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One-pot thioimidoester-mediated synthesis of trans- -a-atlantone

When R2 was a methallyl group a mixture of conjugated and unconjugated ketones was obtained. Treatment by DBU or piperidine yielded the conjugated ketone. The last example in Table 4.2 corresponds to ar-turmerone. [Pg.117]

In the following scheme some promising reactions of metallated imidothioesters are noted aldolization and acylation [384], [Pg.117]

When R is an alkyl group, the p-oxodithioesters available through sulfhydrolysis of the acylation products could not be prepared either by direct condensation of carbon disulfide on a ketone or via oxidation of the 3-hydroxy dithioesters formed in the aldolization reaction of enethiolates (see Section 4.2.4). [Pg.118]

Remark. The procedure described in Section 2.8.3 for the synthesis of N-phenyl imidothioesters gave poor results in the case of methylmagnesium iodide, mainly because of low stability of its addition product to phenyl isothiocyanate. A good yield could be secured by running the reaction at a lower temperature in ether as the solvent and addition of HMPA in the methylation step. Filtration on a very short column of silica (eluent petroleum ether/ethyl acetate 97.5 2.5) afforded a quite pure product in a 79% yield. [Pg.118]


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A-Atlantone

Atlantone

Of trans

One-pot synthesis

Trans synthesis

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