INVESTIGATION OF THE REGIO- AND STEREOCHEMISTRY OF THE [2+4] CYCLO-CONDENSATION OF 3,4-DIHYDROISOQUINOLINES WITH 2-ACETYL-4-HYDROXYCYCLOHEXANE-1,3-DIONE. SYNTHESIS AND PROPERTIES OF THE REGIOISOMERIC 15- AND 17-HYDROXY DERIVATIVES OF 8-AZA-D-HOMOGONA-12,17a-DIONES

Authors

  • О. В. Гулякевич Institute of Bioorganic Chemistry, National Academy of Sciences of the Republic of Belarus, Minsk 220141
  • В. Г. Зайцев Institute of Bioorganic Chemistry, National Academy of Sciences of the Republic of Belarus, Minsk 220141
  • А. Л. Михальчук Institute of Bioorganic Chemistry, National Academy of Sciences of the Republic of Belarus, Minsk 220141

Keywords:

azomethines, 2-acetyl-4-hydroxycyclohexane-1,3-dione, 3,4-dihydroisoquinolines, Schiff's bases, β,β'-triketones, annelation, regiochemistry, stereochemistry, cyclocondensation

Abstract

The 15- and 17-hydroxy derivatives of 8-aza-D-homogona-12,17a-diones were obtained by the annelation of 3,4-dihydroisoquinolines with 2-acetyl-4-hydroxycyclohexane-1,3-dione. It was shown that the reaction proceeds stereoselectively with the intermediate formation of 9,15- and 9,17-trans isomers. The probable mechanism and certain aspects of the interconnection between the structural and physicochemical characteristics of the obtained compounds are discussed.

How to Cite
Gulyakevich, O. V.; Zaitsev, V. G.; Mikhal'chuk, A. L. Chem. Heterocycl. Compd. 2003, 39, 901. [Khim. Geterotsikl. Soedin. 2003, 1043.]

For this article in the English edition, see DOI https://doi.org/10.1023/A:1026198405363

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Published

2003-07-25

Issue

No. 7 (2003)

Section

Original Papers