Citation: Luo Dayun, Cui Shisheng, Hu Xingmei, Lin Jun, Yan Shengjiao. Synthesis of Amide Class Heterocyclic Ketene Aminals[J]. Chinese Journal of Organic Chemistry, ;2017, 37(1): 166-175. doi: 10.6023/cjoc201607002 shu

Synthesis of Amide Class Heterocyclic Ketene Aminals

Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091

Corresponding author: Lin Jun, linjun@ynu.edu.cn Yan Shengjiao, yansj@ynu.edu.cn
Received Date: 2 July 2016
Revised Date: 25 August 2016

Fund Project: the National Natural Science Foundation of China U1202221the National Natural Science Foundation of China 21662042the National Natural Science Foundation of China 21362042the Talent Found in Yunnan Province 2012HB001the Excellent Young Talents, Yunnan University XT412003

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In this paper, a concise protocol for synthesis of possess potential pharmacological active amide class heterocyclic ketene aminals (HKAs) has been developed, which based on the six or seven-membered HKAs 1~2, using aryl isocyanate 4 as acylation agent.The regioselective acylation reaction of HKAs in 1, 4-dioxane at room temperature gave compounds 5~6 with 90%~98% yields.However, the five-membered HKAs 3 and aryl isocyanate 4 reacted in 1, 4-dioxane catalyzed by Cs₂CO₃ at room temperature to obtain compounds 7 in 78%~93% yields.
- heterocyclic ketene aminals,
- isocyanate,
- regioselective,
- acylation reaction
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