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Investigation of the Regio- and Stereochemistry of the [2+4] Cyclocondensation 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

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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.

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Authors and Affiliations

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

    O. V. Gulyakevich, V. G. Zaitsev & A. L. Mikhal'chuk

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  1. O. V. Gulyakevich
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  2. V. G. Zaitsev
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  3. A. L. Mikhal'chuk
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Gulyakevich, O.V., Zaitsev, V.G. & Mikhal'chuk, A.L. Investigation of the Regio- and Stereochemistry of the [2+4] Cyclocondensation 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. Chemistry of Heterocyclic Compounds 39, 901–910 (2003). https://doi.org/10.1023/A:1026198405363

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