Synthetic modifications of carboline alkaloid harmine: synthesis of 8-substituted derivatives

被引：0
|
作者：
Sergazy M. Adekenov
Pernesh Zh. Zhanimkhanova
Zhangeldy S. Nurmaganbetov
Asel Amanzhan
Sergey V. Chernov
Aibek Zh. Turmukhambetov
Irina Yu. Bagryanskaya
Yurii V. Gatilov
Elvira E. Shults
机构：
[1] JSC International Research and Production Holding “Phytochemistry”,N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
[2] Siberian Branch of the Russian Academy of Sciences,undefined
[3] Novosibirsk State University,undefined
来源：
Chemistry of Heterocyclic Compounds | 2019年 / 55卷
关键词：
8-acetylharmine; β-carbolines; chalcones; 8-formylharmine; pyrazolines; X-ray structural analysis;
D O I：
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学科分类号：
摘要：
Hybrid molecules containing β-carboline and 1-acetylpyrazoline moieties were obtained on the basis of the alkaloid harmine. The synthetic procedure included acetylation of harmine with acetyl chloride in the presence of tin(IV) chloride, Claisen–Schmidt condensation with benzaldehydes under basic conditions, and cyclization of the obtained chalcones by the action of hydrazine hydrate and acetic acid. In addition, a method was proposed for the preparation of 8-formylharmine by treating harmine with dichloromethoxymethane in the presence of tin(IV) chloride. The structures of the synthesized compounds were confirmed by NMR spectra, mass spectra, and X-ray structural analysis.
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页码：135 / 141
页数：6
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