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Synthesis of 3-(4-Oxo-4H-3,1-benzoxazin-2-yl)-1-benzenesulfonyl Chloride and Its Reactivity toward Amines

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Abstract

3-(4-Oxo-4H-3,1-benzoxazin-2-yl)-1-benzenesulfonyl chloride was synthesized, and reactivity of its functional groups was studied. Reactions of the title compound with equimolar amounts of aniline and piperidine gave the corresponding sulfonamides with retention of the benzoxazine moiety. The same reactions with excess amine resulted in opening of the oxazine ring and formation of o-(m-aminosulfonylbenzoylamino)benzamides.

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Authors and Affiliations

  1. Yaroslavl State Technical University, Moskovskii pr. 88, Yaroslavl', 150023, Russia

    A. V. Tarasov, O. N. Strikanova, Yu. A. Moskvichev & G. N. Timoshenko

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  1. A. V. Tarasov
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  2. O. N. Strikanova
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  3. Yu. A. Moskvichev
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  4. G. N. Timoshenko
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Tarasov, A.V., Strikanova, O.N., Moskvichev, Y.A. et al. Synthesis of 3-(4-Oxo-4H-3,1-benzoxazin-2-yl)-1-benzenesulfonyl Chloride and Its Reactivity toward Amines. Russian Journal of Organic Chemistry 38, 87–89 (2002). https://doi.org/10.1023/A:1015358809887

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  • DOI: https://doi.org/10.1023/A:1015358809887

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