52403-77-7Relevant academic research and scientific papers
Silylation of γ-nitro ketones as a convenient approach to the synthesis of 2-[N,N-bis(silyloxy)amino]-2,3-dihydrofurans and conjugated enoximes
Birin,Tishkov,Ioffe,Strelenko,Tartakovsky
, p. 647 - 658 (2007/10/03)
Silylation of γ-nitro ketones of the general formula R 1COCH(R2)CH(R3)CH(R4)NO2 proceeded stereoselectively to give 2-[N,N-bis(trimethylsilyloxy)amino]-2,3- dihydrofurans, conjugated enoximes, silylation products of the carbonyl group or both functional groups, or N,N-bis(trimethylsilyloxy)enamine depending on the nature and positions of the substituents in the carbon skeleton. Dihydrofuran derivatives are formed for R1 = Ar or cyclo-C 3H5. Enoximes are generated as the silylation products of the starting ketones with enhanced β-proton mobility (R3 = CO2Me or 4-NO2C6H4). The presence of an alkyl group at the carbonyl function (R1 = Alk) is favorable for the formation of enoximes. Finally, the introduction of a substituent at the α position with respect to the nitro group (R4 = Me, CO2Me, or Ph) leads to the formation of silyl enolates. Under the action of NH4F in MeOH, dihydrofurans can be transformed into substituted furans in moderate yields.
Reactions of Diphenyl(phenylethynyl)selenonium Salts with Active Methylene Compounds and Amides: First Isolation of Oxyselenuranes [10-Se-4(C3O)] as a Reaction Intermediate
Kataoka, Tadashi,Watanabe, Shin-Ichi,Yamamoto, Keiichirou,Yoshimatsu, Mitsuhiro,Tanabe, Genzoh,Muraoka, Osamu
, p. 6382 - 6386 (2007/10/03)
The reaction of the diphenyl(phenylethynyl)selenonium triflate 1a with active methylene compounds 5 and t-BuOK in THF gave furan derivatives 6. The [10-Se-4(C3O)l selenuranes 8a and 8b could be isolated from the reactions with benzoylacetonitrile 5f and with 1,3-indandione 5g, respectively, as reaction intermediates. The structures of the selenuranes 8 were elucidated by X-ray crystallography and 77Se high-resolution solid-state NMR spectroscopy. The selenuranes 8 underwent ligand coupling on standing at room temperature or refluxing in chloroform and gave the furan derivatives 6 and the ring-opened product 9. Similarly, the reaction of 1a with benzamide 13a and pivalamide 13d in the presence of NaH in THF afforded oxazole derivatives 14.
