Regioselective three-component synthesis of novel indeno[1,2-b]-pyrazolo[4, 3-e]pyridines-fused derivatives of 4-azafluorenone alkaloid

Journal of Heterocyclic Chemistry

Volumn 45, Issue 1, 2008, Pages 155-159

  Quiroga, Jairo ^a   Cobo, Débora ^a   Insuasty, Braulio ^a   Abonía, Rodrigo ^a   Cruz, Silvia ^b   Nogueras, Manuel ^c   Cobo, Justo ^c  

^a UNIVERSIDAD DEL VALLE   (Colombia)

^b UNIVERSIDAD DE NARIÑO   (Colombia)

^c UNIVERSITY OF JAÉN   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

4 AZAFLUORENONE; 5 AMINOPYRAZOL; ALKALOID DERIVATIVE; BENZALDEHYDE DERIVATIVE; INDENE DERIVATIVE; INDENO[1,2 B]PYRAZOLO[4,3 E]PYRIDINE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; COMPLEX FORMATION; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; POLYMERIZATION; REACTION ANALYSIS;

EID: 38949175028     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570450116     Document Type: Article

References (33)

1. Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
2. Orru, R.V.A.; de Greef, M. Synthesis 2003, 1471.
3. Domling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
4. Nair, V.; Rajesh, C.; Vinod, A.V.; Bindu, S.; Sreekanth, A.R.; Mathen, J.S.; Balagopal, L. Acc. Chem. Res. 2003, 36, 899.
5. Zhu, Eur. J. Org. Chem. 2003, 7, 1133.
6. Domling, A. Curr. Opin. Chem. Biol. 2002, 6, 306.
7. Strunz, G.M.; Findlay, J.A. The Alkaloids, Vol. 26; Academic Press, New York, NY, 1985, pp 89.
8. de Almeida, M.E.I.; Braz, F.R.; von Bulow, M.V.; Gottleib, O.R.; Maia, J.G.S. Phytochemistry, 1976, 15, 1186.
9. Padwa, A.; Heidelbaugh, T.M.; Kuethe, J.T. J. Org. Chem. 2000, 65, 2368.
10. Heintzelman, G.R.; Averill, K.M.; Dodd, J.H.; Demarest, K.T.; Tang, Y.; Jackson, P.F. WO 2003088963 A1, 2002; Chem. Abstr. 2003, 139, 350637.
11. Heintzelman, G.R.; Averill, K.M.; Dodd, J.H.; Demarest, K.T.; Tang, Y.; Jackson, P.F. U.S. Patent US 2004082578, 2003; Chem. Abstr. 2004, 140, 375085.
12. Safak, C.; Simsek, R.; Altas, Y.; Boydag, S.; Erol, K. Boll. Chim. Farm. 1997, 136, 665.
13. Rentzea, C.; Meyer, N.; Kast, J.; Plath, P.; Koenig, H.; Harreus, A.; Kardorff, U.; Gerber, M.; Walter, H. German Patent DE 4301426 A1, 1993. Chem. Abstr. 1994, 121, 133986.
14. Prostakov, N.S.; Vasil'ev, G.A.; Zvolinski, V.P.; Varlamov, A.V.; Savina, A.A.; Sorokin, O.I.; Lopatina, N.D. Chem. Heterocycl. Compd. (N.Y.), 1975, 971.
15. Prostakov, N.S.; Soldatenkov, A.T.; Radzhan, P.K.; Fedorov, V.D.; Fomichev, A.A.; Rezakov, V.A. Chem. Heterocycl. Compd. (N.Y.), 1982, 390.
16. Tadic, D.; Cassels, B.K.; Cavé, A.; Goulart, M.P.F.; de Oliveira, A.B. Phytochemistry 1987, 26, 1551.
17. Alves, T.; de Oliveira, A.B. Snieckus, V. Tetrahedron Lett. 1988, 29, 2135.
18. Tadic, D.; Cassels, B.K.; Cavé, A. Heterocycles 1988, 27, 407.
19. Koyama, J.; Okatani, T.; Tagahara, K. Heterocycles 1989, 29, 1648.
20. Emelen, K.V.; Wit, T.D.; Hoornaert, G.J.; Compemolle, F. Tetrahedron 2002, 58, 4225.
21. Elmaati, T.M.; Said, S.B.; Elenein, N.S.A.; Khodeir, N.M.; Sofan, M.M. J. Heterocyclic Chem. 2003, 40, 481.
22. Zhang, J.; El-Shabrawy, O.; El-Shabrawy, M.A.; Jr. Schiff, P.L.; Slatkin, D.J. J. Nat. Prod. 1987, 50, 800.
23. Nitta, M.; Ohnuma, M.; Lino, Y. J. Chem. Soc., Perkin Trans. 1 1991, 1115.
24. Quiroga, J.; Portilla, J.; Serrano, H.; Abonía, R.; Insuasty, B.; Nogueras, M.; Cobo, J. Tetrahedron Lett. 2007, 48, 1987.
25. Quiroga, J.; Cisneros, C.; Insuasty, B.; Abonía, R.; Nogueras, M.; Sortino, M.; Zacchino, S. J. Heterocyclic Chem. 2006, 43, 463.
26. Quiroga, J.; Cruz, S.; Insuasty, B.; Abonía, R.; Nogueras, M.; Cobo, J. Tetrahedron Lett. 2006, 47, 27.
27. Quiroga, J.; Portilla, J.; Insuasty, B.; Abonía, R.; Nogueras, M.; Sortino, M.; Zacchino, S. J. Heterocyclic Chem., 2005, 42, 61.
28. Tu, S.J.; Miao, C.B.; Gao, Y.; Fang, F.; Zhuang, Q.Y.; Feng, Y.J.; Shi, D.Q. Synlett. 2004, 255.
29. Tu, S.J.; Jiang, B.; Jia, R.H.; Zhang, J.Y.; Zhang, Y.; Yao, C.S.; Shi, F. Org. Biomol. Chem. 2006, 4, 3664.
30. Tu, S.J.; Jiang, B.; Zhang, J.Y.; Jia, R.H.; Zhang, Y.; Yao, C.S. Org. Biomol. Chem. 2006, 4, 3980.
31. Tu, S.; Jiang, B.; Jia, R.; Zhang, J.; Zhang, Y. Tetrahedron Lett. 2007, 48, 1369.
32. Low, J.N.; Cobo, J.; Cisneros, C.; Quiroga, J.; Glidewel, C. Acta Cryst. 2004, C60, 186.
33. Cobo, D.; Quiroga, J.; Cobo, J.; Low, J.N.; Glidewell, C. Acta Cryst. 2006, E62, 5176.