Tytuł artykułu
Identyfikatory
Warianty tytułu
Języki publikacji
Abstrakty
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).
Wydawca
Czasopismo
Rocznik
Tom
Strony
1419--1424
Opis fizyczny
Bibliogr. 20 poz., rys.
Twórcy
autor
- Department of Organic Chemistry, Ivan Franko National University of Lviv,Kyryla and Mefodiya 6, 79005 Lviv, Ukraine
autor
- Department of Organic Chemistry, Ivan Franko National University of Lviv,Kyryla and Mefodiya 6, 79005 Lviv, Ukraine
autor
- Department of Organic Chemistry, Ivan Franko National University of Lviv,Kyryla and Mefodiya 6, 79005 Lviv, Ukraine
Bibliografia
- 1. Synthesis of Heterocycles on the Basis of Arylation Products of Unsaturated Compounds. Part 8. Obushak M.D., Matiychuk V.S. and Martyak R.L., ARKIVOC (2002), in press.
- 2. Kutyrev A.A. and Moskva V.V., Usp. Khim., 60, 134 (1991).
- 3. Grinev A.N. and Terent'ev A.P., Zh. Obshch. Khim., 28, 78 (1958).
- 4. Grinev A.N., Pan Bon-Khvar, Frosin V.N. and Terent’ev A.P., Zh. Obshch. Khim., 26, 561 (1956).
- 5. McPherson H.L. and Ponder B.W., J. Heterocycl. Chem., 15, 43 (1978).
- 6. Grinev A.N., Venevtseva N.K. and Terent’ev A.P., Zh. Obshch. Khim., 28, 1850 (1958).
- 7. Kornilov M.Yu., Makovetskii V.P., Turov A.V. and Dzvinchuk I.E., Khim. Geterotsikl. Soedin., 22 (1980).
- 8. Jeffreys J.A.D., J. Chem. Soc., 2153 (1959),
- 9. Fumagalli S.E. and Eugster C.H., Helv. Chim. Acta, 54, 959 (1971).
- 10. Kucktänder U., Herweg-Wahl U., Massa W. and Baum G., Chem. Ber., 120, 1791 (1987).
- 11. Kuckländer U., Herweg-Wahl U., Poll W. and Rickerich L., Chem. Ber., 121, 1841 (1988).
- 12. Derkosch J. and Specht I., Monatsh. Chem., 92, 542 (1961).
- 13. Napier R.J., Shand C.A., Thomson R.H., Cheng L., Griffiths J. and Greenhalgh C.W., J. Chem. Res. Miniprint, 480 (1983).
- 14. Obushak M.D., Matiychuk V.S. and Martyak R.L., Khim. Geterotsikl. Soedin., 986 (2001).
- 15. Brassard R and L’Ecuyer P., Can. J. Chem., 36, 700 (1958).
- 16. Kvalnes D.E., J. Am. Chem. Soc., 56, 2478 (1934).
- 17. Christoffers J., Synlett, 6, 723 (2001).
- 18. King T.J. and Newall C.E., J. Chem. Soc., 974 (1965).
- 19. Makovetskii V.P., Dzvinchuk I.B., Yaremenko V.V. and Svishchuk A.A., Ukrainian Khim. Zh., 45, 652 (1979).
- 20. Makovetskii V.P., Dzvinchuk I.B., Volovenko Yu.M. and Svishchuk A.A., Khim. Geterotsikl. Soedin., 129(1979).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ1-0021-0006