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Synthesis of Atropisomeric Benzoxazocines Based on Etherification Products of N-[2-(Cycloalk-1-en-1-yl)­phenyl]sulfonamides with Ethylene Chlorohydrin

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Abstract

The reactions of N-[2-(cyclohex-1-en-1-yl)-6-methylphenyl]arenesulfonamides and N-[2-(cyclohex-1-en-1-yl)phenyl]methanesulfonamide with molecular bromine in the presence of ethylene chlorohydrin afforded mixtures of N-{2-[6-(2-chloroethoxy)cyclohex-1-en-1-yl]phenyl} sulfonamides and 9-(arenesulfonyl)- or 9-(methanesulfonyl)-2,3,9,9a-tetrahydro-1H-carbazoles. Intramolecular condensation of the obtained 2-chloro­ethyl ethers in the presence of potassium hydroxide and benzyl(triethyl)ammonium bromide in THF gave 8-(arenesulfonyl)-9-methyl-2,4,4a,6,7,8-hexahydro-3H-dibenzo[e,g][1,4]oxazocines as a result of forma­tion of new nitrogen–carbon bond. The presence of a methyl group at C9 of the aromatic ring gives rise to axial isomerism of the synthesized benzoxazocines. The major conformer of the cyclocondensation products has aS*,R* configuration of the heterocycle, and this conformer slowly isomerizes to the aR*,R* conformer at room temperature.

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ACKNOWLEDGMENTS

The spectral studies were performed using the facilities of joint center at the Ufa Institute of Chemistry, Russian Academy of Sciences.

Funding

The study was carried out according to the program “New Approaches and Improvement of Known Strategies for Target-Oriented Synthesis of Poly-, Bi-, and Monocyclic N,N-, N,O-, and S,O-Heterocycles with the Identification of Their Biological and Anticorrosion Activities and Develop­ment of Technologies for Practical Application of the Obtained Compounds with Appropriate Properties” (state assignment reg. no. EGISU 122031400274-4).

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

    R. R. Gataullin

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Correspondence to R. R. Gataullin.

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Gataullin, R.R. Synthesis of Atropisomeric Benzoxazocines Based on Etherification Products of N-[2-(Cycloalk-1-en-1-yl)­phenyl]sulfonamides with Ethylene Chlorohydrin. Russ J Org Chem 59, 2157–2166 (2023). https://doi.org/10.1134/S1070428023120138

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