Synthesis and reactions of 3-aroyl derivatives of 4-hydroxy-2-quinolones and 4-hydroxycoumarin

Journal of Heterocyclic Chemistry

Volumn 33, Issue 3, 1996, Pages 663-670

  Kappe, Thomas ^a   Schnell, Barbara ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

COUMARIN DERIVATIVE; PYRIDO[1,2 A]PYRIMIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINOLONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029764851     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570330324     Document Type: Article

References (33)

1. I. Iwataki, in Rational Approaches to Stucture, Activity, and Ecotoxicology of Agrochemicals, W. Draber and T. Fijita, ed, CRC Press, Boca Raton, 1992, pp 397-426.
2. M. W. James and K. G. Wayne, European Patent 90262, (1983); T Soeda and T. Uchida, Pestic. Biochem. Physiol., 29, 35 (1987).
3. M. W. James and K. G. Wayne, European Patent 90262, (1983); T Soeda and T. Uchida, Pestic. Biochem. Physiol., 29, 35 (1987).
4. Th. Kappe, R. Aigner, P. Hohengassner, and W. Stadibauer, J. Prakt. Chem., 336, 596 (1994); and literature cited therein.
5. P. Roschger and W. Stadibauer, Liebigs Ann. Chem., 821 (1990); P. Roschger, W. Fiala, and W. Stadibauer, J. Heterocyclic Chem., 29, 225 (1992).
6. P. Roschger and W. Stadibauer, Liebigs Ann. Chem., 821 (1990); P. Roschger, W. Fiala, and W. Stadibauer, J. Heterocyclic Chem., 29, 225 (1992).
7. J. Klosa, Arch. Pharm. (Weinheim), 288, 356 (1955); 289, 104 (1956).
8. J. Klosa, Arch. Pharm. (Weinheim), 288, 356 (1955); 289, 104 (1956).
9. E. Ziegler, G. Wildtgrube, and H. Junek, Monatsh. Chem., 87, 439 (1956).
10. J. E. Oliver, K. R. Wilzer, and R. M. Waters, Synthesis, 1117 (1990); and literature cited therein.
11. Though not strictly comparable, the rearrangement somewhat resembles the "anionic Fries rearrangement" of V. Snieckus [9].
12. M. P. Sibi and V. Snieckus, J. Org. Chem., 48, 1935 (1983); W. Wang and V. Snieckus, J. Org. Chem., 57, 424 (1992).
13. M. P. Sibi and V. Snieckus, J. Org. Chem., 48, 1935 (1983); W. Wang and V. Snieckus, J. Org. Chem., 57, 424 (1992).
14. Th. Kappe, R. Aigner, P. Roschger, B. Schnell, and W. Stadibauer, Tetrahedron, 51, 12923 (1995).
15. W. Stadlbauer, R. Laschober, H. Lutschounig, G. Schindler, and Th. Kappe, Monatsh. Chem., 123, 617 (1992); W. Stadlbauer, O. Schmut, and Th. Kappe, Monatsh. Chem., 111, 1005 (1980); P. Baumgarten and W. Kärgel, Chem. Ber., 60, 832 (1927).
16. W. Stadlbauer, R. Laschober, H. Lutschounig, G. Schindler, and Th. Kappe, Monatsh. Chem., 123, 617 (1992); W. Stadlbauer, O. Schmut, and Th. Kappe, Monatsh. Chem., 111, 1005 (1980); P. Baumgarten and W. Kärgel, Chem. Ber., 60, 832 (1927).
17. W. Stadlbauer, R. Laschober, H. Lutschounig, G. Schindler, and Th. Kappe, Monatsh. Chem., 123, 617 (1992); W. Stadlbauer, O. Schmut, and Th. Kappe, Monatsh. Chem., 111, 1005 (1980); P. Baumgarten and W. Kärgel, Chem. Ber., 60, 832 (1927).
18. Th. Kappe, R. Aigner, M. Jöbstl, P. Hohengassner, and W. Stadlbauer, Heterocyclic Commun., 1, 341 (1995).
19. W. Steinschifter, W. Fiala, and W. Stadibauer, J. Hetemcyclic Chem., 31, 1647 (1994); P. Roschger and W. Stadibauer, Liebigs Ann. Chem., 401 (1991); W. Fiala and W. Stadlbauer, J. Prakt. Chem., 335, 128 (1993).
20. W. Steinschifter, W. Fiala, and W. Stadibauer, J. Hetemcyclic Chem., 31, 1647 (1994); P. Roschger and W. Stadibauer, Liebigs Ann. Chem., 401 (1991); W. Fiala and W. Stadlbauer, J. Prakt. Chem., 335, 128 (1993).
21. W. Steinschifter, W. Fiala, and W. Stadibauer, J. Hetemcyclic Chem., 31, 1647 (1994); P. Roschger and W. Stadibauer, Liebigs Ann. Chem., 401 (1991); W. Fiala and W. Stadlbauer, J. Prakt. Chem., 335, 128 (1993).
22. O. A. Ponomarev, Yu. N. Brusil'tsev, V. K. H. Grif, and V. G. Mitina, Ukr. Khim. Zh., 56, 272 (1990).
23. A. E. Chichibabin, Chem. Ber., 57, 1168 (1924).
24. Th. Kappe, W. Lube, K. Thonhofer, C. Kratky, and U. G. Wagnex, Heterocycles, 40, 681 (1995).
25. A. R. Katritzky and A. J. Waring, J. Chem. Soc., 1544 (1962); A. R. Katritzky, F. D. Popp, and A. J. Waring, J. Chem. Soc. (B), 565 (1966).
26. A. R. Katritzky and A. J. Waring, J. Chem. Soc., 1544 (1962); A. R. Katritzky, F. D. Popp, and A. J. Waring, J. Chem. Soc. (B), 565 (1966).
27. Th. Kappe, P. F. Fritz, and E. Ziegler, Monatsh. Chem., 102, 412 (1971).
28. 1H spectra of all compounds listed in Tables 1-6 can be found in: B. Schnell, dissertation, University of Graz, 1994.
29. W. Friedrichsen, Th. Kappe, and A. Böttcher, Heterocycles, 19, 1083 (1982), review: see p 1099.
30. G. M. Coppola and G. E. Hardtmann, J. Heterocyclic Chem., 16, 1605 (1979).
31. E. Ziegler and H. Junek, Monatsh. Chem., 90, 762 (1959).
32. E. Ziegler, K. Belegratis and G. Brus, Monatsh. Chem., 98, 555 (1967).
33. This compound has been prepared previously by condensation of 3,4,5,6-tetrahydropicoline with diethylmalonate: J. Perronnet, A. Poittevin, L. Taliani (Roussel-UCLAF), French Demande 2,197,513; 29 March 1974; Chem. Abstr., 82, 112101h (1975), however no physical or analytical data are presented.