80608-42-0Relevant academic research and scientific papers
(Aminoethynyl)metallations, IX. Reactions of Ynamines with Cyanoketenes
Himbert, Gerhard,Henn, Lothar
, p. 218 - 225 (2007/10/02)
Ynamines 2 bearing methyl or phenyl groups at their C/C triple bond react with tert-butylcyanoketene 1a to give the cyclobutenones 3 and/or the allene carboxamides 4. 3 and 4 are the products of two different cycloaddition reactions. β-Silylated, β-germylated and β-stannylated ynamines 5 add the cyanoketenes 1 under "(aminoethynyl)metallation" to furnish the new enynamines 6.These compounds were characterized by IR and 1H NMR spectroscopy and partly by mass spectrometry.The stannyl derivatives of 6 hydrolyze very easily to the corresponding acyl ynamines 7 and react with 4-nitrobenzoyl chloride to give the 1-(aminoethynyl)vinyl benzoates 8.The diazo compound 9 is formed by the interaction of tosyl azide on the enynamine 6c, which is probably first hydrolyzed to 7a.N,N-Diethyl-N-(triphenylsilylethynyl)amine (5e) reacts with two molecules of tert-butylcyanoketene (1a) to give the allene derivative 10, probably via the corresponding enynamine 6 (R1=R2=Et, MR33=SiPh3, R4=tBu). - Keywords: Ynamines, Cyanoketenes, Cycloaddition, (Aminoethynyl)metallation, (3-Alken-1-inyl)amines
Aminoethynylations,2.-Synthesis of (Aminoethynyl)Ketones via β-Stannylated Ynamines
Himbert, Gerhard,Feustel, Michael,Jung, Marina
, p. 1907 - 1927 (2007/10/02)
The acid chlorides 1 react with (stannylethynyl)amines 2 under rather mild conditions to give the (aminoethynyl)ketones 4-7 and the chlorostannanes 8.With phthalic anhydride the interesting stannyl 2-(anilinopropioloyl)benzoates 4r' and 5r' are formed.Der
