Benzotriazole-assisted synthesis of α-acylaminonitriles and a conceptually novel method for peptide elongation
- 1 January 1990
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 7,p. 1853-1857
- https://doi.org/10.1039/p19900001853
Abstract
A general method for the synthesis of α-acylamino nitriles is reported. Initially, the adducts resulting from Mannich-type condensation of benzotriazole with an aldehyde and an amide are prepared. These undergo elimination of benzotriazole with cyanide to give α-arylamino nitriles in high yields. Subsequent hydrolysis of the nitrile function to the di-amides, followed by a repetition of the cyanoalkylation sequence, constitutes a novel method for the elongation of peptides.This publication has 22 references indexed in Scilit:
- The Chemistry ofN-Substituted Benzotriazoles Part 23. Synthesis of Tertiary α-Amino EstersSynthesis, 1989
- The chemistry of benzotriazole. Part 8. A novel two-step procedure for the N-alkylation of amidesJournal of the Chemical Society, Perkin Transactions 1, 1988
- Carbon-carbon bond forming reactions of ω-oxylactams in acid and neutral mediumRecueil des Travaux Chimiques des Pays-Bas, 1983
- Studies of Unusual Amino Acids and Their Peptides. VII. The Syntheses and the Reactions of IminopeptidesBulletin of the Chemical Society of Japan, 1977
- Reaction of N-(Dialkylaminomethyl) amides and N-(α-Dialkylaminobenzyl) amides with Sulfides and CyanideCHEMICAL & PHARMACEUTICAL BULLETIN, 1973
- Hydrolysis of N-AcylaminonitrilesJournal of Synthetic Organic Chemistry, Japan, 1972
- Eine neue Darstellungsweise von α‐N‐Formylaminonitrilen, α‐N‐Formylaminosäureamiden und α‐ sowie β‐Aminosäuren1)European Journal of Organic Chemistry, 1970
- A Simple Synthesis of 3,3,3‐TrifluoroalanineAngewandte Chemie International Edition in English, 1967
- Umsetzungen von N‐substituierten Amino‐iminoäthernEuropean Journal of Inorganic Chemistry, 1956
- Ueber die Oxydation mittelst WasserstoffsuperoxydEuropean Journal of Inorganic Chemistry, 1885