1228391-75-0Relevant academic research and scientific papers
Hydrazinopeptide motifs synthesized via the Ugi reaction: An insight into the secondary structure
Krasavin, Mikhail,Bushkova, Ekaterina,Parchinsky, Vladislav,Shumsky, Alexei
, p. 933 - 942 (2010)
A number of Nα-alkyl,Nβ-acylhydrazines have been synthesized via the Ugi reaction of N-acylhydrazones with an isocyanide and trifluoroacetic acid. The trifluoroacetic acid acted as a silent partner and becomes removed upon basic workup of the reaction. These compounds have been efficiently modified further via reductive alkylation to produce Nα,Nα-dialkyl,Nβ- acylhydrazines. The two groups of novel hydrazinopeptide motifs have been shown by simple 1H NMR spectroscopic experiments to display two different secondary structure patterns. These observations were confirmed by X-ray crystallographic analysis. Combining the hydrazone and carboxylic acid moieties in one reaction precursor offers the opportunity for an intramolecular hydrazino-Ugi reaction, which was also demonstrated. Georg Thieme Verlag Stuttgart ? New York.
