Abstract
4-Aryl-3,5-dialkoxycarbonyl-2,6-dimethyl-1,4-dihydropyridines are brominated by N-bromosuccinimide in methanol at room temperature at the methyl groups at positions 2 and 6 to form mono-, di-, tri-, and tetrabromo derivatives. When the N-unsubstituted bromomethyl-1,4-dihydropyridines are heated they are easily converted to tetrahydrofuropyridines, but in the case of the analogous N-substituted-1,4-dihydropyridines cyclization does not occur. The 2,6-bis(bromomethyl)-substituted products easily replace bromine under the influence of nucleophilic reagents.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1230–1235, September, 1991.
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Skrastin'sh, I.P., Kastron, V.V., Chekavichus, B.S. et al. Bromination of 4-aryl-3,5-dialkoxycarbonyl-2,6-dimethyl-1,4-dihydropyridines. Chem Heterocycl Compd 27, 989–994 (1991). https://doi.org/10.1007/BF00484364
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DOI: https://doi.org/10.1007/BF00484364