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Some reactions of 2-chloro-3-(β-chloroethyl)-4,6-dihydroxypyridine

Synthesis of derivatives of 5-azabenzofuran

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The chemical properties of 2-chloro-3-(β-chloroethyl)-4,6-dihydroxypyridine (I) have been studied. It has been shown that this compound, which is relatively stable in acids and in neutral and, particularly, in alkaline media, readily splits off hydrogen chloride under mild conditions and is converted into derivatives of 2, 3-dihydro-5-azabenzofuran. The dehalogenation of I in an acid medium yielded 3-(β-chloroethyl)-4, 6-dihydroxypyridine, which was converted into 4, 6-dichloro-3-(β-chloroethyl)pyridine and into 6-chloro-4-methoxy-3-vinylpyridine.

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References

  1. L. N. Yakhontov, M. Ya. Uritskaya, and M. V. Rubtsov, KhGS [Chemistry of Heterocyclic Compounds], 918, 1965.

  2. S. J. Davis, J. A. Elvidge and A. B. Foster, J. Chem. Soc., 3638, 1962.

  3. L. N. Yakhontov, E. I. Lapan, and M. V. Rubtsov, KhGS [Chemistry of Heterocyclic Compounds], 1063, 1967.

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Yakhontov, L.N., Uritskaya, M.Y., Lapan, E.I. et al. Some reactions of 2-chloro-3-(β-chloroethyl)-4,6-dihydroxypyridine. Chem Heterocycl Compd 4, 14–17 (1970). https://doi.org/10.1007/BF00478066

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  • DOI: https://doi.org/10.1007/BF00478066

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