85241-00-5Relevant articles and documents
Selective syntheses of metalated pyridines from two different unsymmetrical acetylenes, a nitrile, and a titanium(II) alkoxide
Suzuki, Daisuke,Tanaka, Ryoichi,Urabe, Hirokazu,Sato, Fumie
, p. 3518 - 3519 (2002)
Cyclotrimerization of two different, unsymmetrical acetylenes and p-toluenesulfonylnitrile with a divalent titanium alkoxide reagent, Ti(O-i-Pr)4/2 i-PrMgCl, yielded single pyridyltitanium compounds in a highly selective manner. These metalated pyridines were confirmed by deuteriolysis to give the corresponding deuterated pyridines and underwent iodinolysis and copper-catalyzed alkylation to demonstrate their synthetic utility. Alternatively, a different type of cyclotrimerization of an alkynamide, terminal acetylenes, and α-alkoxynitriles mediated by the same titanium(II) alkoxide again proceeded in a highly selective manner to give single pyridines having a titanated side chain. Copyright
Z-Selective phosphine promoted 1,4-reduction of ynoates and propynoic amides in the presence of water
Drikermann, Denis,Kupfer, Stephan,Seifert, Fabian,Steinmetzer, Johannes,Vilotijevic, Ivan,Zi, You
supporting information, p. 6092 - 6097 (2021/07/21)
Phosphine-mediated reductions of substituted propynoic esters and amides in the presence of water yield the partially reduced α,β-unsaturated esters and amides with highZ-selectivity. The competitivein situ ZtoE-isomerization of the product in some cases lowers theZtoEratios of the isolated α,β-unsaturated carbonyl products. Reaction time and the amounts of phosphine and water in the reaction mixture are the key experimental factors which control the selectivity by preventing or reducing the rates ofZ- toE-product isomerization. Close reaction monitoring enables isolation of theZ-alkenes with high selectivities. The computational results suggest that the reactions could be highlyZ-selective owing to the stereoselective formation of theE-P-hydroxyphosphorane intermediate.
Method for synthesizing alpha, beta-unsaturated alkyne amide compound through oxidative carbonylation
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Paragraph 0027; 0028, (2021/01/11)
The invention relates to a method for synthesizing an alpha, beta-unsaturated alkyne amide compound by oxidative carbonylation, which comprises the following steps: by using terminal alkyne and a diamine compound as raw materials, water-soluble alpha-diim
N-triflyl-propiolamides: Preparation and transamidation reactions
Fiore, Vito A.,Maas, Gerhard
, p. 3586 - 3595 (2019/05/27)
N-Trifluoromethylsulfonyl-propiolamides have been prepared by two methods: a) N-triflation of secondary acetylenic carboxanilides, prepared in two steps from terminal alkynes, with triflic anhydride (Tf2O) and b) from terminal alkynes and an aryl or alkyl isocyanate followed by Tf2O in a consecutive one-pot reaction. The title compounds are bench-stable and insensitive to water and alcohols but amenable to transamidation reactions with a wide range of amine nucleophiles. Conversely, they are excellent reagents for the propynoylation of ammonia, primary and secondary amines, anilines, and hydrazines.
