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)

Authors

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

DOI:

https://doi.org/10.1007/3978

Keywords:

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

Abstract

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.

Author Biographies

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, 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, Chief researcher, Doctor of Chemistry

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Published

2017-11-29

Issue

Vol. 53 No. 10 (2017)

Section

Short Communications