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4-氯香豆素-3-磺酰氯的改进合成方法及其与不同双齿亲核试剂的反应，以生成吡啶并[1',2':2,3]-和噻嗪并[3',2':2,3]-1,2,4-噻二嗪并[6,5-c]苯并吡喃-6-酮7,7-二氧化物。

An improved synthesis of 4-chlorocoumarin-3-sulfonyl chloride and its reactions with different bidentate nucleophiles to give pyrido[1',2':2,3]- and thiazino[3',2':2,3]-1,2,4-thiadiazino[6,5-c]benzopyran-6-one 7,7-dioxides.

作者信息

Jashari Ahmed, Hey-Hawkins Evamarie, Mikhova Bozhana, Draeger Gerald, Popovski Emil

机构信息

Group of Physics and Chemistry, Faculty of Natural Sciences and Mathematics, State University of Tetova, 1200 Tetova, Macedonia.

出版信息

Molecules. 2007 Aug 22;12(8):2017-28. doi: 10.3390/12082017.

DOI:10.3390/12082017
PMID:17960102
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6149111/
Abstract

An improved synthetic method affording 4-chlorocoumarin-3-sulfonyl chloride (4) in very good yield (ca. 85%) is reported. This compound was reacted with various bidentate nucleophiles such as 2-aminopyridines and 2-aminothiazoles in order to obtain substituted pyrido- and thiazino-1,2,4-thiadiazino-benzopyranone dioxides (potential anticancer and anti-HIV agents). These reactions occurred rapidly at room temperature giving yellowish precipitates, which are insoluble in common organic solvents, making the purification process challenging. Further investigation has shown that these fused heterocycles are not stable and decompose with opening of the 1,2,4-thiadiazine ring.

摘要

报道了一种改进的合成方法，该方法能以非常高的产率（约85%）得到4-氯香豆素-3-磺酰氯（4）。该化合物与各种双齿亲核试剂如2-氨基吡啶和2-氨基噻唑反应，以获得取代的吡啶并和噻嗪并-1,2,4-噻二嗪并苯并吡喃二酮（潜在的抗癌和抗HIV药物）。这些反应在室温下迅速发生，生成淡黄色沉淀，这些沉淀不溶于常见的有机溶剂，这使得纯化过程具有挑战性。进一步的研究表明，这些稠合杂环不稳定，会随着1,2,4-噻二嗪环的开环而分解。

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