One-Pot Synthesis of B-Ring Ortho-Hydroxylated Sappanin-Type Homoisoflavonoids.
| Autor: | Mrug GP; Department of Chemistry of Bioactive Nitrogen-Containing Heterocyclic Bases, V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry , National Academy of Science of Ukraine , Kyiv 02094 , Ukraine., Myshko NV; Institute of High Technologies , Taras Shevchenko Kyiv National University , Kyiv 03022 , Ukraine., Bondarenko SP; Department of Food Chemistry , National University of Food Technologies , Kyiv 01601 , Ukraine., Sviripa VM, Frasinyuk MS; Department of Chemistry of Bioactive Nitrogen-Containing Heterocyclic Bases, V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry , National Academy of Science of Ukraine , Kyiv 02094 , Ukraine. |
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| Jazyk: | angličtina |
| Zdroj: | The Journal of organic chemistry [J Org Chem] 2019 Jun 07; Vol. 84 (11), pp. 7138-7147. Date of Electronic Publication: 2019 May 24. |
| DOI: | 10.1021/acs.joc.9b00814 |
| Abstrakt: | A reliable method for the synthesis of B-ring hydroxylated homoisoflavonoids and 3-hetarylmethyl chromones has been developed. The method involves an initial oxa-Diels-Alder reaction of ortho-quinone methides generated from aryl/hetaryl-substituted ortho-( N, N-dimethylaminomethyl)phenols with (2 E)-3-( N, N-dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-ones and the subsequent cascade of reactions. This synthetic strategy avoids conventional multistep protocols and does not require the protection of hydroxyl groups, thus allowing the facile synthesis of a library of various aromatic and heterocyclic analogues of naturally occurring homoisoflavonoids. |
| Databáze: | MEDLINE |
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