Summary
A number of furo[3,2-c]pyridines (4a–4d) and benzo[b]derivative (4e), as well as pyrrolo[2′,3′-4,5]furo[3,2-c]pyridine (8) were prepared by reaction of the corresponding iminophosphoranes, available from ethyl azidoheteroacrylates and triphenylphosphine, with phenyl isocyanate. The appropriate azidoheteroacrylates were used for the preparation of some substituted furo[3,2-b:4,5-b]dipyrroles (6). The reactions of the prepared compounds are described.
Zusammenfassung
Eine Anzahl von Furo[3,2-c]pyridinen (4a –4d), ein Benzo[b]derivat (4e) und Pyrrolo[2′,3′:4,5]furo[3,2-c]pyridin (8) wurden durch die Reaktion von Phenylisocyanaten mit den entsprechenden Iminophosphoranen dargestellt, die aus Ethyl-azidoheteroacrylaten und Triphenylphosphin leicht zugänglich sind. Die entsprechenden Azidoacrylate wurden zur Synthese einiger Furo[3,2-b:4,5-b′]dipyrrole (6) verwendet. Die Reaktionen einiger dieser Verbindungen werden beschrieben.
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References
Hemetsberger H., Knittel D. (1972) Monatsh. Chem.103: 194
Krutosikova A., Kovac J., Kristovak J. (1979) Collect. Czech. Chem. Commun.44: 1799
Krutosikova A., Kovac J., Dandarova M., Veverka M. (1979) Collect. Czech. Chem. Commun.44: 1805
Krutosikova A., Kovac J., Chudobova M., Ilavsky D. (1980) Collect. Czech. Chem. Commun.45: 2940
Krutosikova A., Kovac J., Dandarova M., Lesko J., Ferik S. (1981) Collect. Czech. Chem. Commun.46: 2564
Krutosikova A., Kovac J., Kralovicova E. (1983) Collect. Czech. Chem. Commun.48: 772
Krutosikova A., Kovac J., Kralovicova E. (1983) Collect. Czech. Chem. Commun.48: 1878
Krutosikova A., Kovac J., Dandarova M. (1984) Collect. Czech. Chem. Commun.49: 65
Krutosikova A., Kovac J., Banak P. (1984) Chem. zvesti38: 707
Korenova A., Krutosikova A., Dandarova M., Kovac J. (1984) Collect. Czech. Chem. Commun.49: 1529
Kralovicova E., Krutosikova A., Kovac J., Dandarova M. (1986) Collect. Czech. Chem. Commun.51: 106
Krutosikova A., Kralovicova E., Dandarova M., Kelemen P. (1988) Chem. Papers42: 89
Fisera L., Dandarova M., Kovac J., Mesko P., Krutosikova A. (1981) Collect. Czech. Chem. Commun.46: 2421
Dandarova M., Krutosikova A., Alföldi J., Kovac J. (1988) Chem. Papers43: 457
Krutosikova A., Dandarova M., Alföldi, J., Kovac J. (1988) Collect. Czech. Chem. Commun.53: 1770
Fridrichsen W. (1984) In: Katritzky A. R., Rees C. W. (eds.) Comprehensive Heterocyclic Chemistry, Vol. 4. Pergamon Press, Oxford, p. 1037
Eloy F., Deryckere A. (1971) J. Heterocycl. Chem.8: 57
Bouzard J. D., Bisagni E. (1971) Bull. Soc. Chim. Fr.: 1727
Lhommet G., Sliwa H., Maitte P. (1972) Bull. Soc. Chim. Fr.: 1442
Molina P., Fresneda P. M., Hurtado F. (1987) Synthesis: 45
Mc Farland J. W., Essay W. A., Cilenti L., Cozard W., Mc Farland P. E. (1975) J. Heterocycl. Chem.12: 75
Korenova A., Krutosikova A., Kovac J., Celec S. (1987) Collect. Czech. Chem. Commun.52: 192
New J.S., Christopher W. L., Yevich J. P., Butler R., Schlemmer Jr. R. F., Vander Maelen C. P., Cipollina J. A. (1989) J. Med. Chem.32: 1147
Krutosikova A., Kovac J., Dandarova M., Bobalova M. (1982) Collect. Czech. Chem. Commun.47: 3288
Krutosikova A., Hanes M. (1992) Collect. Czech. Chem. Commun.57: (in press)
Ho C. Y., Hageman W. E., Persico F. J. (1986) J. Med. Chem.29: 1118
Frimm. R., Kovac J., Krutosikova A. (1973) Chem. zvesti27: 101
Vegh D., Zalupsky P., Kovac J. (1990) Synth. Commun.20: 1113
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Krutosikova, A., Dandarova, M., Chylova, J. et al. Condensed O-, N-heterocycles by the transformation of azidoacrylates. Monatsh Chem 123, 807–815 (1992). https://doi.org/10.1007/BF00812330
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DOI: https://doi.org/10.1007/BF00812330