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1 Polish Journal of Chemistry

1 2002

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Synthesis of Heterocycles on the Basic of Arylation Products of Unsaturated Compounds. Part 9. Dialkyl 2,6-Diamino-4-arylfuro[2',3':4,5]benzo[b]furan-3,7-dicarboxylates from 2-Aryl-1,4-benzoquinones and Cyanoacetic Esters

Obushak M., R.L. Martyak R.L., Matiychuk V. S.

Polish Journal of Chemistry

2002

Vol. 76 / nr 10

1419-1424

2-Aryl-1,4-benzoquinones 1a-h (aryl = RC6H4, R = H, 4-Me, 3-CF3, 4-COOH, 3-Cl, 4-Cl, 4-F, 4-NO2) react with methyl 2a and ethyl 2b cyanoacetates in the presence of some bases to form dialkyl 2,6-diamino-4-arylfuro[2_,3_:4,5]benzo[b]furan-3,7-dicarboxylates 3a-l. Regardless of the reagents ratio benzodifuran derivatives are formed selectively. Only in reaction of 2-(4-nitrophenyl)-1,4-benzoquinone 1h with 2b ethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzo[b]furan-3-carboxylate 4 is formed as minor component besides of 3l. Starting compounds 1a-h are prepared by arylation of the 1,4-benzoquinone with arenediazonium chlorides (Meerwein reaction).