An x-ray crystal structure analysis found that the bromination of methyl 1-allyl-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate by Br2 in glacial HOAc involved not heterocyclization but classical addition of Br2 to the unsaturated allyl bond, in contrast with structurally similar alkyl 1-allyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylates. Pharmacological tests showed that removal of the double bond from the 1-N-alkyl moiety in the esters was associated with a decrease of analgesic activity.
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Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 49, No. 8, pp. 25 – 28, August, 2015.
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Ukrainets, I.V., Petrushova, L.A. & Bereznyakova, N.L. Effect of Bromination on the Pharmacological Properties of Methyl 1-Allyl-4-Hydroxy-2,2-Dioxo-1H-2λ6,1- Benzothiazine-3-Carboxylate. Pharm Chem J 49, 519–522 (2015). https://doi.org/10.1007/s11094-015-1319-4
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DOI: https://doi.org/10.1007/s11094-015-1319-4