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Facile synthesis of novel amino acid-like building blocks by N-alkylation of heterocyclic carboxylates with N-Boc-3-iodoazetidine

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Abstract

An efficient protocol providing easy access to highly functionalized heterocyclic compounds as novel organic building blocks was developed by coupling alkyl pyrazole-, indazole- and indolecarboxylates with N-Boc-3-iodoazetidine. The synthesized compounds are representatives of constrained non-chiral synthetic azole carboxylates in their N-Boc protected ester forms. Diversification of the prepared heterocyclic building blocks was achieved via application of palladium-catalyzed Suzuki–Miyaura cross-coupling reactions. In total, 34 building blocks were obtained to form a highly diversified small molecule collection. The structure of the novel heterocyclic compounds was investigated and verified by advanced NMR spectroscopy methods.

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Acknowledgements

This work has been accomplished with financial support provided by Vipergen ApS company (Copenhagen, Denmark).

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Authors and Affiliations

  1. Department of Organic Chemistry, Kaunas University of Technology, Radvilėnų pl. 19, 50254, Kaunas, Lithuania

    Monika Iškauskienė & Algirdas Šačkus

  2. Institute of Synthetic Chemistry, Kaunas University of Technology, K. Baršausko g. 59, 51423, Kaunas, Lithuania

    Monika Iškauskienė, Greta Ragaitė & Algirdas Šačkus

  3. Vipergen ApS, Gammel Kongevej 23A, 1610, Copenhagen V, Denmark

    Frank A. Sløk

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  1. Monika Iškauskienė
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Correspondence to Monika Iškauskienė.

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Iškauskienė, M., Ragaitė, G., Sløk, F.A. et al. Facile synthesis of novel amino acid-like building blocks by N-alkylation of heterocyclic carboxylates with N-Boc-3-iodoazetidine. Mol Divers 24, 1235–1251 (2020). https://doi.org/10.1007/s11030-019-09987-8

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