期刊
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
卷 -, 期 22, 页码 3732-3741出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/b004422i
关键词
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A novel approach to the synthesis of C-ring substituted xanthones utilising the [4+2] cycloaddition reactions of enamines with aromatically substituted vinylchromones has been developed. 1-Methyl-, 1-ethyl-, 2-methyl- and 2-ethyl-substituted xanthones are obtained in a one-pot synthesis from the reaction of pyrrolidine enamines derived from acetone, butan-2-one, propanal and butanal respectively, when taken as solvent incorporating a catalytic amount of pyrrolidine. Some 1-methylidene- and 1-methylidene-2-methyl-substituted tetrahydroxanthones were also obtained and these compounds are proposed to be intermediates in the reaction, since they undergo facile conversion to 1-methyl- and 1,2-dimethyl-xanthones. Further evidence for the proposed reaction pathway was obtained from the isolation of a 1-pyrrolidino-2,2-dimethyl substituted tetrahydroxanthone from the reaction between a vinylchromone and the pyrrolidine enamine of 2-methylpropanal.
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