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Synthesis of enantiopure 3,4-dihydro-2H-1,4-benzoxazine analogues for potential biological applications

Abstract : This work describes the syntheis and conformational analysis of enantiopure 1,4-benzoxazine-based pseudodipeptides and pseudotripeptides. Enantiomers of ethyl 2,3-dibromopropionate and ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate are obtained by two strategies (i) via enantioselective synthesis and (ii) via preparative HPLC enantioseparation of racemate on multigram scale. Because of the racemization process during the enantioselective synthesis, preparative HPLC enantioseparation on racemates are successfully applied to afford enantiomers with high enantiomeric purities (ee ≥ 99.5%). Both enantiomers of the 1,4-benzoxazine compound are used to design new 1,4-benzoxazine-based pseudopeptides via peptide coupling reactions on C- and N-terminal extremities. Their conformational behaviour in solution and solid states are investigated by spectroscopic (IR, NMR) and X-Ray diffraction analyses. The results indicate (i) a predominant C5 pseudocycle involving a lone pair of electrons of oxygen in 1,4-benzoxazine ring with NH group from C-extremity elongation and (ii) a slight influence of the absolute configuration at C2 position of 1,4-benzoxazine scaffold and the side chains of amino acids.
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Submitted on : Monday, March 22, 2021 - 2:59:03 PM
Last modification on : Sunday, June 26, 2022 - 3:06:33 AM
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  • HAL Id : tel-03176568, version 1


Hong-Ngoc Pham. Synthesis of enantiopure 3,4-dihydro-2H-1,4-benzoxazine analogues for potential biological applications. Chemical and Process Engineering. Université de Lorraine, 2020. English. ⟨NNT : 2020LORR0186⟩. ⟨tel-03176568⟩



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