由溴化间苯重复单元组成的环六酰胺的合成

IF 1.5 4区医学 Q4 CHEMISTRY, MEDICINAL

Chemical & pharmaceutical bulletin Pub Date : 2024-03-08 DOI:10.1248/cpb.c24-00023

Akihiro Yokoyama, Ayaka Chino, Kenta Rakumitsu

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引用次数: 0

摘要

为了合成环己酰胺，4-溴-3-(异丁基氨基)苯甲酸在 1,1,2,2- 四氯乙烷中的二氯三苯基膦或吡啶中的四氯硅烷存在下进行了自缩合反应。然而，得到的不是目标环六酰胺，而是环三酰胺和环四酰胺。环六酰胺是通过二聚体的自缩合成功合成的，二聚体是由 4-溴-3-（异丁氨基）苯甲酸分五步合成的。为了提高目标大环的产率，对自缩合条件进行了全面筛选。此外，还通过分步脱保护和缩合合成了线性六聚体，并以良好的收率环化得到了环状六酰胺。

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Synthesis of a Cyclic Hexaamide Consisting of a Brominated m-Phenylene Repeating Unit

Aiming to synthesize a cyclic hexaamide, 4-bromo-3-(isobutylamino)benzoic acid was subjected to self-condensation reactions in the presence of either dichlorotriphenylphosphorane in 1,1,2,2-tetrachloroethane or tetrachlorosilane in pyridine. However, instead of the targeted cyclic hexaamide, the cyclic triamide and the cyclic tetraamide were obtained. The cyclic hexaamide was successfully synthesized via the self-condensation of the dimer, which was synthesized in five steps from 4-bromo-3-(isobutylamino)benzoic acid. A thorough screening of the self-condensation conditions was performed to improve the yield of the target macrocycle. In addition, the linear hexamer was synthesized by stepwise deprotection and condensation, and its cyclization afforded the cyclic hexaamide in good yield.

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来源期刊

Chemical & pharmaceutical bulletin 医学-化学综合

CiteScore

3.20

自引率

5.90%

发文量

132

审稿时长

1.7 months

期刊介绍： The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below. Topics: Organic chemistry In silico science Inorganic chemistry Pharmacognosy Health statistics Forensic science Biochemistry Pharmacology Pharmaceutical care and science Medicinal chemistry Analytical chemistry Physical pharmacy Natural product chemistry Toxicology Environmental science Molecular and cellular biology Biopharmacy and pharmacokinetics Pharmaceutical education Chemical biology Physical chemistry Pharmaceutical engineering Epidemiology Hygiene Regulatory science Immunology and microbiology Clinical pharmacy Miscellaneous.