Synthesis of 1,2,4-Oxadiazoles Bearing Chiral N-Protected α-Amino Acids

Keywords

one-pot synthesis - 1,2,4-oxadiazoles - oxadiazole heterocycles - amidoximes

Significance

Oxadiazole-containing amino acids are privileged scaffolds in the pharmaceutical industry, enhancing the stability and bioavailability of drug candidates. In 2004, Braga and Dornelles developed a one-pot synthesis of chiral N-protected α-amino acid derived 1,2,4-oxadiazoles.

Comment

Various N-protected amino acids were reacted with amidoximes in the presence of N,N′-dicyclohexylcarbodiimide (DCC) to afford smoothly the desired 1,2,4-oxadiazoles bearing chiral N-protected α-amino acids in good yields. This one-pot, simple protocol uses inexpensive and readily available DCC as the reagent.

Publication History

Article published online:
28 January 2025