A series of methyl 2-amino-1,3-selenazole-5-carboxylates possessing a chiral pyrrolidin-2-yl, piperidin-2-yl, or piperidin-3-yl substituent at the C-4 atom of the heteroaromatic ring was designed and synthesized. In the first stage of the synthesis, the carboxylic acid functional group of the L-proline or related chiral heterocyclic amino acid was converted to the corresponding β-keto ester, which was then α-brominated with N-bromosuccinimide. The subsequent reaction of the α-brominated β-keto ester with selenourea afforded the target methyl 2-amino-1,3-selenazole-5-carboxylate. The structures of the novel heterocyclic compounds were confirmed by 1H, 13C, and 77Se NMR spectroscopy and HRMS.
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This work has been accomplished with financial support provided by Vipergen ApS company (Copenhagen, Denmark).
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(4), 469–473
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Malinauskienė, V., Kveselytė, A., Dzedulionytė, K. et al. L-Proline and related chiral heterocyclic amino acids as scaffolds for the synthesis of functionalized 2-amino-1,3-selenazole-5-carboxylates. Chem Heterocycl Comp 54, 469–473 (2018). https://doi.org/10.1007/s10593-018-2291-1
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DOI: https://doi.org/10.1007/s10593-018-2291-1