Abstract
Three-ring systems with benzo[b]furan, benzo[b]selenophene, and benzo[b]thiophene rings condensed with the pyridine ring and with a methyl group in the α position of the pyridine ring were synthesized by the reaction of 2-chloro-3-nitro-6-methylpyridine with sodium phenoxide, sodium thiophenoxide, or sodium selenophenoxide, reduction of the resulting 2-phenoxy-, 2-phenylthio-, and 2-phenylseleno-3-nitro-6-methylpyridines with stannous chloride in concentrated hydrochloric acid, diazotization of the substituted 3-aminopyridines, and heating of the diazonium compounds in 25% sulfuric acid.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1541–1543, November, 1972.
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Abramenko, P.I., Zhiryakov, V.G. Synthesis of methyl-substituted benzofuro-, benzothieno-, and benzoselenopheno[2,3-b]pyridines. Chem Heterocycl Compd 8, 1392–1394 (1972). https://doi.org/10.1007/BF00471880
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DOI: https://doi.org/10.1007/BF00471880