HETEROCYCLIC ANALOGS OF 5,12-NAPHTHACENEQUINONE 8. SYNTHESIS OF FURANO-ANTHRAQUINONES

作者：Shchekotikhin A E^*; Luzikov Yu N; Buyanov V N; Preobrazhenskaya M N

来源：Chemistry of Heterocyclic Compounds, 2009, 45(2): 151-160.

DOI：10.1007/s10593-009-0244-4

• anthra[2,1-d][1,3]dioxole-6,11-dione
• anthra[2,3-b]furan-5,10-dione
• anthra[1,2-b]furan-6,11-dione
• anthra[1,3-b]furan-2,6,11(3H)-trione
• 2,3-dichloroquinizarine
• methyl pivaloylacetate
• condensation
• modification

During the condensation of 2,3-dichloroquinizarine with methyl pivaloylacetate in the presence of potassium carbonate in dimethyl sulfoxide the main reaction products are derivatives of angular 3-pivaloylanthra[1,2-b]furan-2,6,11(3H)-trione (about 70%) and anthra[2,1-d][1,3]dioxole-6,11-dione (15%), whereas the yield of the targeted linear methyl 2-tert-butyl-4,11-dihydroxyanthra[2,3-b]furan-5,10-dione-3-carboxylate is only 2%. Methods are developed for modification of the obtained 3-pivaloylanthra[1,2-b]furan-2,6,11(3H)-trione, making it possible to use it for the synthesis of the tertbutyl derivatives of linear anthra[2,3-b]furan-5,10-dione or angular anthra[1,2-b]furan-6,11-dione.

• 出版日期2009-2