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Development of a L‐Tryptophan‐Based Ligand for Regioselective Copper Catalyzed N 2 ‐Arylation of 1,2,3‐Triazoles
Author(s) -
Lopes Alexandra Basilio,
Wagner Patrick,
Kümmerle Arthur Eugen,
Bihel Frédéric,
Bourguig JeanJacques,
Schmitt Martine,
Miranda Leandro S. M.
Publication year - 2017
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201701498
Subject(s) - regioselectivity , ligand (biochemistry) , combinatorial chemistry , catalysis , tryptophan , chemistry , cycloaddition , aryl , copper , selectivity , organic chemistry , amino acid , receptor , biochemistry , alkyl
2‐aryl‐1,2,3‐triazoles are important compounds that find applications in Medicinal chemistry, diagnostics, catalysis and others. However, only few methodologies for their preparation is found in the literature. The development of a post cycloaddition N 2 selective arylation towards these compounds would benefit from a more convergent strategy. In the present communication, the development of a new tryptophan‐based ligand allowed the selective arylation of the N 2 ‐position of 1,2,3‐triazoles using recyclable CuFe 2 O 4 nanoparticles. This method was efficient in furnishing N 2 ‐arylated and heteroarylated 1,2,3‐triazoles in good yields and excellent N 2 ‐selectivity. The methodology developed found application in the synthesis of the 2‐aryl‐1,2,3‐triazoyl fragment of the drug suvorexant (Belsomra®).