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- Title
Unexpected transformations of 11-acetyl-8-bromo-2-methyl-5,6-dihydro-2 H-2,6-methano-1,3,5-benzoxadiazocin-4(3 H)-one(thione).
- Authors
Sedova, Valentina; Krivopalov, Viktor; Shkurko, Oleg
- Abstract
11-Acetyl-8-bromo-2-methyl-5,6-dihydro-2 H-2,6-methano-1,3,5-benzoxadiazocin-4(3 H)-one and -4(3 H)-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(1 Н)-one(thione). The same methanobenzoxadiazocines underwent deacetylation in boiling ethanol in the presence of HCl.
- Subjects
DIASTEREOISOMERS; THIONES; ISOMERIZATION; ETHANOL; CONDENSATION
- Publication
Chemistry of Heterocyclic Compounds, 2017, Vol 53, Issue 10, p1163
- ISSN
0009-3122
- Publication type
Article
- DOI
10.1007/s10593-017-2187-5