Summary
An improved procedure for the synthesis of several isomeric methoxynitronaphthalenes is described. The key intermediates in the synthesis are the respective nitronaphthylamines and nitronaphthols. The syntheses of 1-methoxy-3-nitronaphthalene (1), 1-methoxy-5-nitronaphthalene (2), and 2-methoxy-5-nitronaphthalene (3) are reported.
Zusammenfassung
Es wird eine verbesserte Arbeitsvorschrift für einige isomere Methoxynitronaphthaline angegeben. Die Schlüsselverbindungen dazu sind die entsprechenden Nitronaphthylamine und Nitronaphthole. Es wird die Synthese von 1-Methoxy-3-nitronaphthalin (1), 1-Methoxy-5-nitronaphthalin (2) und 2-Methoxy-5-nitronaphthalin (3) beschrieben.
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References
Párkányi C., Lee Y. J. (1974) Tetrahedron Lett.: 1115
Jeffries A. T., Párkányi C. (1976) Z. Naturforsch.31 b: 345
Párkányi C. (1981) Bull. Soc. Chim. Belg.90: 599
Párkányi C. (1983) Pure Appl. Chem.55: 331
Párkányi C., Vernin G., Zamkotsian R. M., Metzger J. (1984) Heterocycles22: 1077
Gutiérrez A. R. (1971) M. S. Thesis (director: Párkányi C.). University of Texas at El Paso, El Paso, TX
Lee S. A. (1972) M. S. Thesis (director: Párkányi C.). University of Texas at El Paso, El Paso, TX
Párkányi C., Gutiérrez A. R., Lee Y. J., Lee S. A. (1972) Abstracts, 4th IUPAC Symposium on Photochemistry, Baden-Baden, Germany
Párkányi C., Gutiérrez A. R., Lee Y. J., Lee S. A. (1972) unpublished results
Letsinger R. L., Hautala R. R. (1969) Tetrahedron Lett.: 4205
Hautala R. R. (1970) Ph.D. Dissertation. Northwestern University, Evanston, IL
Beijersbergen van Henegouwen G. M. J. (1970) Ph.D. Dissertation. Rijksuniversiteit Leiden, Leiden, The Netherlands
Beijersbergen van Henegouwen G. M. J., Havinga E. (1970) Recl. Trav. Chim. Pays-Bas89: 907
Hautala R. R., Letsinger R. L. (1971) J. Org. Chem.36: 3762
Lammers J. G., de Gunst G. P., Havinga E. (1973) Recl. Trav. Chim. Pays-Bas92: 1386
Lammers J. G. (1974) Ph.D. Dissertation. Rijksuniversiteit Leiden, Leiden, The Netherlands
Taha-Bouamri K., Aaron J. J., Párkányi C., Sappok-Stang A., Boniface C. (1991) Abstracts, 15th International Conference on Photochemistry, Paris, France
Available from Aldrich Chemical Co., Milwaukee, WI
Available from Janssen Chimica, Beerse, Belgium
Available from TCI American Tokyo Kasei, Portland, OR
Fichter F., Kühnel T. (1909) Ber.42: 4748
Kaufler F., Brauer E. (1907) Ber.40: 3269
Hodgson H. H., Birtwell S. (1944) J. Chem. Soc.: 75
Veselý V., Rein E. (1929) Collect. Czech. Chem. Commun.1: 360
Hodgson H. H., Ward E. R. (1949) J. Chem. Soc.: 1187
Oelinek H. E., Zugravescu I. (1972) Rom. Pat. 49 844; (1973) C. A.79: 146173m
Rosenblatt D. H., Nachlas M. M., Seligman A. M. (1958) J. Am. Chem. Soc.80: 2463
Alger T. D., Grant D. M., Paul E. G. (1966) J. Am. Chem. Soc.88: 5397
Jones A. J., Alger T. D., Grant D. M., Litchman W. M. (1970) J. Am. Chem. Soc.92: 2386
Cohen A., Cook J. W., Hewett C. L., Girard A. (1934) J. Chem. Soc: 653
Hodgson H. H., Turner H. S. (1943) J. Chem. Soc.: 318
Vertalier S., Sannié C. (1954) Bull. Soc. Chim. Fr.: 234
Morrison D. C. (1962) J. Org. Chem.27: 296
Veselý V., Dvořák K. (1923) Bull. Soc. Chim. Fr. [4]33: 319
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Part of this work was carried out at the University of Texas at El Paso, El Paso, TX, during the tenure of one of the authors there (C.P.)
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Párkányi, C., Yuan, H.L., Sappok-Stang, A. et al. Improved synthesis of several methoxynitronaphthalenes. Monatsh Chem 123, 637–645 (1992). https://doi.org/10.1007/BF00816858
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DOI: https://doi.org/10.1007/BF00816858