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Bismuth-catalyzed arylation of ethyl glyoxylate with aniline via N–H insertion

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Abstract

Glycine derivatives such as ethyl 2-(4-aminophenyl)-2-(phenylamino) acetate is an exciting and essential non-proteinogenic class of amino acids. Herein, we report an efficient and novel route to synthesize glycine derivatives using ethyl glyoxylate, aniline, and its derivatives catalyzed by bismuth salts. In our scheme, mild, non-toxic, and commercially viable reagents were utilized. The synthesized moieties were characterized by ESI-MASS, 1H-NMR, 13C-NMR, and XRD techniques. The target glycine derivatives were successfully obtained with a maximum yield of 87%. Moreover, the reaction is very green as water is the only byproduct.

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Acknowledgements

This work was supported by the Science and Engineering Research Board, Government of India (File No. EEQ/2018/000428). The authors thank CIF, Pondicherry University, for the NMR spectroscopic facility and DST-FIST for the ESI-MS facility and Single crystal XRD facility. Mohd. Aamir Bin Riyaz and Premkumar G acknowledge Pondicherry University for providing University Research Fellowship.

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  1. Department of Chemistry, Pondicherry University, R.V. Nagar, Kalapet, Puducherry, 605014, India

    Mohd. Aamir Bin Riyaz, G. Premkumar & Toka Swu

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  1. Mohd. Aamir Bin Riyaz
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  3. Toka Swu
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Correspondence to Toka Swu.

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Riyaz, M.A.B., Premkumar, G. & Swu, T. Bismuth-catalyzed arylation of ethyl glyoxylate with aniline via N–H insertion. Mol Divers 27, 167–175 (2023). https://doi.org/10.1007/s11030-022-10411-x

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  • DOI: https://doi.org/10.1007/s11030-022-10411-x

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