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

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

Journal

Chemistry of Heterocyclic Compounds
ISSN: 0009-3122 , E-ISSN: 1573-8353

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

Authors

Sedova Valentina F. ¹ , Krivopalov Viktor P. ¹ , Shkurko Oleg P. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, 9 Lavrentiev Ave, Novosibirsk 630090, Russia

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.

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

Published print:	Oct 1, 2017
Published online:	Dec 5, 2017

Web of science	WOS:000417584000018
Scopus	2-s2.0-85036569991
Elibrary	35512890
OpenAlex	W2773000939