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.