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Reactions of N- and C-alkenylanilines: VI. Synthesis of 6-methyl-2-[(E or Z)-1-propenyl]anilines and the corresponding anilides and their reaction with bromine

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Abstract

Isomerization of 2-allyl-6-methylaniline by the action of potassium hydroxide at 300°C afforded cis and trans isomers of 2-methyl-6-(1-propenyl)aniline which were converted into the corresponding carbamates by treatment with ethyl chloroformate. Ethyl 2-methyl-6-(1-propenyl)phenylcarbamates reacted with bromine to give mixtures of 4-(1-bromoethyl)-8-methyl-1,4-dihydro-2H-3,1-benzoxazin-2-one and ethyl 2- methyl-6-(1,2-dibromopropyl)phenylcarbamates. Treatment of the same compounds with N-bromosuccinimide resulted in formation of 2-ethoxy-4H-3,1-benzoxazine derivatives. The reaction of N-{6-methyl-2-[(Z)- 1-propenyl]-phenyl}methanesulfonamide gave a mixture of stereoisomeric N-[6-methyl-2- (1,2-dibromopropyl)-phenyl]-methanesulfonamides.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Research Center, Russian Academy of Sciences, pr. Oktyabrya 71, Ufa, 450054, Bashkortostan, Russia

    I. S. Afon’kin, A. M. Sotnikov, R. R. Gataullin, L. V. Spirikhin & I. B. Abdrakhmanov

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  1. I. S. Afon’kin
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  2. A. M. Sotnikov
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  3. R. R. Gataullin
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  4. L. V. Spirikhin
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  5. I. B. Abdrakhmanov
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__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 12, 2004, pp. 1815–1818.

Original Russian Text Copyright © 2004 by Afon’kin, Sotnikov, Gataullin, Spirikhin, Abdrakhmanov.

For communication V, see [1].

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Afon’kin, I.S., Sotnikov, A.M., Gataullin, R.R. et al. Reactions of N- and C-alkenylanilines: VI. Synthesis of 6-methyl-2-[(E or Z)-1-propenyl]anilines and the corresponding anilides and their reaction with bromine. Russ J Org Chem 40, 1764–1768 (2004). https://doi.org/10.1007/s11178-005-0096-z

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  • DOI: https://doi.org/10.1007/s11178-005-0096-z

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