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Copper‐Free Solid‐Phase Synthesis of Triazolo[1,5‐ a ][1,4]diazepin‐6‐ones
Author(s) -
Kriegelsteinová Patricia,
Lemrová Barbora,
Ručilová Veronika,
Soural Miroslav
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001403
Subject(s) - chemistry , solid phase synthesis , peptidomimetic , alkylation , moiety , propargyl , combinatorial chemistry , acylation , mitsunobu reaction , organic chemistry , catalysis , peptide , biochemistry
Synthesis of triazolo[1,5‐ a ][1,4]diazepin‐6‐ones on solid support is reported in this article. Amino acids immobilized on Wang resin were nosylated and alkylated with propargyl alcohol, but‐2‐yn‐1‐ol or different 3‐phenylprop‐2‐yn‐1‐ols using Mitsunobu alkylation conditions. After denosylation, acylation with Fmoc‐azidoalanine yielded linear precursors that were thermally cyclized on resin to give immobilized triazolodiazepinones. After cleavage from the polymer support, the target compounds were obtained in high crude purities and good overall yields. Furthermore, the synthetic approach was applied to convenient solid‐phase synthesis of oligopeptide containing the triazolodiazepinone moiety as the peptidomimetic heterocyclic constraint.