A Metal-Free Cycloaddition of α-Diazoacetates with Amino Acid-Derived NHPI Esters for the Facile Synthesis of 1,2,4-Triazoles.
Org Lett
; 26(26): 5511-5516, 2024 Jul 05.
Article
in En
| MEDLINE
| ID: mdl-38904436
ABSTRACT
1,2,4-Triazoles are privileged scaffolds for many pharmaceuticals, and methods for structurally diverse compound libraries are of current interest. Here we report an efficient coupling of α-diazoacetates with amino acid-derived alkyl N-hydroxy phthalimide esters, under metal-free conditions involving 1,8-diazabicyclo(5.4.0)undec-7-ene as the base, with which highly functionalized 1,2,4-triazoles can be obtained in excellent yields with remarkable functional group tolerance. Preliminary studies revealed that 1,2,4-triazole 3a exhibits potent inhibition of tyrosinase activities in melanoma B16F10 cell lines, demonstrating promising skin-whitening properties.
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Triazoles
/
Esters
/
Amino Acids
Limits:
Animals
Language:
En
Journal:
Org Lett
Journal subject:
BIOQUIMICA
Year:
2024
Document type:
Article
Affiliation country:
China