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Synthesis of substituted 2-aroyl-3-methylchromen-4-ones from isovanillin via 2-aroyl-3-methylchroman intermediates |
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| Authors: | Sie-Rong Li Liang-Yeu Chen Hsing-Ming Chen Eng-Chi Wang |
| Institution: | a Faculty of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC b Graduate Institute of Pharmaceutical Sciences, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC c Department of Nutrition and Health science, Fooyin University, Kaohsiung 831, Taiwan, ROC |
| Abstract: | The synthesis of substituted 2-aroyl-3-methylchromen-4-one from isovanillin is described. O-Allylphenol (2) prepared from isovanillin (1) was allowed to react with various α-bromoacetophenone (3) to produce 2-(2-allyl-3,4-dimethoxy)phenoxy-1-aroylethanones (4). The resultant 4 were treated with 2 equiv of potassium tert-butoxide to afford the substituted 2-aroyl-3-methylchromans (5) through an isomerization of an allylic double bond and a carbanion-olefin intramolecular 6-endo-trig cyclization reaction. Subsequently, resultant 5 were oxidized with DDQ to yield the title compound 6, in good over-all yields. |
| Keywords: | Carbanion-olefin intramolecular cyclization 3 4-Dihydro-2H-benzopyrans DDQ 2-Aroyl-3-methylchromen-4-ones Isovanillin |
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