Abstract
1-Aryl-1H-1,2,3-triazole-4-carbonyl chlorides were selected as starting materials for the Boulton–Katritzky rearrangement. When 3-amino-5-methylisoxazole was acylated by 1-aryl-1H-1,2,3-triazole-4-carbonyl chlorides, 1-aryl-5-methyl-N-(5-methylisoxazol-3-yl)-1H-1,2,3-triazole-4-carboxamides 5 were obtained and no further rearrangement occurred. On the other hand, when 1-aryl-1H-1,2,3-triazole-4-carbonyl chlorides were first converted into isothiocyanates by the reaction with KSCN and then were allowed to react with 3-amino-5-methylisoxazole 4 in one pot, intermediate thioureas were formed and spontaneously transformed in statu nascendi into 1,2,4-thiadiazole derivatives 6.GRAPHICAL ABSTRACT
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