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With potassium carbonate; In water; N,N-dimethyl-formamide; at 20.0℃; for 18.0h;
[00118] Dimethoxycurcumin (8) will be prepared via condensation of 3,4- dimethoxybenzaldehyde and 2,4-pentanedione according to the procedure of Venkateswarlu. Treatment of 8 with potassium carbonate in the presence of a suitable alkylating agent is expected to affect the desired disubstitution reactions. Alkylation with the diiodoalkanes should result in formation of the spirocyclic products.[00119] As noted in Example I, the inventors now prepared derivatives FLLL31 (Ib, R = methyl) and FLLL32 (6b, cyclohexyl) in this way. Interestingly, O-alkylation of the enolate generated from 8 is also observed in both cases, although the yield of this product is relatively low (<;10%) and can be readily separated via column chromatography.
To stirred solution of 7-Azaoxindole 1 (0.5 g ,3.73mmol ) in anhydrous THF(10 ml ) was added n-butyl lithium (0.47g,7.42 mmol)at -78C followed by TMEDA (0.865 g, 7.42mmol ).After lh ,1,5 diiodo pentane( 0.799 g, 3.73 mmol ) was added slowly and mixture was allowed to come up to room temperature. After stirring for 15h, saturated aqueous ammonium chloride was added and the crude material was partitioned between water and ethyl acetate. Organic layer was separated, dried over sodium sulphate and concentrated under vacuum. Crude compound was purified by column chromatography by eluting with 40% ethyl acetate and pet ether to get the desired compound 2 (0.1 g)
0.1 g
Step-1 [0062] To stirred solution of 7-Azaoxindole 1 (0.5 g, 3.73 mmol) in anhydrous THF (10 ml) was added n-butyl lithium (0.47 g, 7.42 mmol) at -78 C. followed by TMEDA (0.865 g, 7.42 mmol). After 1 h, 1,5 diiodo pentane (0.799 g, 3.73 mmol) was added slowly and mixture was allowed to come up to room temperature. After stirring for 15 h, saturated aqueous ammonium chloride was added and the crude material was partitioned between water and ethyl acetate. Organic layer was separated, dried over sodium sulphate and concentrated under vacuum. Crude compound was purified by column chromatography by eluting with 40% ethyl acetate and pet ether to get the desired compound 2 (0.1 g)
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