Study on Synthesis of N-Protected 2-Triazolyl Azetidines
Key Engineering Materials 2018
Vilnis Peipiņš, Krista Gulbe, Māris Turks

Azetidine derivatives are interesting scaffolds in terms of medicinal chemistry. They can be regarded as structural homologues of aziridines. Herein we report synthetic approach to the novel N-protected 2-triazolyl azetidines which are structurally similar to our previously described aziridine derivatives with matrix metalloproteinase-2 inhihbitory activities. The synthetic rout includes ring closing of ethyl 2,4-dibromobutanoate, selective reduction of ester to aldehyde and transformation of the latter to terminal alkyne by Ohira-Bestmann reagent. 2-Ethynyl azetidines as key intermediates were transformed into triazole derivatives by Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction.


Keywords
2-triazolyl azetidine, benzyl protected azetidine, 2-ethynyl azetidine
DOI
10.4028/www.scientific.net/KEM.762.19

Peipiņš, V., Gulbe, K., Turks, M. Study on Synthesis of N-Protected 2-Triazolyl Azetidines. In: Key Engineering Materials, Latvia, Riga, 20-20 October, 2017. Switzerland: Trans Tech Publications, 2018, pp.19-24. ISSN 1013-9826. e-ISSN 1662-9795. Available from: doi:10.4028/www.scientific.net/KEM.762.19

Publication language
English (en)
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