Braga AL *,
Lüdtke DS,
Alberto EE,
Dornelles L *,
Filho WAS,
Corbellini VA,
Rosa DM,
Schwab RS.
Universidade Federal de Santa Maria and Universidade de Santa Cruz do Sul,
Brazil
‘One-Pot’ Synthesis of Chiral N-Protected α-Amino Acid-Derived
1,2,4-Oxadiazoles.
Synthesis 2004; 1589-1594
DOI:
10.1055/s-2004-822391
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.
