Cyclization reactions leading to beta-hydroxyketo esters
Nicholson, JM; Edafiogho, IO; Moore, JA; Farrar, VA; Scott, KR
| HERO ID | 4923730 |
|---|---|
| In Press | No |
| Year | 1994 |
| Title | Cyclization reactions leading to beta-hydroxyketo esters |
| Authors | Nicholson, JM; Edafiogho, IO; Moore, JA; Farrar, VA; Scott, KR |
| Journal | Journal of Pharmaceutical Sciences |
| Volume | 83 |
| Issue | 1 |
| Page Numbers | 76-78 |
| Abstract | The purpose of the research was to synthesize beta-diketo esters and to evaluate them for anticonvulsant activity. The reaction of methyl vinyl ketone with dimethyl malonate in the presence of potassium carbonate gave an uncyclized product that underwent a Claisen condensation to yield methyl 2-hydroxy-4-oxocyclohex-2-en-1-oate (5a). Similarly, other cyclized beta-hydroxyketo esters were prepared, and their spectrometric data confirmed that the enol tautomers were preferred to the beta-diketo tautomers. The synthetic work clarified the reaction pathway for the Michael addition of malonate esters to enones. Of the intermediates and products tested for anticonvulsant activity, dimethyl 2,2-bis-(3-oxobutyl)malonate (9a) was found to possess anticonvulsant property. However, it is emphasized that the beta-hydroxyketo esters could be useful intermediates in the synthesis of enaminone anticonvulsants. |
| Doi | 10.1002/jps.2600830118 |
| Pmid | 8138915 |
| Wosid | WOS:A1994MP53500016 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |