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Regioselective syntheses of α-functionally substituted ketones

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The reduction of 2,2-dimethyl-4,6-dioxo-5-hydroxyimino-1,3-dioxane with Zn in an AcOH/Ac2O mixture gives 2,2-diniethyl-4,6-dioxo-5-acetamido-1,3-dioxane, the cleavage of which with aqueous AcOH leads to N-acetylglycine.

  2. 2.

    The chlorination of the 5-acyl derivatives of Meldrum's acid with SO2Cl2 and subsequent hydrolytic cleavage of the intermediate 2,2-dimethyl-4,6-dioxo-5-chloro-5-acyl-1,3-dioxanes by aqueous AcOH give chloromethyl alkyl ketones.

  3. 3.

    The hydrolytic cleavage of the 2,2-dimethyl-4,6-dioxo-5-(N-phthaloyl-α-aminoacyl)-1,3-dioxanes by either aqueous AcOH or HCl leads to eitherα-phthalimido-orα-aminoketones.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    S. I. Zav'yalov, G. I. Ezhova, T. K. Budkova, O. V. Dorofeeva & O. K. Taganova

Authors
  1. S. I. Zav'yalov
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  2. G. I. Ezhova
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  3. T. K. Budkova
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  4. O. V. Dorofeeva
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  5. O. K. Taganova
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 468–471, February, 1982.

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Zav'yalov, S.I., Ezhova, G.I., Budkova, T.K. et al. Regioselective syntheses of α-functionally substituted ketones. Russ Chem Bull 31, 424–427 (1982). https://doi.org/10.1007/BF00948279

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  • DOI: https://doi.org/10.1007/BF00948279

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