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Citation: Qian Pengfei, Wan Huixin, Jiang Jing, Hu Yanwei, Chen Xiaobei, Zhang Shilei. Discovery of a Special Intramolecular Aldol-Like Reaction in the Synthesis of Related Substance E of Tadalafil[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1878-1882. doi: 10.6023/cjoc201602028 shu

Discovery of a Special Intramolecular Aldol-Like Reaction in the Synthesis of Related Substance E of Tadalafil

Qian Pengfei ^a ,
Wan Huixin ^b ,
Jiang Jing ^a ,
Hu Yanwei ^a ,
Chen Xiaobei ^c,*,, ,
Zhang Shilei ^a,*,,

a.
College of Pharmaceutical Science, Soochow University, Suzhou 215123
b.
Central Research Institute of Shanghai Pharmaceuticals Holding Co., Ltd., Shanghai 201203
c.
School of Pharmacy, East China University of Science & Technology, Shanghai 200237

Corresponding author: Chen Xiaobei, xiaobei@ecust.edu.cn Zhang Shilei, zhangshilei@suda.edu.cn
Received Date: 26 February 2016
Revised Date: 12 April 2016

Fund Project: Project supported by the National Natural Science Foundation of China Grant No.21202112Ph.D. Programs Foundation of Ministry of Education of China No. 20123201120019

Figures(5)

In the synthesis of related substance E of tadalafil, a special intramolecular aldol-like reaction was discovered. In this reaction, the α-carbon of ketone attacks the carbonyl group of amide, forming a stable amino hemiketal structure. This reaction can only be realized under the catalysis of silica gel, and other acidic or basic reaction conditions are difficult to obtain the desired product. This finding is a meaningful supplement and extension to aldol reactions.
- aldol reaction,
- amide,
- catalysis on silica gel,
- amino hemiketal,
- related substances of tadalafil
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