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

Bromination of N -acyl-2,2,4-trimethyl-1,2-dihydroquinolines with N -bromosuccinimide (NBS) in CCl 4 in the presence of Bz 2 O 2 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...

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Bibliographic Details
Published in:Russian chemical bulletin 2023-05, Vol.72 (5), p.1203-1213
Main Authors: Potapov, M. A., Potapov, A. Yu, Novichikhina, N. P., Shikhaliev, Kh. S.
Format: Article
Language:English
Subjects:
Alkylation
Bromination
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Inorganic Chemistry
Nitrogen
Organic Chemistry
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Summary:Bromination of N -acyl-2,2,4-trimethyl-1,2-dihydroquinolines with N -bromosuccinimide (NBS) in CCl 4 in the presence of Bz 2 O 2 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.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-023-3890-2