89566-52-9Relevant academic research and scientific papers
One-pot synthesis of 3-(trimethylsilyl)propynamides
Medvedeva,Andreev,Safronova
experimental part, p. 1466 - 1470 (2011/02/24)
A highly efficient one-pot procedure was developed for the synthesis of 3-trimethylsilylpropynamides by acylation of amines with trimethylsilylpropynoyl chloride generated in situ. Selective N-acylation and N,O-bis-acylation of -amino alcohols with format
Convergent and rapid assembly of substituted 2-pyridones through formation of N-alkenyl alkynylamides followed by gold-catalyzed cycloisomerization
Imase, Hidetomo,Noguchi, Keiichi,Hirano, Masao,Tanaka, Ken
supporting information; experimental part, p. 3563 - 3566 (2009/05/07)
(Chemical Equation Presented) A new method for the convergent and rapid assembly of substituted 2-pyridones was developed through the formation of N-alkenyl alkynylamides (amide-linked 1,5-enynes) by N-acylation of !mines with alkynoyl chlorides and the subsequent cationic Au(l)/PPh3-catalyzed cycloisomerization.
Synthesis and mass-spectrometric investigation of N-Aryl-3-trimethylsilyl-2-propyn-1-carboxamides
Safronova,Medvedeva,Klyba,Bochkarev,Andreev
, p. 184 - 190 (2007/10/03)
Reaction of a number or arylamines with trimethylsilylpropiolyl chloride afforded unknown α,β-siliconacetylenic N-arylamides. IR, 1H, 13C, and 29Si NMR spectra and mass spectra thereof were studied. The primary act of arylamides decay is the rupture of the amide bond and localization of the charge on the acyl fragment. A large contribution into the spectrum of 3-trimethylsilyl-2-propynamide make the peaks of rearranged ions.
Acetylenic Amides. 2. The Generation and Reactions of Dianions Derived From 2-Propynamides
Coppola, Gary M.,Damon, Robert E.
, p. 1133 - 1140 (2007/10/02)
The dianion of N-benzyl-2-propynamide can be generated by the treatment of 4 with two equivalents of LDA at -65 deg C or ethylmagnesium bromide at -20 deg C.The trilithio species 6 is readily formed using 3 equivalents of LDA.Reaction of 5 with aldehydes or ketones produce hydroxypropynamides 9 in good yields.Silation of 5a with chlorotrimethylsilane produces N-benzyl-3-trimethylsilyl-2-propynamide (13) in high yield.Reduction of 9 furnishes either fully saturated amides 15 or partially reduced cis-olefins 16 or 18.Compounds 16, on heating, rearrange to 4-ketoamides 17.Carboxylation of 5a with carbon dioxide produces 3-benzyl-2,4-dioxo-5-oxazidinylacetic acid (11).Warming 11 in dimethyl sulfoxide results in the loss of carbon dioxide and the formation of N-benzylpyruvamide (21).
