The cyclization of N-chloro-N-(2-phenylethoxy)urea in the presence of silver trifluoroacetate leads to the formation of 3,4-dihydro-1H-2,1-benzoxazine-1-carboxamide, while N-alkoxy-N'-aryl-N-chloro-ureas in the presence of sodium acetate form 1-alkoxy-1,3-dihydrobenzimidazol-2-ones. The structures of 3,4-dihydro-1H-2,1-benzoxazine-1-carboxamide and 1-methoxy-6-nitro-1,3-dihydrobenzimidazol-2-one were examined by X-ray structural analysis.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1282-1293, August, 2013.
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Shtamburg, V.G., Shishkin, O.V., Shtamburg, V.V. et al. N-Alkoxy-N-chloroureas in the synthesis of 3,4-dihydro-1H-2,1-benzoxazine-1-carboxamide and 1-alkoxy-1,3-dihydrobenzimidazol-2-ones. Chem Heterocycl Comp 49, 1195–1206 (2013). https://doi.org/10.1007/s10593-013-1363-5
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DOI: https://doi.org/10.1007/s10593-013-1363-5