Selective and efficient transformation of 5,6,7,8-tetrahydro-2H-1-benzopyran-2,5-diones with hydrazines to 5-hydrazono-2H-1-benzopyran-2-ones and quinoline-2,5-diones. Extension to related systems

Tetrahedron

Volumn 53, Issue 4, 1997, Pages 1383-1390

  Trebše, Polonca ^a   Polanc, Slovenko ^a   Kočevar, Marijan ^a   Šolmajer, Tomaž ^b   Grdadolnik, Simona Golič ^b  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOPYRAN DERIVATIVE; QUINOLINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031037684     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01050-2     Document Type: Article

References (36)

1. (a) Hepworth, J. D. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon Press: Oxford, 1984, Vol. 3, pp. 737-883.
2. (b) Ellis, G. P. In ref. 1a, Vol. 3, pp. 647-736.
3. (a) Thaisrivongs, S.; Watenpaugh, K. D.; Howe, W. J.; Tomich, P. K.; Dolak, L. A.; Chong, K.-T.; Tomich, C.-S. C.; Tomasselli, A. G.; Turner, S. R.; Strohbach, J. W.; Mulichak, A. M.; Janakiraman, M. N.; Moon, J. B.; Lynn, J. C.; Horng, M.-M.; Hinshaw, R. R.; Curry, K. A.; Rothrock, D. J. J. Med. Chem. 1995, 38, 3624-3637.
4. (b) Prasad, J. V. N. V.; Lunney, E. A.; Ferguson, D.; Tummino, P. J.; Rubin, J. R.; Reyner, E. L.; Stewart, B. H.; Guttendorf, R. J.; Domagala, J. M.; Suvorov, L. I.; Gulnik, S. V.; Topol, I. A.; Bhat, T. N.; Erickson, J. W. J. Am. Chem. Soc. 1995, 117, 11070-11074.
5. (c) Shen, L. L.; Mitscher, L. A.; Sharma, P. N.; O'Donnell, T. J.; Chu, D. W. T.; Cooper, C. S.; Rosen, T.; Pernet, A. G. Biochemistry 1989, 28, 3886-3894.
6. (d) Lewis, R. J.; Singh, O. M. P.; Smith, C. V.; Skarzynski, T.; Maxwell, A.; Wonacott, A. J.; Wigley, D. B. EMBO J. 1996, 15, 1412-1420.
7. (e) Longobardi, M.; Bargagna, A.; Mariani, E.; Schenone, P.; D'Amico, M.; Filippelli, A.; Falzarano, C.; Lampa, E. Farmaco 1993, 48, 1121-1130.
8. (f) Mosti, L.; Menozzi, G.; Schenone, P.; D'Amico, M.; Falciani, M.; Rossi, F. Farmaco 1994, 49, 45-50.
9. (a) Jones, G. In ref. 1a, Vol. 2, pp. 395-510.
10. (b) Roedig, A.; Hilberth, J.; Renk, H. A. Liebigs Ann. Chem. 1975, 2251-2260.
11. (c) Kvita, V. Synthesis 1991, 883-884.
12. (d) Elguero, J. In ref. 1a, Vol. 5, pp. 167-343.
13. (e) Ram, V. J.; Verma, M.; Hussaini, F. A., Shoeb, A. Liebigs Ann. Chem. 1991, 1229-1231.
14. (f) Rachedi, Y.; Hamdi, M.; Sakellariou, R.; Spéziale, V. Synth. Commun. 1991, 21, 1189-1199.
15. (a) Oehldrich, J.; Cook, J. M. J. Org. Chem. 1977, 42, 889-894.
16. (b) Chang, J. C.; El-Sheikh, M.; Harmon, A.; Avasthi, K.; Cook, J. M. J. Org. Chem. 1981, 46, 4188-4193.
17. (c) Kočevar, M.; Polanc, S.; Tišler, M.; Verček, B. Heterocycles 1990, 30, 227-230.
18. (d) Fink, D. M.; Bores, G. M.; Effland, R. C.; Huger, F. P.; Kurys, B. E.; Rush, D. K.; Selk, D. E. J. Med. Chem. 1995, 38, 3645-3651.
19. (e) Trebše, P.; Polanc, S.; Kočevar, M.; Šolmajer, T. Heterocycles 1996, 43, 809-816.
20. (a) Clark, J. S. In Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Pergamon: Oxford, 1995, Vol. 3, pp. 443-490.
21. (b) Bergbreiter, D. E.; Momongan, M. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, 1991, Vol. 2, pp. 503-526.
22. (c) Sucrow, W. Org. Prep. Proced. Int. 1982, 14, 93-155.
23. (d) Fusco, R.; Sannicolo, F. Tetrahedron 1980, 36, 161-170.
24. (a) Kočevar, M.; Polanc, S.; Tišler, M.; Verček, B. Synth. Commun. 1989, 19, 1713-1719.
25. (b) Kepe, V.; Kočevar, M.; Polanc, S.; Verček, B.; Tišler, M. Tetrahedron 1990, 46, 2081-2088.
26. Dayagi, S.; Degani, Y. In The Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Interscience: London, 1970; pp. 61-147.
27. Roth, H. J.; Langer, G. Arch. Pharm. 1968, 301, 810-817.
28. (a) Krueger, P. J. In The Chemistry of the Hydrazo, Azo and Azoxy Groups; Patai, S., Ed.; Interscience: London, 1975; pp. 153-224.
29. (b) Karabatsos, G. J.; Taller, R. A. J. Am. Chem. Soc. 1963, 85, 3624-3629.
30. (a) Spartan®, Spartan Version 4.0, Wavefunction, Inc., Von Karman, 210, Irvine, CA 92715 USA.
31. (b) Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909.
32. (a) Takahayashi, N. J. Pharm. Soc. Japan 1955, 75, 778-781; Chem. Abstr. 1956, 50, 4970c.
33. (a) Takahayashi, N. J. Pharm. Soc. Japan 1955, 75, 778-781; Chem. Abstr. 1956, 50, 4970c.
34. (b) Stanovnik, B.; Tišler, M. Tetrahedron 1967, 23, 387-395.
35. (c) Takahayashi, N. J. Pharm. Soc. Japan 1956, 76, 765-767; Chem. Abstr. 1957, 51, 1192d.
36. (c) Takahayashi, N. J. Pharm. Soc. Japan 1956, 76, 765-767; Chem. Abstr. 1957, 51, 1192d.