SYNTHESIS OF SUBSTITUTED COUMARINS AND THEIR CARBORANE DERIVATIVES AS POTENCIAL ANTICANCER DRUGS

Abstract

In this paper, we present the reactions of the conjugated addition of C-metal derivative of boron-rich compound – lithium-o-carborane to the coumarins: 3-acetylbromcoumarin, 3-carbethoxycoumarin and products of its substitution with aromatic nitrogen-containing compounds. Getting the latter was performed here for the first time; the dependence of the reaction direction on the basicity of the amine was shown – the low basic amine (indole) is attached to the 4-position of 3-carbethoxycoumarin, while the more basic amines (aniline and 2-amino-6-methylpyridin) led to obtainment of the classical carboxamides. These initial compounds were introduced into the reaction of conjugated addition with isopropyl lithium-o-carborane. There are row of the products of this interaction: 3-indolo-3-carbonyl-4-(isopropyl-o-carborane)-3,4-dihydrocoumarin, 3-(2-amino-6methylpyridino)-3-carbonyl-4-(isopropyl-o-carboran)-3,4-dihydrocoumarin and 3-anilino3-carbonyl-4-(isopropyl-o-carboran)-3,4-dihydrocoumarin. Reaction of 3-acetylbromcoumarin with lithium-o-carborane in equivalent amount gives 3-carbonyl-3-isopropyl-o-carboranoyl coumarin; whereas two amount of isopropyl lithium-o-carborane leads to the 3-carbonyl-3-isopropyl-o-carboranoyl-4-(isopropyl-o-carborane)-3,4-dihydrocoumarin.

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