Synthesis of chiral α-amino acid-derived 1H-1,2,4-triazoles and 1,2,4-triazines?

MedChemComm Pub Date: 2011-11-14 DOI: 10.1039/C1MD00177A

Abstract

Enantiopure N-(Cbz, Fmoc, Boc, or Ac)-1H-1,2,4-triazole- (8a–p, and 8f′) and previously unknown N-Cbz-1,2,4-triazine-derived α-amino acids (11a–d, 11d′, 13a,b, and 13a′) were synthesized using microwave irradiation. Reaction conditions led unexpectedly to simultaneous cyclization, deprotection and acetylation of N-Boc-aminoacylamidrazones 7m,n to afford N-acetyl-1H-1,2,4-triazoles 8o,p.

Graphical abstract: Synthesis of chiral α-amino acid-derived 1H-1,2,4-triazoles and 1,2,4-triazines
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