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Methyl ester of 4-bromo-3-butyn-1-oic acid, preparation and reaction of nucleophilic addition of amines

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Conclusions

  1. 1.

    It was found that the methyl ester of 4-bromo-3-butyn-1-oic acid is capable of facile prototropic isomerization to the ester of 4-bromo-2,3-butadien-1-oic acid.

  2. 2.

    The transformations of the bromoallenic ester in the reactions with either primary or secondary amines proceed as nucleophilic addition reactions to the central carbon atom of the aliene group.

  3. 3.

    A general method was developed for the synthesis of the previously unknown N-alkyl-2,4-pyrroli-dinedione enamines.

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1763–1769, August, 1972.

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Mavrov, M.V., Kucherov, V.F. Methyl ester of 4-bromo-3-butyn-1-oic acid, preparation and reaction of nucleophilic addition of amines. Russ Chem Bull 21, 1706–1711 (1972). https://doi.org/10.1007/BF00851184

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Keywords

  • Methyl
  • Ester
  • Carbon Atom
  • Methyl Ester
  • Secondary Amine