One-Pot Double Oxidation Synthesis of N-1-Piperidonyl Amides From N-1-Piperidinyl Amides with meta-Chloroperbenzoic Acid: Rimonabant Analogue as Model Study

被引：0
|
作者：
Chen, Yu-Chieh [1 ]
Zeng, Wei-Zheng [2 ]
Li, Sin-Min [3 ]
Chou, Jia-Yu [4 ]
Tsai, Shuo-En [1 ]
Fuh Wong, Fung [1 ]
机构：
[1] China Med Univ, Sch Pharm, 100 Jingmao 1st Rd, Taichung 406040, Taiwan
[2] China Med Univ, Dept Nutr, 100 Jingmao 1st Rd, Taichung 406040, Taiwan
[3] China Med Univ, Inst Translat Med & New Drug Dev, 91 Hsueh Shih Rd, Taichung 40402, Taiwan
[4] China Med Univ, Master Program Pharmaceut Manufacture, 100 Jingmao 1st Rd, Taichung 406040, Taiwan
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 45期
关键词：
mCPBA; N-1-piperidinyl amide; N-1-piperidonyl amide; oxidation; Rimonabant analogues; PHARMACOLOGICAL EVALUATION; EPOXIDATION; DESIGN; METABOLITES; CATALYSIS; COMPLEX; KETONES; MCPBA; FINE;
D O I：
10.1002/chem.202300702
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A simple and efficient one-pot oxidation synthesis of N-1-piperidonyl amides was successfully developed through the double oxidation of hydrazides (involving hydrazonium formation, azodioxy-carbonyl compounds generation, and & alpha;-carbon oxidation) by using meta-chloroperbenzoic acid (mCPBA). The convenient oxidation method was also extended to Rimonabant analogue. The lactam oxidized Rimonabant analogue was first successfully synthesized for demonstrating the construction and characterized by NMR spectroscopic methods and the single-crystal X-ray diffraction study (ORTEP).
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页数：6
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