The first entry to pyrrolo[2,3-c]quinoline-2,4(3aH,5H)-diones

Tetrahedron

Volumn 64, Issue 19, 2008, Pages 4387-4402

  Kafka, Stanislav ^a   Klásek, Antonín ^a   Polis, Jiří ^a   Rosenbreierová, Veronika ^a   Palík, Ctibor ^a   Mrkvička, Vladimír ^a   Košmrlj, Janez ^b  

^a TOMAS BATA UNIVERSITY IN ZLIN   (Czech Republic)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Mechanism; NMR; Pyrrolo 2,3 c quinolones; Quinolinones; Wittig olefination

Indexed keywords

1 HYDROXY 1 PHENYL 1H PYRROLO[3,4 C]QUINOLINE 3,4(2H,5H) DIONE; 2 BROMO N (3 BUTYL 2,4 DIOXO 1,2,3,4 TETRAHYDROQUINOLINE 3 YL)ACETAMIDE; 2 BROMO N BUTYL N (3 BUTYL 2,4 DIOXO 1,2,3,4 TETRAHYDROQUINOLIN 3 YL)ACETAMIDE; 2 BUTYL 1 HYDROXY 1 PHENYL 1H PYRROLO[3,4 C]QUINOLINE 3,4(2H,5H) DIONE; 2 BUTYL 1 PHENYL 1H PYRROLO[3,4 C]QUINOLINE 3,4(2H,5H) DIONE; 3 AMINO 4 ETHOXYCARBONYLMETHYLENE 1,2,3,4 TETRAHYDRO 2 QUINOLONE DERIVATIVE; 3 AMINOQUINOLINE 2,4(1H,3H) DIONE DERIVATIVE; 3 BUTYL 3A METHYL 5 PHENYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H) DIONE; 3 BUTYL 3A PHENYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H) DIONE; 3 BUTYL 5 METHYL 3A PHENYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H) DIONE; 3,3A DIBUTYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H) DIONE; 3A BENZYL 3 BUTYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H) DIONE; 3A BENZYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H)DIONE; 3A BUTYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H) DIONE; 3A METHYL 5 PHENYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H) DIONE; 3A PHENYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H) DIONE; 4 BUTYL 3 PHENYL 3,4 DIHYDRO 1H BENZO[E][1,4]DIAZEPINE 2,5 DIONE; 5 METHYL 3A PHENYL 3,3A DIHYDRO 2H PYRROLO[2,3 C]QUINOLINE 2,4(5H) DIONE; ETHYL 2 (3 AMINO 1 METHYL 2 OXO 3 PHENYL 2,3 DIHYDROQUINOLIN 4(1H) YLIDENE)ACETIC ACID; ETHYL 2 (3 AMINO 2 OXO 3 PHENYL 2,3 DIHYDROQUINOLINE 4(1H) YLIDENE)ACETIC ACID; ETHYL 2 (3 AMINO 3 BENZYL 2 OXO 2,3 DIHYDROQUINOLIN 4(1H) YLIDENE)ACETIC ACID; ETHYL 2 (3 AMINO 3 BUTYL 2 OXO 2,3 DIHYDROQUINOLIN 4(1H) YLIDENE)ACETIC ACID; ETHYL 2 (3 AMINO 3 METHYL 2 OXO 1 PHENYL 2,3 DIHYDROQUINOLIN 4(1H) YLIDENE)ACETIC ACID; ETHYL 2 [3 (BUTYLAMINO) 1 METHYL 2 OXO 3 PHENYL 2,3 DIHYDROQUINOLIN 4(1H) YLIDENE]ACETIC ACID; ETHYL 2 [3 (BUTYLAMINO) 3 METHYL 2 OXO 1 PHENYL 2,3 DIHYDROQUINOLIN 4(1H) YLIDENE]ACETIC ACID; ETHYL 2 [3 BUTYL 3 (BUTYLAMINO) 2 OXO 2,3 DIHYDROQUINOLIN 4(1H) YLIDENE]ACETIC ACID; ETHYL 2 [BENZYL 3 (BUTYLAMINO) 2 OXO 3 PHENYL 2,3 DIHYDROQUINOLIN 4(1H) YLIDENE]ACETIC ACID; N (3 BENZYL 2,4 DIOXO 1,2,3,4 TETRAHYDROQUINOLIN 3 YL) 2 BROMOACETAMIDE; PYRROLO[2,3 C]QUINOLINE 2,4?(3AH,5H) DIONE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; OLEFINATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; THIN LAYER CHROMATOGRAPHY; TRANSAMINATION; WITTIG REACTION;

EID: 41549139959     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.063     Document Type: Article

References (35)

1. Klásek A., Kořistek K., Polis J., and Košmrlj J. Heterocycles 48 (1998) 2309-2326
2. Klásek A., Kořistek K., Polis J., and Košmrlj J. Tetrahedron 56 (2000) 1551-1560
3. Klásek A., Polis J., Mrkvička V., and Košmrlj J. J. Heterocycl. Chem. 39 (2002) 1315-1320
4. Klásek A., Kořistek K., Kafka S., and Košmrlj J. Heterocycles 60 (2003) 1811-1820
5. Klásek A., Mrkvička V., Pevec A., and Košmrlj J. J. Org. Chem. 69 (2004) 5646-5651
6. Košmrlj J., Kafka S., Leban I., and Grad M. Magn. Reson. Chem. 45 (2007) 700-704
7. Pomeisl K., Kvíčala J., Paleta O., Klásek A., Kafka S., Kubelka V., Havlíček J., and Čejka J. Tetrahedron 63 (2007) 10549-10561
8. Kafka S., Košmrlj J., Klásek A., and Pevec A. Tetrahedron Lett. 49 (2008) 90-93
9. Kafka S., Klásek A., Polis J., and Košmrlj J. Heterocycles 57 (2002) 1659-1682
10. Klásek A., Lyčka A., Holčapek M., and Hoza I. Tetrahedron 60 (2004) 9953-9961
11. Klásek A., Kořistek K., Lyčka A., and Holčapek M. Tetrahedron 59 (2003) 5279-5288
12. Klásek A., Lyčka A., Holčapek M., and Hoza I. J. Heterocycl. Chem. 43 (2006) 1251-1260
13. Kafka S., Kovář M., Klásek A., and Kappe T. J. Heterocycl. Chem. 33 (1996) 1977-1982
14. Klásek A., and Kafka S. J. Heterocycl. Chem. 35 (1998) 307-311
15. Beccalli E.M., Broggini G., Martinelli M., Paladino G., and Zoni C. Eur. J. Org. Chem. (2005) 2091-2096
16. Bergman J., and Rehn S. Tetrahedron 58 (2002) 9179-9185 and references cited therein
17. Fryer, I. R.; Ning, R. Y.-F.; Sternbach, L. H.; Walser, A. (Hoffmann-La Roche, Inc., USA) U.S. Patent 4,014,883, 1977;
18. Chem. Abstr. 87 (1977) 39450
19. Thal, C.; Boye, O.; Guenard, D.; Potier, P. (Centre National de la Recherche Scientifique, Fr.) Patent No. WO 9002733, 1990;
20. Chem. Abstr. 113 (1990) 115077
21. Alazard J.-P., Millet-Paillusson C., Guénard D., and Thal C. Bull. Soc. Chim. Fr. 133 (1996) 251-266
22. Gorlitzer K., Fabian J., Frohberg P., and Drutkowski G. Pharmazie 57 (2002) 243-247
23. Pfefferkorn, J. A.; Song, Y.; Trivedi, B. K. (Warner-Lambert Company LLC, USA), Patent No. WO 2006059210, 2006;
24. Chem. Abstr. 145 (2006) 45964
25. Nakahira, H.; Kimura, H.; Hochigai, H. (Dainippon Simitomo Pharma Co., Ltd, Japan) Patent No. WO 2006112331, 2006;
26. Chem. Abstr. 145 (2006) 454996
27. Bienayme, H.; Dumoulin, A.; Grisoni, S.; Kaloun, El B.; Poigny, S.; Rabot R.; Rahali, R.; Tam, E. (Pierre Fabre Medicament, Fr.) Patent No. FR 2887881, 2007;
28. Chem. Abstr. 146 (2007) 121944
29. It has been reported that bromoacetamides can be prepared from amines and bromoacetyl bromide in THF as a solvent, see, for example:
30. Suzuki T., Nagano Y., Matsuura A., Kohara A., Ninomiya S., Kohda K., and Miyata N. Bioorg. Med. Chem. Lett. 13 (2003) 4321-4326
31. Torres-Murro J., Quintero L., and Sartillo-Piscil F. Tetrahedron Lett. 46 (2005) 7691-7694
32. After our experiments in THF were completed, we came across with the work of Schneider and Viljoen who demonstrated how THF reacts with bromoacetyl bromide to afford 4-bromobutyl bromoacetate, see:. Schneider D.F., and Viljoen M.S. Synth. Commun. 32 (2002) 721-728
33. Bestmann H.J. Angew. Chem. 77 (1965) 609-613
34. Podesva C., Vagi K., and Solomon C. Can. J. Chem. 46 (1968) 2263-2269
35. Bonne D., Dekhane M., and Zhu J. Org. Lett. 7 (2005) 5285-5288