Abstract:Substitution reactions O 0040C-Aminoimidoylation and C-Thiocarbamoylation of Esters, Sulfones, and Ketones. -The reactions allow new and easy access to functionalized amidines and thioamides. Some amidines exist in form of their enamine tautomers. Interestingly, coupling of the N-benzylated thiourea derivative (VI) with ketones does not yield the corresponding thioamides but oxazolinethiones like (VII) or (IX). -(KATRITZKY*, A. R.; KHASHAB, N. M.; HAASE, D. N.; YOSHIOKA, M.; GHIVIRIGA, I.; STEEL, P.
“…N ‐Fmoc‐protected( α ‐aminoacyl)benzotriazoles 2a–g were prepared in 72–90% yield from the reaction of N α ‐Fmoc‐protected amino acids 1a–g (purchased from Peptides International, Louisville, KY, USA and used without further purification) with 4 equivalents of 1 H ‐benzotriazole and 1 equivalent of SOCl 2 in THF at 20 °C for 2 h following our published procedure (the reaction time for the complete conversion of Fmoc‐ L ‐Ala‐OH to Fmoc‐ L ‐Ala‐Bt 2a was 18 h in the presence of 2.5 equivalents of SOCl 2 ) (Scheme 1, Table 1) (5,9,19). The original chirality was preserved in all cases (>95% as evidenced by NMR), and the benzotriazole derivatives 2a–g are moisture insensitive and easy to handle.…”
A novel microwave-assisted solid-phase peptide synthesis utilizing N-Fmoc-protected(alpha-aminoacyl)benzotriazoles was applied in the preparation of tri-, tetra-, penta-, hexa-, and heptapeptides in 71% average crude yield.
“…N ‐Fmoc‐protected( α ‐aminoacyl)benzotriazoles 2a–g were prepared in 72–90% yield from the reaction of N α ‐Fmoc‐protected amino acids 1a–g (purchased from Peptides International, Louisville, KY, USA and used without further purification) with 4 equivalents of 1 H ‐benzotriazole and 1 equivalent of SOCl 2 in THF at 20 °C for 2 h following our published procedure (the reaction time for the complete conversion of Fmoc‐ L ‐Ala‐OH to Fmoc‐ L ‐Ala‐Bt 2a was 18 h in the presence of 2.5 equivalents of SOCl 2 ) (Scheme 1, Table 1) (5,9,19). The original chirality was preserved in all cases (>95% as evidenced by NMR), and the benzotriazole derivatives 2a–g are moisture insensitive and easy to handle.…”
A novel microwave-assisted solid-phase peptide synthesis utilizing N-Fmoc-protected(alpha-aminoacyl)benzotriazoles was applied in the preparation of tri-, tetra-, penta-, hexa-, and heptapeptides in 71% average crude yield.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.