A study of the alkylation and acylation of N-acylthiazolidinethione

作者：Su H; Yang J H; Lu C F; Chen Z X; Yang G C^*

来源：Indian Journal of Chemistry - Section B: Organic and Medicinal Chemistry , 2013, 52(6): 769-775.

• Alkylation
• acylation
• N-acylthiazolidinethione
• enolate
• decomposition

Investigating the alkylation and acylation of N-acylthiazolidinethione, the desired a-alkylated products and C-acylated products are not obtained, but rather the S-alkylated products and O-acylated products are obtained. The possible mechanism proposed shows that the deprotonation agent and electrophilic species are responsible for the stability of enolates. The enolates derived from N-acylthiazolidinethiones are decomposed in the presence of base, but they are comparatively stable in the presence of Lewis acid. When electrophilic reagent is alkyl halide, the enolate decomposition is the dominating pathway, and affords the S-alkylated products; and when electrophilic reagent is acyl chloride, the formation of a highly ordered chelated transition-state is the dominating pathway, and affords the O-acylated products.

• 出版日期2013-6
• 单位湖北大学