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

Chemistry of Heterocyclic Compounds Aims and scope

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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The work was supported by FASO Russia on the project 0302-2016-0001.

Mass spectra, IR and NMR spectra were recorded at the Chemical Service Center of the SB RAS.

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Correspondence to Oleg P. Shkurko.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1163–1166

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Sedova, V.F., Krivopalov, V.P. & Shkurko, O.P. Unexpected transformations of 11-acetyl-8-bromo-2-methyl-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one(thione). Chem Heterocycl Comp 53, 1163–1166 (2017). https://doi.org/10.1007/s10593-017-2187-5

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