Bromination of 4-aryl-3,5-dialkoxycarbonyl-2,6-dimethyl-1,4-dihydropyridines |
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Authors: | I. P. Skrastin'sh V. V. Kastron B. S. Chekavichus A. é. Sausin'sh R. M. Zolotoyabko G. Ya. Dubur |
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Affiliation: | (1) Institute of Organic Synthesis, Latvian Academy of Sciences, 226006 Riga |
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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.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1230–1235, September, 1991. |
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