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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)

Valentina F. Sedova, Viktor P. Krivopalov, Oleg P. Shkurko
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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.


Keywords


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

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