Synthesis of 2-Imino-1,3,4-thiadiazoles from Hydrazides and Isothiocyanates via Sequential Oxidation and P(NMe2)3-Mediated Annulation Reactions.,Organic Letters

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Synthesis of 2-Imino-1,3,4-thiadiazoles from Hydrazides and Isothiocyanates via Sequential Oxidation and P(NMe2)3-Mediated Annulation Reactions.
Organic Letters ( IF 4.9 ) Pub Date : 2020-05-10 , DOI: 10.1021/acs.orglett.0c01393
Zhengyan Huang ₁ , Qianqian Zhang ₁ , Qiongli Zhao ₁ , Wenquan Yu ₁ , Junbiao Chang ₁

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A P(NMe₂)₃-mediated annulation reaction of N-acyldiazenes with isothiocyanates, producing 2-imino-1,3,4-thiadiazoles, is reported. This reaction proceeds well with crude N-acyldiazenes derived from the oxidation of hydrazides by iodine and permits the sequential synthesis of products directly from hydrazides without purification of the less stable N-acyldiazene intermediates. The reaction does not require transition metals and is a simple, scalable operation with broad substrate scope.

中文翻译：

由酰肼和异硫氰酸酯通过顺序氧化和P（NMe2）3-介导的环化反应合成2-Imino-1,3,4-噻二唑。

报道了AP（NMe ₂）₃介导的N-酰基二氮烯与异硫氰酸酯的环化反应，产生2-亚氨基-1,3,4-噻二唑。该反应与衍生自酰肼被碘氧化的粗制N-酰基二氮烯进行得很好，并允许直接从酰肼连续合成产物，而无需纯化不稳定的N-酰基二氮烯中间体。该反应不需要过渡金属，是一种简单，可扩展的操作，具有广泛的底物范围。

更新日期：2020-05-10

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