application for Water Decontamination.

A rapid, efficient, and one-pot protocol has been developed for the synthesis of cyclized 2,6-dimethyl-5-substituted-thiazolo[3,2-b]-s-triazoles (3a-c) through the interaction of 5-methyl-1H-s-triazole-3-thiol (1) with aliphatic ketones (2a-d) in refluxing acetic acid in the presence of a catalytic amount of sulfuric acid (AcOH/H+) while with aromatic ketones (5a-d), a mixture of uncyclized 3-methyl-s-triazolylthioacetophenone derivatives (6a-d) and cyclized 6-aryl-2-methyl-thiazolo[3,2-b]-s-triazoles (7a-d) has been produced. With this catalytic system, inexpensive sulfuric acid was utilized as a catalyst, which prevented the production of poisonous and irritating halo carbonyl compounds. On the other hand, the interaction of s-triazole 1 with cyano compounds (9a,b) afforded the corresponding 6-amino-2-methyl-5-substituted-thiazolo[3,2-b]-s-triazoles (10a,b). Similarly, treatment of 4-amino-3-methyl-s-triazole-5-thiol (12) with aliphatic and aromatic ketones (2c and 5a-e) afforded directly 3-methyl-7H-s-triazolo[3,4-b]-1,3,4-thiadiazines (13a and 14a-e). Further, reaction of 12 with cyano compounds (9a,b) under the same reaction conditions yielded the corresponding 3-methyl-s-triazolo[3,4-b]-1,3,4-thiadiazole derivatives (15a,b). The reaction mechanism was studied, and the structures of all novel compounds were verified using spectroscopy and elemental analysis. Moreover, the potential application of the synthesized compounds toward heavy metal ions and inorganic anion removal from aqueous solution has been investigated. The removal effectiveness for metal ions reached up to 76.29%, while for inorganic anions it reached up to 100%, indicating that such synthesized compounds are promising adsorbents for water remediation.

Synthesis of Schiff and Mannich bases of new s-triazole derivatives and their potential applications for removal of heavy metals from aqueous solution and as antimicrobial agents.

An efficient, simple, and one-pot double Mannich reaction was performed for the synthesis of cyclized 2-methyl-6-substituted-6,7-dihydro-5H-s-triazolo[5,1-b]-1,3,5-thiadiazines via a reaction of 5-methyl-1H-s-triazole-3-thiol (1) with formaldehyde and primary aliphatic amines in ethanol at room temperature, while with primary aromatic amines, uncyclized 3-methyl-1-((substituted-amino)methyl)-1H-s-triazole-5-thiols were produced. Under Mannich reaction conditions, 4-amino-3-methyl-s-triazole-5-thiol (8) reacted with formaldehyde only in boiling ethanol or at room temperature to afford 3-methyl-5,6-dihydro-s-triazolo[3,4-b]-1,3,4-thiadiazole without incorporation of secondary amine. Furthermore, after reaction of compound 8 with aromatic aldehydes under different reaction conditions, uncyclized Schiff's bases were produced. Therefore, reaction of these Schiff's bases with primary or secondary amines with formaldehyde in ethanol at room temperature afforded the corresponding Mannich bases 13-14. The structures of all new compounds were confirmed using spectral analysis. Furthermore, most of the synthesized derivatives showed high efficiency for removal of Pb2+, Cd2+, Ca2+, and Mg2+ from aqueous solutions, as well as antimicrobial activity.