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Synthesis of heterocyclic systems with carbohydrate fragment

2. Stereoselective synthesis of tetrahydropyridones by reaction of levoglucosenone with amides of α-methylene-active acids

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

The reactions of levoglucosenone with amides of several α-nitrocarboxylic acids and acetoacetic acid result in tetra hydropyridones fused with a carbohydrate fragment. In the case of acetoacetic acid amides, mixtures of keto and enol tautomers were obtained. The stereochemistry of cyclization is discussed in detail.

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Authors and Affiliations

  1. Russian Academy of Sciences, N. D. Zelinsky Institute of Organic Chemistry, 47 Leninsky prosp., 117913, Moscow, Russia

    A. V. Samet, Y. P. Kislyi, N. B. Chernyshova, D. N. Reznikov, B. I. Ugrak & V. V. Semenov

Authors
  1. A. V. Samet
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  2. Y. P. Kislyi
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  3. N. B. Chernyshova
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  4. D. N. Reznikov
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  5. B. I. Ugrak
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  6. V. V. Semenov
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Additional information

For Communication 1, see Ref. 1.

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 409–414, February, 1996.

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Samet, A.V., Kislyi, Y.P., Chernyshova, N.B. et al. Synthesis of heterocyclic systems with carbohydrate fragment. Russ Chem Bull 45, 393–398 (1996). https://doi.org/10.1007/BF01433979

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  • DOI: https://doi.org/10.1007/BF01433979

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