Nonionic surfactants have emerged as an important new class of organic compounds. They are well known for their chemotherapeutic properties as antiviral, anticancer, antifungal and antibacterial agents. Structural modifications improve their industrial and biological applications. The 1,2,4-triazole nucleus is a bioactive scaffold with significant chemotherapeutic characteristics, including antioxidant, anticonvulsant, antitumor, antidepressant, antiparasitic and antimicrobial activities. Ultrasound (US) techniques have gained an outstanding status in organic synthesis due to reduction in reaction time, yield enhancement and cleaner chemistry. Only a few examples have been reported in the literature on the synthesis of surfactants with clubbed triazole cores. We now report the ultrasound assisted synthesis of new Sand S,N-bis(nonionic) surfactants derived from 5-(2,3-chlorophenyl)-2,4-dihydro-1,2,4-triazole-3-thione (3). Based on a modified literature method, the key intermediate 3 has been obtained via multi-step synthesis as described in Scheme 1. The condensation of 2,3dichlorobenzoyl chloride (1) with thiosemicarbazide in dry acetone under reflux for 4 h afforded the corresponding acylthiosemicarbazide 2 in good yield (85%). Shorter time (1min) was consumed when the condensation of the acid chloride 1 with thiosemicarbazide was assisted by ultrasound irradiation and gave the corresponding acylthiosemicarbazide 2 in excellent yield (98%). Intramolecular ring closure of the resulting thiosemicarbazide derivative 2 in refluxing 10% NaOH solution for 6 h furnished the target 5-(2,3-chlorophenyl)-2,4-dihydro-1,2,4-triazole-3-thione (3) in 80% yield. Great reduction (3min) in the time of dehydrative cyclization of 2 was observed under ultrasound irradiation and the target 1,2,4-triazole-3-thione 3a was obtained in 97% yield.

中文翻译：

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新型棒状1,2,4-三唑类化合物的制备及抗菌评价

非离子表面活性剂已成为一类重要的新型有机化合物。它们以其作为抗病毒、抗癌、抗真菌和抗菌剂的化学治疗特性而闻名。结构修饰改善了它们的工业和生物应用。1,2,4-三唑核是一种生物活性支架，具有显着的化疗特性，包括抗氧化、抗惊厥、抗肿瘤、抗抑郁、抗寄生虫和抗菌活性。由于反应时间的减少、产量的提高和更清洁的化学反应，超声波 (US) 技术在有机合成中获得了突出的地位。文献中仅报道了几个关于合成具有棒状三唑核的表面活性剂的例子。我们现在报告新 Sand S 的超声辅助合成，衍生自 5-(2,3-氯苯基)-2,4-二氢-1,2,4-三唑-3-硫酮 (3) 的 N-双（非离子）表面活性剂。基于改进的文献方法，通过多步合成获得了关键中间体 3，如方案 1 所述。 2,3-二氯苯甲酰氯 (1) 与氨基硫脲在无水丙酮中回流缩合 4 小时，得到相应的酰氨基脲2良率 (85%)。当酰氯 1 与氨基硫脲在超声照射的辅助下缩合时，消耗的时间更短（1 分钟），并以极好的收率（98%）得到相应的酰氨基硫脲 2。所得氨基硫脲衍生物 2 在 10% NaOH 溶液回流 6 小时后发生分子内闭环，得到目标 5-(2,3-氯苯基)-2,4-二氢-1,2,4-三唑-3-硫酮 (3 ) 80% 的收率。