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Allylic rearrangement: unusual products of bromination of N-acyl-2,2,4-trimethyl-1,2-dihydroquinolines and their use for N- and S-alkylation

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Abstract

Bromination of N-acyl-2,2,4-trimethyl-1,2-dihydroquinolines with N-bromosuccinimide (NBS) in CCl4 in the presence of Bz2O2 proceeded at the 4-positioned methyl group. In a DMF solution, the direction of the reaction was determined by the nature of substituent at the nitrogen atom: the reaction with one equivalent of NBS can proceed either as described above, or at position 3 with the allylic rearrangement-type migration of the multiple bond. The use of two equimoles of NBS in DMF led to 3-bromo-4-bromometh-ylene-2,2-dimethyl-3,4-dihydroquinolines. The N- and S-alkylation reactions of 3- and 4-brominated isomers resulted in the same 4-N- and 4-S-methyl derivatives.

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Authors and Affiliations

  1. Voronezh State University, 1 Universitetskaya pl., 394018, Voronezh, Russian Federation

    M. A. Potapov, A. Yu. Potapov, N. P. Novichikhina & Kh. S. Shikhaliev

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  1. M. A. Potapov
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  2. A. Yu. Potapov
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  3. N. P. Novichikhina
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  4. Kh. S. Shikhaliev
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Corresponding author

Correspondence to Kh. S. Shikhaliev.

Additional information

This work was financially supported by the Russian Science Foundation (Project No. 18-74-10097, https://rscf.ru/project/21-74-03011/).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1203–1213, May, 2023.

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Potapov, M.A., Potapov, A.Y., Novichikhina, N.P. et al. Allylic rearrangement: unusual products of bromination of N-acyl-2,2,4-trimethyl-1,2-dihydroquinolines and their use for N- and S-alkylation. Russ Chem Bull 72, 1203–1213 (2023). https://doi.org/10.1007/s11172-023-3890-2

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