Efficient, One-Pot Synthesis of Triazolothiadiazinyl-pyrazolone and Pyrazolyl-triazolothiadiazine Derivatives via Multicomponent Reaction

A one-pot, multicomponent reaction of 3-(2-bromo acetyl)coumarins, 4-amino-5-hydrazino-4H-[1,2,4]triazole-3-thiol, and different derivatives of ethyl 2-(2-(aryl)hydrazono)-3-oxobutanoates provide an efficient and direct method for the synthesis of 4-(arylydrazono)-3-methyl-1-(6-(coumarin-3-yl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-1H-pyrazol-5(4H)-ones (<b>4a–h</b>). A similar methodology was also developed for the synthesis of pyrazolyl-triazolothiadiazines (<b>9a–f</b>) using acetyl acetone, 4-amino-5-hydrazino-4H-[1,2,4]triazole-3-thiol, and different derivatives of phenacylbromide. The resulting products were characterized by analytical and spectral data.

以3-(2-溴乙酰基)香豆素、4-氨基-5-肼基-4H-[1,2,4]三唑-3-硫醇以及2-(2-芳基腙基)-3-氧代丁酸乙酯的不同衍生物为原料，通过一锅多组分反应，可高效直接合成4-(芳基腙基)-3-甲基-1-(6-(香豆素-3-基)-7H-[1,2,4]三唑并[3,4-b][1,3,4]噻二嗪-3-基)-1H-吡唑-5(4H)-酮类化合物（<b>4a–h</b>）。采用乙酰丙酮、4-氨基-5-肼基-4H-[1,2,4]三唑-3-硫醇与苯甲酰溴的不同衍生物，通过相似的反应策略同样可合成吡唑基三唑并噻二嗪类化合物（<b>9a–f</b>）。所得产物均通过分析测试与波谱数据完成了结构表征。