A Convenient Synthesis of Tetrasubstituted Pyrazoles from Nitrile Imines and 2-(Thioxothiazolidin-5-ylidene)acetates,Synlett

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A Convenient Synthesis of Tetrasubstituted Pyrazoles from Nitrile Imines and 2-(Thioxothiazolidin-5-ylidene)acetates
Synlett ( IF 1.7 ) Pub Date : 2018-02-27 , DOI: 10.1055/s-0036-1591921
Issa Yavari ₁ , Zohreh Taheri ₁ , Maryam Naeimabadi ₁ , Samira Bahemmat ₂ , Mohammad Halvagar ₂

Affiliation

Alkyl 2-(3-alkyl-4-oxo-2-thioxothiazolidin-5-ylidene)acetates react with hydrazonoyl chlorides in the presence of triethylamine to afford tetrasubstituted pyrazole derivatives. Formally, this transformation is regarded as a 1,3-dipolar cycloaddition of the exocyclic carbon–carbon double bond of the thioxothiazolidine derivatives with nitrile imines generated in situ. This efficient method provides fast access to a range of structurally diverse pyrazoles. The structure of a typical product is confirmed by X-ray crystallography.

中文翻译：

由腈亚胺和 2-(Thioxothiazolidin-5-ylidene) 乙酸盐方便地合成四取代的吡唑

2-(3-烷基-4-氧代-2-硫代噻唑烷-5-亚基)乙酸烷基酯在三乙胺存在下与腙酰氯反应，得到四取代的吡唑衍生物。形式上，这种转变被认为是硫代噻唑烷衍生物的环外碳-碳双键与原位生成的腈亚胺的 1,3-偶极环加成。这种有效的方法提供了对一系列结构不同的吡唑的快速访问。典型产品的结构由 X 射线晶体学证实。

更新日期：2018-02-27

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