Study on Synthesis of N-Protected 2-Triazolyl Azetidines


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Azetidine derivatives are interesting scaffolds in terms of medicinal chemistry. They can be regarded as structural homologs 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.



Edited by:

Valdis Kokars




V. Peipiņš et al., "Study on Synthesis of N-Protected 2-Triazolyl Azetidines", Key Engineering Materials, Vol. 762, pp. 19-24, 2018

Online since:

February 2018




* - Corresponding Author

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