Conclusions
The direction of reaction and the composition and yields of products obtained by reaction of the Na salt of p-toluenesulfonamide with N-(ω-bromoalkyl)uracils depend primarily on the length of the alkyl chain in the latter: When the Na salt of p-toluenesulfonamide reacts with N-(ω-bromopropyl)-6-methyluracil, the latter undergoes intramolecular cyclization, whereas the Na salt of p-toluenesulfonamide undergoes intermolecular alkylation at the sulfonamide group on reaction with N-(ε-bromopentyl)-6-methyluracil. In analogous reactions, N-(ω-bromobutyl)uracils undergo both intramolecular cyclization, followed by opening of the oxazepine ring by nucleophilic reagents, and intermolecular alkylation.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2079–2084, September, 1978.
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Shvetsov, Y.S., Shirshov, A.N. & Reznik, V.S. Synthesis and properties of pyrimidinylalkylsulfonamides 4. Reaction of the Na salt of p-toluenesulfonamide with mono-N-(ω-haloalkyl)uracils. Russ Chem Bull 27, 1833–1837 (1978). https://doi.org/10.1007/BF00929233
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DOI: https://doi.org/10.1007/BF00929233