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TaCl5 in the synthesis of amides from saturated monobasic carboxylic acids and functionally substituted primary aromatic amines

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Abstract

The reactions of saturated monobasic carboxylic acids with functionally substituted primary aromatic amines (3-amino-2-naphthol, benzo[d]thiazol-2-amine, and 4,4′-oxydianiline) with TaCl5 (0.2 equiv.) were found to be accompanied by the selective formation of carboxylic acid amides of various structures. A mechanism for the amidation of carboxylic acids in the presence of TaCl5 was proposed.

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Funding

This work was financially supported by the Russian Science Foundation (Project No. 23-23-00499). The structural studies were carried out at the Center for Collective Use of the N. D. Zelinsky Institute of the Russian Academy of Sciences and Regional Center for Collective Use “Agidel” of the Institute of Petrochemistry and Catalysis (Ufa Federal Research Center of the Russian Academy of Sciences).

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Authors and Affiliations

  1. Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of the Russian Academy of Sciences, 141 prosp. Oktyabrya, 450075, Ufa, Russian Federation

    A. M. Gabdullin, R. N. Kadikova, A. B. Yulbarisov, O. S. Mozgovoi & I. R. Ramazanov

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  1. A. M. Gabdullin
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  2. R. N. Kadikova
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  3. A. B. Yulbarisov
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  4. O. S. Mozgovoi
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Correspondence to R. N. Kadikova.

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Dedicated to the memory of Academician of the Russian Academy of Sciences G. A. Tolstikov (1933–2013).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 10, pp. 2350–2356, October, 2023.

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Gabdullin, A.M., Kadikova, R.N., Yulbarisov, A.B. et al. TaCl5 in the synthesis of amides from saturated monobasic carboxylic acids and functionally substituted primary aromatic amines. Russ Chem Bull 72, 2350–2356 (2023). https://doi.org/10.1007/s11172-023-4032-6

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  • DOI: https://doi.org/10.1007/s11172-023-4032-6

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