Chinese Journal of Organic Chemistry >
Discovery of a Special Intramolecular Aldol-Like Reaction in the Synthesis of Related Substance E of Tadalafil
Received date: 2016-02-26
Revised date: 2016-04-12
Online published: 2016-04-20
Supported by
Project supported by the National Natural Science Foundation of China (Grant No.21202112), Ph.D. Programs Foundation of Ministry of Education of China (No. 20123201120019) and PAPD (A Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions).
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.
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
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