16339-93-8Relevant academic research and scientific papers
Synthesis of new 1,4- and 1,5-disubstituted N-ethyl acetate and N-α-butyro-γ-lactone alkylimidazole derivatives as N-acylhomoserine lactone analogs
Zhang, Qiang,Li, Si-Zhe,Queneau, Yves,Soulère, Laurent
, p. 2298 - 2303 (2021/09/16)
New alkylimidazoles functionalized with a homoserine lactone or an alkyloxycarbonyl moiety have been synthesized as N-acylhomoserine lactones (AHLs) analogs. The 1,4-disubstituted imidazole derivatives were prepared by alkylation of 4(5)-alkylimidazoles with α-bromo-γ-butyrolactone or ethyl α-bromoacetate. An alternative route was preferred for the synthesis of their 1,5-disubstituted counterparts based on the use of a N1-protected alkylimidazole, its alkylation to an N3-imidazolyl-α-acetate and deprotection to the desired 1,5-disubstituted esters and subsequent alkylation of the acetate moiety with cyclic ethylene sulfate followed by acid-catalyzed cyclization. The ability to modulate bacterial quorum sensing of all new compounds was compared to that of previously reported AHL analogs in which the amide bond is replaced by a heterocyclic group.
Variation in the regioselectivity of levulinic acid bromination in ionic liquids
Zavozin, Alexander G.,Kravchenko, Natalya E.,Ignat'ev, Nikolay V.,Zlotin, Sergei G.
scheme or table, p. 545 - 547 (2010/10/02)
The reaction of levulinic acid and its esters with bromine in ionic liquids results in the formation of 3-bromo derivatives as the major products and not the 5-bromo substituted isomers, which are typically formed in organic solvents. The bromination of l
A mild and efficient procedure for α-bromination of ketones using N-bromosuccinimide catalysed by ammonium acetate
Tanemura, Kiyoshi,Suzuki, Tsuneo,Nishida, Yoko,Satsumabayashi, Koko,Horaguchi, Takaaki
, p. 470 - 471 (2007/10/03)
Cyclic ketones reacted with N-bromosuccinimide (NBS) catalysed by NH 4OAc in Et2O at 25°C to give the corresponding α-brominated ketones in good yields, while acyclic ketones were efficiently brominated in CCl4 at 80°C.
SYNTHESIS OF 4-IMIDAZOLIN-2-ONES
Zav'yalov, S. I.,Sitkareva, I. V.,Ezhova, G. I.,Dorofeeva, O. V.,Zavozin, A. G.,Rumyantseva, E. E.
, p. 1297 - 1299 (2007/10/02)
The reaction of α-bromoketones with CO(NH2)2 and AcONH4 in aqueous acetic acid gave substituted 4-imidazolin-2-ones.
REGIODEFINED SYNTHESIS OF α-BROMO, α-PHENYLTHIO, AND α-PHENYLSELENO KETONES BY MEANS OF SPECIFIC SUBSTITUTION OF THE TRIMETHYLSILYL GROUP IN α-TRIMETHYLSILYL KETONES
Matsuda, Isamu,Sato, Susumu
, p. 47 - 52 (2007/10/02)
Regiodefined α-monobromo ketones are readily obtained by the interaction of bromine with an equivalent of α-trimethylsilyl ketones, in an excellent yield.Analogoes selective substitution of the trimethylsilyl group on phenylthio and phenylseleno groups can be attained by the reaction of phenylsulfenyl chloride or phenylselenenyl bromide with α-trimethylsilyl ketones in the presence of zinc bromide in dichloromethane.
