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Annelation of 3,4-Dihydroisoquinolines with 3-Acylthiotetronic Acids: Synthesis and Properties of 8-Aza-16-thiagona-12,17-diones and 3,4-Dihydroisoquinolinium 3-Acetylthiotetronate

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

8-Aza-16-thiagona-12,17-diones have been obtained by the annelation of C(1)-unsubstituted 3,4-dihydroisoquinolines with 3-acylthiotetronic acids on refluxing in glacial acetic acid. The condensation of 1-methyl-3,4-dihydroisoquinoline with 3-acetylthiotetronic acid stopped at the salt formation stage. From the results of H/D isotopic exchange of 3,4-dihydroisoquinolinium 3-acetylthiotetronate it follows that a tautomeric equilibrium is established for the anion of 3-acetylthiotetronic acid, involving the protons of the acetyl group and the C(5) methylene group of the thiolactone ring in isotopic exchange.

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  1. Institute of Bioorganic Chemistry, National Academy of Sciences of Belarus, Minsk, 220141

    M. V. Budnikova, D. B. Rubinov & A. L. Mikhal'chuk

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  3. A. L. Mikhal'chuk
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Budnikova, M.V., Rubinov, D.B. & Mikhal'chuk, A.L. Annelation of 3,4-Dihydroisoquinolines with 3-Acylthiotetronic Acids: Synthesis and Properties of 8-Aza-16-thiagona-12,17-diones and 3,4-Dihydroisoquinolinium 3-Acetylthiotetronate. Chemistry of Heterocyclic Compounds 38, 929–939 (2002). https://doi.org/10.1023/A:1020917429301

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