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Regioselectivity of the knorr reaction with 2-formyl- and 2-ethoxyoxalylcyclohexanones

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The reaction of 2-formylcyclohexanone withα-aminoacetoacetic acid ester in acetic acid leads to the formation of 2-carbethoxy-4,5-tetramethylenepyrrole with an admixture of the isomeric 2-carbethoxy-3,4-tetramethylenepyrrole, which is also isolated during the reaction of 2-formylcyclohexanone with aminomalonic acid ester.

  2. 2.

    The condensation of 2-formylcyclohexanone with glycine ethyl ester, followed by the cyclization of the intermediate enamine with acetic anhydride, leads to the formation of 1-acetyl-3,4-tetramethylenepyrrole.

  3. 3.

    The reaction of 2-ethoxyoxalylcyclohexanone withα-aminoacetoacetic acid ester yields 2-carbethoxy-3-carboxy-4,5-tetramethylenepyrrole.

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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 & T. I. Skoblik

Authors
  1. S. I. Zav'yalov
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  2. T. I. Skoblik
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 12, pp. 2768–2771, December, 1977.

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Zav'yalov, S.I., Skoblik, T.I. Regioselectivity of the knorr reaction with 2-formyl- and 2-ethoxyoxalylcyclohexanones. Russ Chem Bull 26, 2559–2562 (1977). https://doi.org/10.1007/BF00924565

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  • DOI: https://doi.org/10.1007/BF00924565

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