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Functiaonalization of 2-(1-Cyclohexen-1-yl)aniline Derivatives

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Abstract

The reaction of 2-(1-cyclohexen-1-yl)aniline and -6-methylaniline with phthalic anhydride has afforded 2-(2-cyclohex-1-en-1-ylphenyl)- and 2-(2-cyclohex-1-en-1-ylphenyl)-6-methylphenyl)-1H-isoindole-1,3(2H)-diones. The reaction of the obtained isoindole-1,3-diones with bromine in dichloromethane in the presence of sodium bicarbonate has led to the formation of the product of pseudo-allylic halogenation. Replacement of the halogen atom by methoxy group has been performed by keeping 2-[2-(6-bromocyclohex-1-en-1-ylphenyl)-6-methylphenyl)]-1H-isoindole-1,3(2H)-dione in a methanolic solution in the presence of NaHCO3. The reaction of 2-(2-cyclohex-1-en-1-yl-6-methylphenyl)-1H-isoindole-1,3(2H)-dione with molecular bromine in the presence of methanol has given a co-halogenation product, whereas the dibromination product has been obtained in the presence of octyl alcohol.

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Authors and Affiliations

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

    R. N. Khusnitdinov & R. R. Gataullin

  2. Ufa State Petroleum Technical University, Ufa, Russia

    R. M. Sultanov

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  1. R. N. Khusnitdinov
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Khusnitdinov, R.N., Sultanov, R.M. & Gataullin, R.R. Functiaonalization of 2-(1-Cyclohexen-1-yl)aniline Derivatives. Russ J Gen Chem 89, 653–662 (2019). https://doi.org/10.1134/S1070363219040030

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