132278-98-9Relevant academic research and scientific papers
Inhibition of human alcohol dehydrogenases by formamides
Schindler, John F.,Berst, Kristine B.,Plapp, Bryce V.
, p. 1696 - 1701 (2007/10/03)
Human alcohol dehydrogenase (HsADH) comprises class I (α, β, and γ), class II (π), and class IV (σ) enzymes. Selective inhibitors of the enzymes could be used to prevent the metabolism of alcohols that form toxic products. Formamides are unreactive analog
Aggregation Studies of Lithium Dialkylamides. The Role of Aggregates in the Carbonylation Reaction
Nudelman, N. S.,Lewkowicz, E.,Furlong, J. J. P.
, p. 1847 - 1852 (2007/10/02)
13C NMR spectroscopy and isotopic exchange in carbonylation intermediates have been successfully employed to characterize aggregation of lithium dialkylamides in THF solution.It is shown that lithium (3-oxapentamethylene)amide forms a 1 : 1 mixed aggregate with morpholine.The aggregate remains even in diluted THF solution.Lithium pentamethyleneamide also forms aggregates with piperidine while the less acidic amines do not form mixed aggregates with the corresponding lithium dialkylamide either in the solid state or in THF solution.The product composition in the carbonylation reaction of lithium dialkylamides is highly dependent on their aggregation states, and this phenomenon can be successfully used for synthetic purposes.
Carbon-Carbon Bond Formation through the Carbonylation of Lithium Dialkylamides. One Pot Synthesis of N-Alkyl-Substituted Formamides, Glyoxylamides, and Hydroxymalonamides
Perez, Daniel G.,Nudelman, N. Sbarbati
, p. 408 - 413 (2007/10/02)
The reaction of lithium dialkylamides 1 (dialkyl = dibutyl, dipentyl, dicyclohexyl, 3-oxapentamethylene, and isopropyl cyclohexyl) with carbon monoxide was examined under several reaction conditions.It is shown that the corresponding lithium carbamoyl is the first intermediate and its further reactions can lead to dialkylformamides 2, dialkylglyoxylamides 3, or tetraalkylhydroxymalonamides 4.Dialkylamides were previously assumed to come from hydrolysis of lithium carbamoyls, and these represent an unexplained "island of stability" among the area of acyl anions.Evidence is given that casts doubts on this assumption and suggests that 2 comes from the cleavage of lithium tetraalkylurea dianion.The yields of 2, 3, or 4 obtained by this one-step, rapid procedure are much higher than those afforded by the usual several steps methods of preparation, especially for compounds 3 and 4.Tetraalkylureas, tetraalkyloxalamines, or tetraalkylketomalonamides can be obtained in good yield by the same general procedure, followed by treatment ot the reaction mixture with oxygen after the carbon monoxide absorption has ceased and before the regular workup.
