SYNTHESIS AND PROPERTIES OF <i>Z</i>-1,3-BIS-(ARYL)-4-BROMO-2-BUTEN-1-ONES
DOI:
https://doi.org/10.1007/6553Keywords:
2, 4-bis(aryl)thiophene, 4-bis(aryl)furan, γ-bromodypnone, α-bromodiphenacyl, 1, 3, 5-triaryl-1, 6-dihydropyridazineAbstract
Bromination of 1,3-bis(aryl)-2-buten-1-ones by N-bromosuccinimide in anhydrous carbon tetrachloride gives Z-1,3-bis(aryl)-4-bromo-2-buten-1-ones. The effect of the nature of substituent in the benzene ring on the course of a reaction with nucleophiles has been studied. Heating an alcohol solution of these ketones (Ar = 4-MeOC6H4, 4-ClC6H4) in the presence of acid or in the presence of base (Ar = Ph) gave 2,4-bis(aryl)furans. Treatment of 1,3-bis(aryl)-4-bromo-2-buten-1-ones with thioacetamide gave 2,4-bis(aryl)thiophenes. The oxidation of the halo-substituted dypnones with H2O2/NaOH gave (3-bromomethyl-3-aryl-2-oxiranyl)(aryl)methanones. The reaction of halo-substituted dypnones with aryl hydrazines gave 1,3,5-triaryl-1,6-dihydropyridazines or 1,3,5-triarylpyridazinium bromides depending on the structure of the reagents.
How to Cite
Potikha, L. M.; Turelik, A. R.; Kovtunenko, V. A. Chem. Heterocycl. Compd. 2009, 45, 1184. [Khim. Geterotsikl. Soedin. 2009, 1478.]
For this article in the English edition see DOI 10.1007/s10593-010-0405-5
