biostudies-literatureGudelis EKaunas University of TechnologyVipergen ApS (Copenhagen, Denmark) and the Doctoral Fund of Kaunas University of Technology1091https://www.ebi.ac.uk/biostudies/studies/S-EPMC9921373biostudies-literatureUnknown28(3)In this paper, a simple and efficient synthetic route for the preparation of new heterocyclic amino acid derivatives containing azetidine and oxetane rings was described. The starting (<i>N</i>-Boc-azetidin-3-ylidene)acetate was obtained from (<i>N</i>-Boc)azetidin-3-one by the DBU-catalysed Horner-Wadsworth-Emmons reaction, followed by aza-Michael addition with NH-heterocycles to yield the target functionalised 3-substituted 3-(acetoxymethyl)azetidines. Methyl 2-(oxetan-3-ylidene)acetate was obtained in a similar manner, which was further treated with various (<i>N</i>-Boc-cycloaminyl)amines to yield the target 3-substituted 3-(acetoxymethyl)oxetane compounds. The synthesis and diversification of novel heterocyclic amino acid derivatives were achieved through the Suzuki-Miyaura cross-coupMolecules (Basel, Switzerland)Synthesis of New Azetidine and Oxetane Amino Acid Derivatives through Aza-Michael Addition of NH-Heterocycles with Methyl 2-(Azetidin- or Oxetan-3-Ylidene)Acetates.PMC9921373Doctoral Fund of Kaunas University of Technology No. A-410, approved 26 June 2019A-410Jankauskas RStanciauskaite MKleiziene NKrikstolaityte SMilisiunaite VSlok FAGudelis EBieliauskas ASachleviciute USackus AfalseSynthesis of New Azetidine and Oxetane Amino Acid Derivatives through Aza-Michael Addition of NH-Heterocycles with Methyl 2-(Azetidin- or Oxetan-3-Ylidene)Acetates.In this paper, a simple and efficient synthetic route for the preparation of new heterocyclic amino acid derivatives containing azetidine and oxetane rings was described. The starting (<i>N</i>-Boc-azetidin-3-ylidene)acetate was obtained from (<i>N</i>-Boc)azetidin-3-one by the DBU-catalysed Horner-Wadsworth-Emmons reaction, followed by aza-Michael addition with NH-heterocycles to yield the target functionalised 3-substituted 3-(acetoxymethyl)azetidines. Methyl 2-(oxetan-3-ylidene)acetate was obtained in a similar manner, which was further treated with various (<i>N</i>-Boc-cycloaminyl)amines to yield the target 3-substituted 3-(acetoxymethyl)oxetane compounds. The synthesis and diversification of novel heterocyclic amino acid derivatives were achieved through the Suzuki-Miyaura cross-coup2023-01-01T00:00:00Z2023 Jan2025-08-16T03:06:23.543Z2024-10-18T03:13:43.627ZS-EPMC99213733677076210.3390/molecules28031091