Unexpected transformations of 11-acetyl-8-bromo-2-methyl-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one(thione)

被引：0
|
作者：
Valentina F. Sedova
Viktor P. Krivopalov
Oleg P. Shkurko
机构：
[1] Siberian Branch of the Russian Academy of Sciences,N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry
来源：
Chemistry of Heterocyclic Compounds | 2017年 / 53卷
关键词：
11-acetyl-8-bromo-5,6-dihydro-2; -2,6-methano-1,3,5-benzoxadiazocin-4(3; )-one; 11-acetyl-8-bromo-5,6-dihydro-2; 2,6-methano-1,3,5-benzoxadiazocine-4(3; )-thione; bromosalicylaldehyde; Biginelli reaction; deacetylation; intramolecular transformation;
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学科分类号：
摘要：
11-Acetyl-8-bromo-2-methyl-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one and -4(3H)-thione are prepared via the three-component Biginelli condensation as the only diastereomers. For the first time we observed that these compounds in DMSO solution undergo a slow isomerization with formation of mixtures with the respective 4-(5-bromo-2-hydroxyphenyl)-3,4-dihydropyrimidin-2(1Н)-one(thione). The same methanobenzoxadiazocines underwent deacetylation in boiling ethanol in the presence of HCl.
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页码：1163 / 1166
页数：3
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