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
Keywords:
8-aza-16-thiagona-12,17-diones, 3,4-dihydroisoquinolinium 3-acetylthiotetronate, 3-acylthiotetronic acids, 3,4-dihydroisoquinolines, annelationAbstract
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.
How to Cite
Budnikova, M. V.; Rubinov, D. B.; Mikhal'chuk, A. L. Chem. Heterocycl. Compd. 2002, 38, 929. [Khim. Geterotsikl. Soedin. 2002, 1067.]
For this article in the English edition, see DOI https://doi.org/10.1023/A:1020917429301
