Synthesis of 2-aroyl- and (2-oxo-2H-4-chro menyl) furo[3,2-g]neoflavones
DOI:
https://doi.org/10.15407/dopovidi2019.11.066Keywords:
2-g]neoflavones, 4-chloromethylcoumarins, 6-аcetyl-7-hydroxyneoflavones, furo[3, heterocyclization, phenacyl bromidesAbstract
This paper is devoted to the development of a practical and effective synthesis technique for 2-aroylfuro[3,2-g] chromen-7-ones and 2-(2-oxo-2H-4-chromenyl)furo[3,2-g]chromen-7-ones that are modified analogs of natural furocoumarin psoralen. The interaction of 6-acetyl-7-hydroxy-8-methylchro men-2-ones with phenacylbromides and 4-chloromethylcoumarins in dimethylformamide in the presence of K2CO3 upon heating is stu died. 2-Aroylfuro[3,2-g]chromen-7-ones were obtained in one step in good yields as a result of simultaneous alkylation of 6-acethyl-7-hydroxy-8-methylchromen-2-ones by corresponding phenacylbromides followed by condensation of carbonyl group. The use of 1-benzo[b]furan-2-yl-2-bromo-1-ethanone in this heterocyclization was completed by the formation of 2-(ben zofuran-2-carbonyl)-3,9-dimethyl-5-phenyl-7H-furo[3,2-g]chromen-7- one. As a result of the interaction of 6-ace tyl-7-hydroxy-8-methylneoflavone with 4-chloromethylcoumarins under the conditions developed by us, 2-coumarinyl-5-phenyl-7H-furo[3,2-g]chromen-7-ones with coumarin substituent in the second position were obtained in good yields. The structure of the obtained compounds was proved using the methods of NMR spect roscopy. The obtained compounds are promising both for medical chemistry and for subsequent synthetic transformations, as well as for the study of their physico-chemical properties and structural features.
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