A new entry to the substituted pyrrolo[3,2-c]quinoline derivatives of biological interest by intramolecular heteroannulation of internal imines

Tetrahedron

Volumn 60, Issue 28, 2004, Pages 5873-5880

  Testa, Maria Luisa ^a   Lamartina, Liliana ^b   Mingoia, Francesco ^a  

^a CNR   (Italy)

^b UNIVERSITY OF PALERMO   (Italy)

Author keywords

Internal imines, NMR chemical shifts; Intramolecular heteroannulation; Pyrrolo 3,2 c quinoline derivatives

Indexed keywords

1 (2 AMINOPHENYL) 2 (2,5,7 TRIMETHYLPYRAZOLO[1,5 A]PYRIMIDIN 6 YL) 1 ETHANONE; 1 (2 NITROPHENYL) 2 (2,5,7 TRIMETHYLPYRAZOLO[1,5 A]PYRIMIDIN 6 YL) 1 ETHANONE; 2 ACETYL 3 METHYL 5 PHENYL 5,6 DIHYDROPYRROLO[1,2 C]QUINOZOLINE; 3 ACETYL 1 ETHYL 2 METHYL 4 DIPHENYL 1H PYRROLO[3,2 C]QUINOLINE; 3 ACETYL 1 ETHYL 2 METHYL 5 (2 NITROPHENYL) 1H PYRROLE; 3 ACETYL 1,2 DIMETHYL 4 DIPHENYL 1H PYRROLO[3,2 C]QUINOLINE; 3 ACETYL 1,2 DIMETHYL 5 (2 NITROPHENYL) 1H PYRROLE; 3 ACETYL 2 METHYL 1,4 DIPHENYL 1H PYRROLO[3,2 C]QUINOLINE; 3 ACETYL 2 METHYL 4 (5 METHYLFURAN 2 YL) 1 PHENYL 1H PYRROLO[3,2 C]QUINOLINE; 3 ACETYL 2 METHYL 4 DIPHENYL 1H PYRROLO[3,2 C]QUINOLINE; 3 ACETYL 2 METHYL 5 (2 NITROPHENYL) 1 PHENYL 1H PYRROLE; 3 ACETYL 2 METHYL 5 (2 NITROPHENYL) 1H PYRROLE; 3 ACETYL 5 (2 AMINOPHENYL) 1 ETHYL 2 METHYL 1H PYRROLE; 3 ACETYL 5 (2 AMINOPHENYL) 1,2 DIMETHYL 1H PYRROLE; 3 ACETYL 5 (2 AMINOPHENYL) 2 METHYL 1 PHENYL 1H PYRROLE; 3 ACETYL 5 (2 AMINOPHENYL) 2 METHYL 1H PYRROLE; 3 ETHYL ESTER 2 METHYL 1,4 DIPHENYL 1H PYRROLO[3,2 C]QUINOLINE; 5 (2 AMINOPHENYL) 3 ETHYL ESTER 2 METHYL 1 PHENYL 1H PYRROLE; AMINE; PYRROLE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; MOLECULAR BIOLOGY; OXIDATION; PRIORITY JOURNAL;

EID: 2942708002     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.047     Document Type: Article

References (44)

1. Khan M.A., Fereira da Rocha J. J. Heterocycl. Chem. 15:1978;913-921
2. Kang S.K., Park S.S., Kim S.S., Choi J.K., Yum E.K. Tetrahedron Lett. 40:1999;4379-4382
3. Witherup K.M., Ransom R.W., Graham A.C., Bernard A.M., Salvatore M.J., Lumma W.C., Anderson P.S., Piztenberger S.M., Varga S.L. J. Am. Chem. Soc. 117:1995;6682-6685
4. Khan M.A., Fereira da Rocha J. Heterocycles. 12:1979;857-872
5. Dudouit F., Houssin R., Hénichart J.P. J. Heterocycl. Chem. 38:2001;755-758
6. Helissey, Parrot-Lopez H., Renault J., Cros S. Eur. J. Med. Chem. 22:1987;366-368
7. Helissey P., Giorgi-Renault S., Parrot-Lopez H., Renault J., Cros S. Chem. Pharm. Bull. 37:1989;2413-2416
8. Helissey P., Cros S., Giorgi-Renault S. Anticancer Drug Des. 9:1994;51-67
9. Brown T.H., Ife R.J., Keeling D.J., Laing S.M., Leach C.A., Parsons M.E., Price C.A., Reavill D.R., Wiggall K.J. J. Med. Chem. 33:1990;527-533
10. Escolano C., Jones K. Tetrahedron Lett. 41:2000;8951-8955
11. Wright G.C., Watson E.J., Ebetino F.F., Lougheed G., Stevenson B.F., Winterstein A., Bickerton R.K., Halliday R.P., Pals D.T. J. Med. Chem. 14:1971;1060-1066
12. (b) Shonafinger, K.; Ong, H. U. (Hoechst-Roussel Pharmaceuticals, Inc., USA). Eur. Pat. Appl., 1988, CAN 110:38974 AN 1989:38974.
13. Skonicki, J. S.; Kearney, R. M. US 5, 216, 162, and references cited therein.
14. Lovely J.C., Mahmud H. Tetrahedron Lett. 40:1999;2079-2082
15. Helissey P., Parrot-Lopez H., Renault J., Cros S. Chem. Pharm. Bull. 35:1987;3547-3557
16. Gurjar M.K., Pal S., Rama Rao A.V. Heterocycles. 45:1997;231-234
17. Babu G., Perumal P.T. Tetrahedron. 54:1998;1627-1638
18. Escolano C., Jones K. Tetrahedron. 58:2002;1453-1464
19. Mingoia F. Tetrahedron. 57:2001;10147-10153
20. Mingoia F., Diana P., Barraja P., Lauria A., Almerico A.M. Heterocycles. 53:2000;1975-1985
21. Almerico A.M., Mingoia F., Diana P., Barraja P., Montalbano A., Lauria A., Loddo R., Sanna L., Delpiano D., Setzu M.G., Musiu C. Eur. J. Med. Chem. 37:2002;3-10
22. Passannanti A., Diana P., Mingoia F., Barraja P., Lauria A., Cirrincione G. J. Heterocycl. Chem. 35:1998;1535-1537
23. Passannanti A., Diana P., Barraja P., Mingoia F., Lauria A., Cirrincione G. Heterocycles. 48:1998;1229-1235
24. Aiello E., Dattolo G., Cirrincione G., Plescia S., Daidone G. J. Heterocycl. Chem. 16:1979;209-211
25. Aiello E. Atti Accad. Sci. Lett., Arti Palermo. 30:1970;237-241. CA: 1972, Vol. 77, 152110p
26. Scindo H., Fujishita T., Sasatani T., Chomei N., Takada S. Heterocycles. 29:1989;899-912
27. Khan M.A., Fereira da Rocha J. J. Heterocycl. Chem. 15:1978;913-921
28. Kang S.K., Park S.S., Kim S.S., Choi J.K., Yum E.K. Tetrahedron Lett. 40:1999;4379-4382
29. Dudouit F., Houssin R., Hénichart J.P. J. Heterocycl. Chem. 38:2001;755-758
30. Brown T.H., Ife R.J., Keeling D.J., Laing S.M., Leach C.A., Parsons M.E., Price C.A., Reavill D.R., Wiggall K.J. J. Med. Chem. 33:1990;527-533
31. Helissey P., Parrot-Lopez H., Renault J., Cros S. Chem. Pharm. Bull. 35:1987;3547-3557
32. Mekheimer R.A. Synthesis. 14:2000;2078-2084
33. Rodriguez A.L., Koradin C., Dohle W., Knochel P. Angew. Chem., Int. Ed. 39:2000;2078-2084
34. (g) JPN. Kokai Tokkyo Koho 2001, 203, 855, 28 August, 2001.
35. Burns G.D., Coe P.L., Andrews C.L. J. Chem. Soc., Perkin Trans. 1. 2001;552-557
36. Görlitzer K., Heinrici C. Pharmazie. 53:1998;847-853
37. Leach C.A., Brown T.H., Ife R.J., Keeling D.J., Laing S.M., Parsons M.E., Price C.A., Reavill D.R., Wiggall K.J. J. Med. Chem. 35:1992;1845-1852
38. Aiello E., Dattolo G., Cirrincione G., Almerico A.M., D'Asdia I. J. Heterocycl. Chem. 18:1981;1153-1155
39. Aiello E., Dattolo G., Cirrincione G. J. Chem. Soc., Perkin Trans. 1. 1981;1-3
40. Dattolo G., Cirrincione G., Almerico A., D'Asdia I., Aiello E. Heterocycles. 19:1982;681-686
41. Dattolo G., Cirrincione G., Aiello E. J. Heterocycl. Chem. 17:1980;701-703
42. Adams H., Anderson J.C., Cubbon R., James D.S., Mathias J.P. J. Org. Chem. 64:1999;8256-8262
43. Cox E.D., Cook J.M. Chem. Rev. 95:1995;1797-1842
44. Aliphatic aldehydes will be considered in further studies