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Efficient Synthesis of (2Z,5Z)-3-Benzyl/alkyl-5-(2-oxo-5-aryl-3 (2H)-furanylidene)-2-(phenylimino)-1,3-thiazolidin-4-ones via a One-Pot Three-Component Reaction
Synthesis ( IF 2.2 ) Pub Date : 2024-02-13 , DOI: 10.1055/s-0042-1751557
Abdolali Alizadeh , Reihaneh Moterassed

A simple and efficient strategy for the chemoselective synthesis of (2Z,5Z)-3-benzyl/alkyl-5-(2-oxo-5-arylfuran-3(2H)-ylidene)-2-(phenylimino)thiazolidin-4-one derivatives is developed via a sequential three-component reaction of readily available phenacyl bromides, pyridine and methyl 2-(3-benzyl/alkyl-4-oxo-2-(phenylimino)thiazolidin-5-ylidene)acetates in acetonitrile at room temperature. The advantages of this one-pot sequential Michael addition/1,2-H shift/elimination of pyridine/intramolecular cyclization are highlighted by its low energy requirements (short reaction times at room temperature), excellent yields, the absence of a metal catalyst, and mild conditions. The product structures are characterized by spectroscopic techniques and single-crystal X-ray analysis.



中文翻译:

通过以下方法高效合成 (2Z,5Z)-3-苄基/烷基-5-(2-氧代-5-芳基-3 (2H)-呋喃亚基)-2-(苯基亚氨基)-1,3-噻唑烷-4-酮一锅三组分反应

一种简单有效的化学选择性合成 (2 Z ,5 Z )-3-苄基/烷基-5-(2-氧代-5-芳基呋喃-3(2 H )-亚基)-2-(苯基亚氨基)噻唑烷的策略-4-one 衍生物是通过容易获得的苯甲酰溴、吡啶和 2-(3-benzyl/alkyl-4-oxo-2-(phenimino)thiazolidin-5-ylidene)acetates 在乙腈中的连续三组分反应开发的在室温下。这种一锅顺序迈克尔加成/1,2-H转移/吡啶消除/分子内环化的优点在于其低能量需求(室温下反应时间短)、优异的产率、无需金属催化剂、和温和的条件。通过光谱技术和单晶X射线分析对产品结构进行了表征。

更新日期:2024-02-14
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