Chemoselective reactions of trimethylsilylpropynal with aminopyrimidines and amino acid esters
摘要:
Highly efficient chemoselective 1,2-addition of 2-aminopyrimidines and D,L-amino acid esters to substituted propynals was performed. Acid-catalyzed addition of 2-aminopyrimidine and 2-amino-4-methylpyrimidine to trimethylsilyl- and phenylpropynals gave previously unknown acetylenic aminals. Reactions of alpha-amino acid methyl esters (alanine and lysine) with trimethylsilylpropynal led to the formation of new aza enynes in high yield. Regardless of the reactant ratio, trimethylsilylpropynal reacted with lysine at both amino groups with formation of bis-aza enyne.
2-(Fluoromethyl or chloromethyl)-2,5-diaminopentanoic acid, 2-(fluoromethyl or chloromethyl)-2,6-diaminohexanoic acid, and 2-fluoromethyl-2-amino-5-guanidinopentanoic acid, and certain derivatives thereof, are inhibitors of ornithine decarboxylase. Methods of preparing the compounds and derivatives are also described.