ChemInform Abstract: Synthesis and Antimicrobial Activity of Hydrogenated 2-Acetylindan-1,3-diones.

✍ Scribed by O. P. Shestak; V. L. Novikov; S. I. Stekhova

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 40 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199910109

✦ Synopsis

Synthesis and Antimicrobial Activity of Hydrogenated 2-Acetylindan-1,3-diones.

-Cycloaddition of β,β'-diketones (I) with 1,3-dienes (II), (VII) and (XIII) affords the corresponding tetrahydroindandiones (III), (X), (XIV) and (XVI) -(XIX), resp., in good yields. With monobromo analogue (IV), however, a spontaneous oxidation of the adducts to dihydroindandiones (V), (VIII) and indandiones (VI), (IX) takes place. Cycloaddition of vinylcyclohexene derivatives (VII) and (XIII) proceeds with cis-stereospecificity. However, while the adduct (Xb) is obtained in ortho-regiospecificity, adducts (XVI) -(XIX) are mixtures of regioisomers. All prepared compounds are tested for their antimicrobial activity. Best activity is observed for the dihydroindandiones (V) and (VIII). It is shown, that a shift of the double bond from C(5)-C(6) in compound (Xa) to C(4)-C(5) in compound (XI) enhances the biological activity, while thermal deacetylation to compound (XII) decreases the activity.