UNEXPECTED TRANSFORMATIONS OF 11-ACETYL-8-BROMO-2-METHYL-5,6-DIHYDRO-2<i>H</i>-2,6-METHANO-1,3,5-BENZOXADIAZOCIN-4(3<i>H</i>)-ONE(THIONE)

Авторы

  • Valentina F. Sedova N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Lavrentiev Ave., Novosibirsk 630090
  • Viktor P. Krivopalov N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Lavrentiev Ave., Novosibirsk 630090
  • Oleg P. Shkurko Новосибирский институт органической химии Сибирского отделения РАН

DOI:

https://doi.org/10.1007/3978

Ключевые слова:

11-acetyl-8-bromo-5, 6-dihydro-2H-2, 6-methano-1, 3, 5-benzoxadiazocin-4(3H)-one, 5-benzoxadiazocine-4(3H)-thione, bromosalicylaldehyde, Biginelli reaction, deacetylation, intramolecular transformation

Аннотация

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 threecomponent 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)-оne(thione). The same methanobenzoxadiazocines underwent deacetylation in boiling ethanol in the presence of HCl.

Биографии авторов

Valentina F. Sedova, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Lavrentiev Ave., Novosibirsk 630090

Laboratory of Heterocyclic Compounds, senior research associate, PhD

Viktor P. Krivopalov, N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Lavrentiev Ave., Novosibirsk 630090

Laboratory of Heterocyclic Compounds, senior research associate

Oleg P. Shkurko, Новосибирский институт органической химии Сибирского отделения РАН

Лаборатория гетероциклических соединений, главный научный сотрудник, д.х.н.

Загрузки

Опубликован

2017-11-29

Выпуск

Том 53 № 10 (2017)

Раздел

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