Abstract
A novel efficient three-component annelation of the thiadiazinyl ring onto 4-amino-4H-[1, 2, 4]triazole-3-thiol, catalyzed by nontoxic, recyclable InCl3 under microwave activation, has been developed. The transformation of 4-amino-5-aryl-4H-[1, 2, 4]triazole-3-thiol into triazolothiadiazine involves chemoselective successive double addition reaction consisting of an InCl3-catalyzed dehydrative nucleophilic addition of amino group to an aromatic aldehyde followed by addition of the resulting Schiff base to cyclohexyl isocyanide. The intramolecular cyclization of the adduct results in 3,6-diaryl-5H-[1, 2, 4]triazolo[3,4-b][1, 3, 4]thiadiazine. The reaction proceeds smoothly with good yields.
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