53856-98-7Relevant academic research and scientific papers
An acetal acylation methodology for producing diversity of trihalomethyl-1,3-dielectrophiles and 1,2-azole derivatives
Bare?o, Valéria D.O.,Santos, Daiane S.,Frigo, Leandro M.,de Mello, Debora L.,Malavolta, Juliana L.,Blanco, Rogerio F.,Pizzuti, Lucas,Flores, Darlene C.,Flores, Alex F.C.
, p. 244 - 264 (2020/01/03)
A series of functionalized 1,1,1-trihalo-4-methoxy-3-alken-2-ones [CX3C(O)CR1=CROMe, where X = F or Cl; R = n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-tridecyl, (CH2)2CH=C(Me)2, (CH2)2Ph, (CH2)2-(4-HOC6H4), (CH2)2-(4-MeOC6H4), (CH2)2CO2Me, (CH2)3CO2Me, CH(SMe)CH3, CH2(2-MeOC6H4), and R1 = H, and R = H and R1 = n-decyl] were synthesized from respective alkyl methyl ketones or aldehyde via acetal acylation using trifluoroacetic anhydride and trichloroacetyl chloride. 1,1,1-Trihalo-4-methoxy-3-alken-2-ones with acid-compatible substituents were easily hydrolyzed to respective trihalomethyl-1,3-diketones. The 1,1,1-trihalo-4-methoxy-3-alken-2-ones and/or respective trihalomethyl-1,3-diketones were reacted regiospecifically with hydroxylamine hydrochloride, leading to isoxazole derivatives, and with hydrazines, leading to respective 1H-pyrazole derivatives. The structures of all compounds were assigned based on nuclear magnetic resonance (NMR) and mass spectrometric data. This method represents an efficient pathway for the regioselective trihaloacetylation of asymmetrically substituted alkyl methyl ketones and highly self-condensing aldehydes. Moreover, this approach allows the introduction of biologically recognizable moieties, such as those from levulinic acid, sulcatone (prenyl), benzylacetone, anisylacetone, and raspberry ketone, as synthetic molecular targets.
Silver-Catalyzed Olefination of Acetals and Ketals with Diazoesters to β-Alkoxyacrylates
Li, Jiawen,Qian, Bo,Huang, Hanmin
supporting information, p. 7090 - 7094 (2018/11/23)
The first silver-catalyzed reaction of acetals or ketals with diazoesters leading to trisubstituted or tetrasubstituted β-alkoxyacrylates is now reported. A broad range of acetals and ketals bearing different substituents is compatible with this protocol and thus provides an attractive approach for the synthesis of complex β-alkoxyacrylates. The power of this method was further demonstrated by the successful synthesis of picoxystrobin, which is one of the most popular agricultural fungicides commercialized by Dupont.
Highly efficient acetalization of carbonyl compounds catalyzed by anilin-aldehyde resin salts
Tanemura, Kiyoshi,Suzuki, Tsuneo
supporting information, p. 797 - 799 (2015/06/22)
A mild procedures for the syntheses of ethylene acetals and dimethyl acetals from the corresponding aldehydes and ketones catalyzed by 1mol% of anilinealdehyde resin salts are described. This method is also useful for the synthesis of dimethyl acetals of diaryl ketones.
Mesoporous aluminosilicate-catalyzed allylation of carbonyl compounds and acetals
Ito, Suguru,Hayashi, Akira,Komai, Hirotomo,Yamaguchi, Hitoshi,Kubota, Yoshihiro,Asami, Masatoshi
supporting information; experimental part, p. 2081 - 2089 (2011/04/19)
A mesoporous aluminosilicate (Al-MCM-41) was found to be an effective heterogeneous catalyst for the reaction of both carbonyl compounds and acetals with allylsilanes to afford the corresponding homoallyl silyl ethers and homoallyl alkyl ethers, respectively. Both the mesoporous structure and the presence of aluminum moiety were indispensable for the high catalytic activity of Al-MCM-41. Moreover, Al-MCM-41 could catalyze the reaction of acetals chemoselectively in the presence of the corresponding carbonyl compounds. The solid acid catalyst Al-MCM-41 could be recovered easily by filtration and could be reused three times without a significant loss of catalytic activity.
Reductive coupling of aromatic dialkyl acetals using the combination of zinc and chlorotrimethylsilane in the presence of potassium carbonate
Hatano, Bunpei,Nagahashi, Keita,Habaue, Shigeki
, p. 1418 - 1419 (2008/03/14)
The treatment of aromatic acetals with zinc and chlorosilane in the presence of potassium carbonate in toluene brought about facile and effective reductive coupling to give the corresponding coupling products. Copyright
Single-pass reaction column system with super br?nsted acid-loaded resin
Ishihara, Kazuaki,Hasegawa, Aiko,Yamamoto, Hisashi
, p. 1296 - 1298 (2007/10/03)
Various acid-promoted reactions gave the desired products in high yields by passing a solution of reactants through a reaction column packed with polystyrene-bound super Br?nsted acid (1) just once. Polar and nonpolar organic solvent-swellable 1 is much superior to Nafion SAC-13 (2) as a Br?nsted acid-loaded resin packed in the column.
Polystyrene-bound tetrafluorophenylbis(trifiyl)methane as an organic-solvent-swellable and strong Bronsted acid catalyst
Ishihara, Kazuaki,Hasegawa, Aiko,Yamamoto, Hisashi
, p. 4077 - 4079 (2007/10/03)
Several advantages over inorganic solid acids such as zeolites and perfluororesinsulfonic acids such as Nafion are offered by the new reusable polystyrene-bound catalyst 1: a broader range of applications, improved yields, improved selectivity, and milder reaction conditions. Tf = F3CSO2.
NEW ALKENYLCOBALT(III) COMPLEXES FROM OXIDATIVE DENITROGENATION OF HYDRAZONES BY COBALT SCHIFF BASE COMPLEX-DIOXYGEN COMPLEX
Nishinaga, Akira,Yamazaki, Shigekazu,Matsuura, Teruo
, p. 6309 - 6312 (2007/10/02)
Oxidation of hydrazones of aliphatic ketones by a Co(salen)-dioxygen system in dichloromethane results in oxidative denitrogenation of the hydrazones to give new 1-alkenylcobalt(III) complexes.Treatment of the alkenyl complexes with sodium borohydride gives the corresponding cis-olefins.
