Summary
The reactivity of cyanomethylene-indolones (1 a–e) and 2-(dicyanomethylene)-indan-1,3-dione (4) towards 1,5-disubstituted 3-pyrazolones (2 a–c) was investigated. The reactions yield spiro[indene- and spiro[indole-4′- and 6′-pyrano[2,3-c]pyrazoles] (3 a–e,5 a–c). The structures are proven by13C-NMR-spectroscopy. The mechanisms of the reactions are discussed.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
Literatur
87. Mitt.: Reidlinger G. H., Junek H. (im Druck) Synthesis
Sterk H., Junek H. (1970) Tetrahedron26: 5361
Aigner H., Junek H., Sterk H. (1970) Monatsh. Chem.101: 1145
Junek H., Aigner H., Fischer-Colbrie H. (1972) Monatsh. Chem.103: 639
Fischer-Colbrie H., Aigner H., Junek H. (1975) Monatsh. Chem.106: 742
Junek H., Hermetter A., Fischer-Colbrie H., Aigner H. (1973) Tetrahedron Lett.1973: 2993
Junek H., Fischer-Colbrie H., Hermetter A. (1977) Z. Naturforsch.B 32: 898
Dworczak R., Sterk H., Kratky C., Junek H. (1989) Ber. Dtsch. Chem. Ges.122: 1323
Joshi K. C., Jain R., Chand P. (1985) Heterocycles23: 957
Schönberg A., Singer E. (1971) Ber. Dtsch. Chem. Ges.104: 160
Schönberg A., Singer E., Eschenhof B. (1978) Ber. Dtsch. Chem. Ges.111: 3058
Möhrle H., Dörnbrack S., Novak H.-J. (1981) Monatsh. Chem.112: 1417
Schmidt R. R., Vogt K. (1983) Synthesis1983: 199
Hug R., Hansen N. J., Schmid H. (1969) Chimia23: 108
Roedig A., Renk H. A., Schaal V., Scheutzow D. (1974) Ber. Dtsch. Chem. Ges.107: 1136
Strohmeier W., Eder E. (1974) Z. Naturforsch.B 29: 282
Junek H., Dworczak R., Sterk H., Fabian W. (1989) Liebigs Ann. Chem.1989: 1065
Junek H., Sterk H. (1968) Tetrahedron Lett.1968: 4309
Biquard D., Grammaticakis P. (1941) Bull. Soc. Chim.8: 246
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Dworczak, R. Synthesen mit Nitrilen, 88. Mitt.: Spiro[indol- und Spiro[inden-pyrano[2,3-c]pyrazole]aus Cyanmethylenderivaten und Pyrazolonen. Monatsh Chem 122, 731–737 (1991). https://doi.org/10.1007/BF00811473
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00811473