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Reactions of enamino keto esters of 1,2,3,4-tetrahydroisoquinoline series with nucleophiles

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Chemistry of Heterocyclic Compounds Aims and scope

It has been shown that the reaction of the methyl ester of 3-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-idene)pyruvic acid with thiosemicarbazide in glacial acetic acid leads to heterocyclization with the formation of 3,3-dimethyl-1-(5-thioxo-1,5-dihydro-1,2,4-triazol-3-ylmethylidenecarbonyl)-1,2,3,4-tetra-hydroisoquinoline, but the interaction with semicarbazide under the same conditions leads to annelation of the pyrrole ring. On condensation of the enamino keto ester with malonodinitrile, the nitrile of 2-cyano-4-dicyanomethylidene-5-(3,3-dimethyl-1,2,3.4-tetrahydroisoquinolin-1-idene)-3-oxo-pentanoic acid is formed.

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Notes

  1. *Here and subsequently values of m/z (Irel, %) are given for peaks.

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, Perm, 614990, Russia

    O. V. Surikova, A. G. Mikhailovskii & M. I. Vakhrin

Authors
  1. O. V. Surikova
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  2. A. G. Mikhailovskii
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  3. M. I. Vakhrin
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Correspondence to A. G. Mikhailovskii.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 221-226, February, 2010.

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Surikova, O.V., Mikhailovskii, A.G. & Vakhrin, M.I. Reactions of enamino keto esters of 1,2,3,4-tetrahydroisoquinoline series with nucleophiles. Chem Heterocycl Comp 46, 179–183 (2010). https://doi.org/10.1007/s10593-010-0489-y

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  • DOI: https://doi.org/10.1007/s10593-010-0489-y

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