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Synthesis of Nicotinic Acid Derivatives by the Reaction of Salts of 1-Alkyl-4,6-dimethyl-2-pyrimidinylacetic Acid Esters with Amines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A study was carried out on the enamine rearrangement of iodoalkylates of the ethyl ester of 4,6-dimethyl-2-pyrimidinylacetic acid to give ethyl esters of 2-alkylamino-4,6-dimethylnicotinic acid, which proceeds upon the action of various amines. The reaction with amines containing an alkyl substituent different from that at the quaternized nitrogen atom of the pyrimidinium salt leads to the formation of products of rearrangement and transamination. In the presence of water, the rearrangement is accompanied by the formation of the ethyl ester of 1,2-dihydro-2-oxo-4,6-dimethylnicotinic acid.

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Authors and Affiliations

  1. Yerevan Institute of National Economy, Yerevan, 375025, Republic of Armenia

    G. G. Danagulyan & L. G. Saakyan

  2. Center for the Study of Molecular Structure, National Academy of Sciences of the Republic of Armenia, Yerevan, 375014, Republic of Armenia

    G. A. Panosyan

Authors
  1. G. G. Danagulyan
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  2. L. G. Saakyan
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  3. G. A. Panosyan
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Danagulyan, G.G., Saakyan, L.G. & Panosyan, G.A. Synthesis of Nicotinic Acid Derivatives by the Reaction of Salts of 1-Alkyl-4,6-dimethyl-2-pyrimidinylacetic Acid Esters with Amines. Chemistry of Heterocyclic Compounds 37, 323–328 (2001). https://doi.org/10.1023/A:1017559100450

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  • DOI: https://doi.org/10.1023/A:1017559100450

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