Unexpected transformations of 11-acetyl-8-bromo-2-methyl-5,6-dihydro-2H-2,6-methano-1,3,5-benzoxadiazocin-4(3H)-one(thione) Full article
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Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353 |
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| Output data | Year: 2017, Volume: 53, Number: 10, Pages: 1163-1166 Pages count : 4 DOI: 10.1007/s10593-017-2187-5 | ||
| Tags | 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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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 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(1De)-one(thione). The same methanobenzoxadiazocines underwent deacetylation in boiling ethanol in the presence of HCl.
Cite:
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)
Chemistry of Heterocyclic Compounds. 2017. V.53. N10. P.1163-1166. DOI: 10.1007/s10593-017-2187-5 WOS Scopus РИНЦ OpenAlex
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. 2017. V.53. N10. P.1163-1166. DOI: 10.1007/s10593-017-2187-5 WOS Scopus РИНЦ OpenAlex
Dates:
| Published print: | Oct 1, 2017 |
| Published online: | Dec 5, 2017 |
Identifiers:
| Web of science: | WOS:000417584000018 |
| Scopus: | 2-s2.0-85036569991 |
| Elibrary: | 35512890 |
| OpenAlex: | W2773000939 |