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

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...

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Published inChemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 53; no. 10; pp. 1163 - 1166
Main Authors Sedova, Valentina F., Krivopalov, Viktor P., Shkurko, Oleg P.
Format Journal Article
LanguageEnglish
Published New York Springer US 01.10.2017
Springer Nature
Springer Nature B.V
Subjects
Chemistry
Chemistry and Materials Science
Chemistry, Organic
Ethanol
Isomerization
Organic Chemistry
Pharmacy
Physical Sciences
Science & Technology
2,6-methano-1,3,5-benzoxadiazocin-4
2,6-methano-1,3,5-benzoxadiazocine-4
deacetylation
one
Biginelli reaction
bromosalicylaldehyde
11-acetyl-8-bromo-5,6-dihydro-2
thione
intramolecular transformation
11-acetyl-8-bromo-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one
BIGINELLI-LIKE REACTION
ONE-POT SYNTHESIS
TETRAHYDROPYRIMIDINES
11-acetyl-8-bromo-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocine-4(3H)-thione
SALICYLALDEHYDE
CATALYST
DERIVATIVES
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-017-2187-5