Efficient and Practical Route to α‐Aminocarbonylketene and α‐Cyanoketene Dithioacetals

Abstract

An efficient and practical route to α‐aminocarbonylketene dithioacetals 5 and α‐cyanoketene dithioacetals 6 was developed. With readily available α‐acetyl‐α‐aminocarbonyl ketene dithioacetals 4 as the starting materials, α‐aminocarbonylketene dithioacetals 5 were prepared in high yield via base‐catalyzed (sodium hydroxide) deacetylation. In the presence of POCl₃ and with DMF as the solvent, α‐cyanoketene dithioacetals 6 were obtained via dehydration of 5 in excellent yield.

Keywords:

• α‐acetyl‐α‐aminocarbonyl ketene dithioacetals
• α‐aminocarbonylketene
• α‐cyanoketene dithioacetals
• deacetylation
• dehydration
• dithioacetals

Acknowledgments

Financial support of this by the National Natural Science Foundation of China (NNSFC) (20272008) and the Key Grant Project of Chinese Ministry of Education (10412) are greatly acknowledged.