Hetero Diels-Alder reactions of 1-acetylamino- and 1-dimethylamino-1- azadienes with benzoquinones

Tetrahedron

Volumn 56, Issue 11, 2000, Pages 1561-1567

  Pérez, José María ^a   López Alvarado, Pilar ^a   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

Benzoquinones; Diels Alder reactions; Quinolines; Quinones

Indexed keywords

ALKADIENE; ANTHRAQUINONE DERIVATIVE; BENZOQUINONE DERIVATIVE; DIMETHYLAMINE; HETEROCYCLIC COMPOUND; QUINOLINE DERIVATIVE; QUINONE DERIVATIVE;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; HEATING; ISOMERISM; OXIDATION; PRIORITY JOURNAL;

EID: 0343503001     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00058-2     Document Type: Article

References (31)

1. Lown J.W. Chem. Soc. Rev. 22:1993;165.
2. Sengupta S.K. Foye W.O., Cancer Chemotherapeutic Agents. 1995;American Chemical Society, New York. (Chapter 5).
3. Abe N., Enoki N., Nakakita Y., Uchida H., Nakamura T., Munekata M. J. Antibiot. 46:1993;1536. (and references therein).
4. Nakatani K., Okamoto A., Matsuno T., Saito I. J. Am. Chem. Soc. 120:1998;11 219.
5. Konishi M., Ohkuma H., Tsuno T., Oki T., Van Duyne G.D., Clardy J. J. Am. Chem. Soc. 112:1990;3715.
6. Nicolau K.C., Dai W.-M., Hong Y.P., Tsay S.-C., Baldridge K.K., Siegel J.S. J. Am. Chem. Soc. 115:1993;7944.
7. Krapcho A.P., Maresch M.J., Hacker M.P., Hazelhurst L., Menta E., Oliva A., Spinelli S., Beggiolin G., Giuliani F.G., Pezzoni G., Tognella S. Current Med. Chem. 2:1995;803.
8. Villacampa M., de la Cuesta E., Avendaño C. Tetrahedron. 51:1995;1259.
9. Potts K.T., Walsh E.B., Bhattacharjee D. J. Org. Chem. 52:1987;2285.
10. Tapia R.A., Quintanar C., Valderrama J.A. Heterocycles. 43:1996;447.
11. Tietze L.F., Kettschau G. Top. Curr. Chem. 189:1997;1.
12. Barluenga J., Tomás M. Adv. Heterocycl. Chem. 57:1993;1.
13. Blanco M.M., de la Fuente J.A., Avendaño C., Menéndez J.C. Tetrahedron Lett. 40:1999;4097.
14. Pérez J.M., Avendaño C., Menéndez J.C. Tetrahedron. 51:1995;6573.
15. Villacampa M., Pérez J.M., Avendaño C., Menéndez J.C. Tetrahedron. 50:1994;10047.
16. Waldner A. Helv. Chim. Acta. 71:1988;486.
17. Wichelhaus H. Chem. Ber. 1879;1500.
18. Hegedus L.S., Sestrick M.R., Michaelson E.T., Harrington P.J. J. Org. Chem. 54:1989;4141.
19. Nebois P., Fillion H. Tetrahedron Lett. 32:1991;1307.
20. Nebois P., Fillion H., Benameur L. Tetrahedron. 49:1993;9767.
21. Echavarren A.M. J. Org. Chem. 55:1990;4255.
22. Valderrama J.A., González M.F. Heterocycles. 36:1993;1553.
23. Blanco M.M., Alonso M.A., Avendaño C., Menéndez J.C. Tetrahedron. 52:1996;5933.
24. Ramos M.T., Díaz-Guerra L.-M., García-Copín S., Avendaño C., García-Grávalos D., García de Quesada T. Il Farmaco. 51:1996;375.
25. Perumal P.T., Bhat M.V. Synthesis. 1979;205.
26. For the synthesis of the azadienes 5, 8, 9, 11 and 12, see Ref. 16. Methacrolein dimethylhydrazone 10 was prepared using similar conditions (see also Ref. 14). Acrolein dimethylhydrazone 8 was prepared according to: Gómez-Bengoa, E.; Echavarren, A. M. J. Org. Chem. 1991, 56, 3497.
27. For the preliminary report of the double hetero Diels-Alder reaction between 1-dimethylamino-1-azadienes and 2,6-dibromobenzoquinone, see: Pérez, J. M.; Avendaño, C.; Menéndez, J. C. Tetrahedron Lett. 1997, 26, 4717.
28. We have noticed a similar effect in the Diels-Alder reactions of 2,5,8(1H)-quinolinetriones. See Refs. 14 and 23.
29. Nebois P., Barrett R., Fillion H. Tetrahedron Lett. 31:1990;2569.
30. Similar conditions have been employed for the synthesis of chloroquinolinequinones from 1-dimethylamino-1-azedienes and the less reactive dichlorobenzoquinones. See: Lévesque, S.; Brassard, P. Heterocycles 1994, 38, 2205.
31. Braude. J. Chem. Soc. 1945;490.