Synthesis of chromeno[2,3-b]carbazole and chromeno[3,2-f]indazole derivatives. A new class of indole- and pyrazole-fused polycyclic compounds using o-quinodimethane chemistry. A reactivity and regioselectivity computational study

Arkivoc

Volumn 2008, Issue 14, 2008, Pages 132-157

  Terzidis, Michalis A ^a   Tsoleridis, Constantinos A ^a   Stephanidou Stephanatou, Julia ^a  

^a Department of Chemistry   (Greece)

Author keywords

Carbazoles; Chromones; Diels Alder reactions; Indazoles; o quinodimethanes; Pyrazoles

Indexed keywords

EID: 54949089015     PISSN: 1551-7012     EISSN: 15517012     Source Type: Journal    
DOI: 10.3998/ark.5550190.0009.e15     Document Type: Article

References (48)

1. (a) Dewick, P. M. In The Flavonoids: Advances in Research Since 1986; Harborne, J. B., Ed.; Chapmann & Hall: New York, 1994; p 23.
2. nd Ed., Blackie: Surrey, 1993; p 60.
3. (c) Manthy, J. A.; Buslig, B. S.; Eds.; In Flavonoids in the Living Systems: Advances in Experimental Medicine and Biology; Plenum: New York, 1998; Vol. 439.
4. (c) Levai A. Arkivoc 2004, 15.
5. (d) Silva, A. M. S.; Pinto, D. C. G. A.; Cavaleiro, J. A. S.; Levai, A.; Patonay, T. Arkivoc 2004, 106.
6. (a) Korkina, G. L.; Alafan'ev, I. B. Advances in Pharmacology; Sies, H., Ed.; Academic: San Diego, 1997; Vol. 38, p.151.
7. (b) Hansch, C.; Sammes, P. G.; Taylor, J. B., Edt.; Comprehensive Medicinal Chemistry; Pergamon: London 1990; Vol. 6.
8. (a) Ghosh, C. K.; Ghosh, C. Indian J. Chem. 1997, 36B, 968.
9. (b) Hsung, R. P. J. Org. Chem. 1997, 62, 7904.
10. (c) Valenti, P.; Bisi, A.; Rampa, A.; Belluti, F.; Gobbi, S.; Zampiron, A.; Carrara, M. Bioorg. Med. Chem. 2000, 8, 239.
11. (d) Malhotra, S.; Shakya, G.; Kumar, A.; Vanhoecke, B. W.; Cholli, A. L.; Raj, H.G.; Saso, L.; Ghosh, B.; Bracke, M. E.; Prasad, A. K.; Biswal, S.; Parmar, V. S. ARKIVOC 2008, (vi), 119.
12. (e) Singh, G.; Singh, R.; Girdhar, N. K.; Ishar, M. P. S. Tetrahedron 2002, 58, 2471.
13. (a) Kumar, S. K. J. Med. Chem. 2003, 46, 2813;
14. (b) Wang, Y. Q.; Bioorg. Med. Chem. 2003, 11, 1569;
15. (c) Gao, Y.; Li, D. J.; Keung, W. M. Bioorg. Med. Chem. 2003, 11, 4069;
16. (d) Ishar, M. P. S.; Singh, G.; Singh, S.; Sreenivasan K. K.; Singh G. Bioorg. Med. Chem. Lett. 2006, 16, 1366.
17. For a review on the biological activities and synthesis of chromone derivatives see: Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev. 2003, 103, 893.
18. (a) Martínez-Grau, A.; Marco, J. L. Bioorg. Med. Chem.Lett. 1997, 24, 3165.
19. (b) Mohr, S. J.; Chirigos, M. A.; Fuhrman, F. S.; Pryor, J. W. Cancer Res. 1975, 35, 3750.
20. (c) El-Agrody, A. M.; El-Hakim, M. H.; Abd El-Latif, M. S.; Fakery, A. H.; El-Sayed E. S. M.; El-Ghareab, K. A. Acta Pharm. 2000, 50, 111.
21. (a) Ghosh, C. K. J. Heterocycl. Chem. 1983, 20, 1437;
22. (b) Ghosh, C. K. Indian J. Chem. 1997, 36B, 968;
23. (c) Ghosh, C. K. Heterocycles 2004, 63, 2875.
24. (a) Sabitha, G. Aldrichim. Acta 1996, 29, p 5 and references cited therein.
25. (b) Ghosh, C.; Tewari, N. J. Org. Chem. 1980, 45, 1964.
26. (a) Kona, J.; Fabian, W. M. F.; Zahradnik, P. J. Chem. Soc., Perkin Trans. 2 2001, 422.
27. (b) Kona, J.; Zahradnik, P.; Fabian, W. M. F. J. Org. Chem. 2001, 66, 4998.
28. Borrell, J. I.; Teixido, J.; Schuler, E.; Michelotti, E. Tetrahedron Lett. 2001, 42, 5331. 11.
29. (a) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Tetrahedron 2002, 56, 105.
30. (b) Sandulache, A.; Silva, A. M. S.; Cavaleiro, J. A. S. Monatsch. Chem. 2003, 134, 551.
31. (c) Cremins, P. J.; Saengchantara, S. T.; Wallace, T. W. Tetrahedron 1987, 43, 3075.
32. (a) Pozarentzi, M.; Stephanidou-Stephanatou, J.; Tsoleridis, C. A. Tetrahedron Lett. 2003, 44, 2007.
33. (b) Neochoritis, C.; Livadiotou, D.; Stephanidou-Stephanatou, J.; Tsoleridis C. A. Tetrahedron Lett. 2007, 48, 2275.
34. (c) Neochoritis, C.; Stephanidou-Stephanatou, J.; Tsoleridis C. A. Synlett. 2007, 16, 2596.
35. Terzidis, M.; Tsoleridis, C. A.; Stephanidou-Stephanatou J. Tetrahedron Lett. 2005, 46, 7239.
36. (a) Saroya, B.; Srinivasan, P.C. Tetrahedron Lett. 1984, 25, 5429.
37. (b) Pindur, U.; Gonzalez, E.; Mehrabani, F. J. Chem. Soc., Perkin Trans. I 1997, 1861.
38. Mitkidou, S.; Stephanidou-Stephanatou, J. Tetrahedron Lett. 1990, 31, 5197.
39. Terzidis, M.; Tsoleridis, C. A.; Stephanidou-Stephanatou J. Tetrahedron 2007, 63, 7828.
40. For most compounds the spin system of the saturated protons as well as of the aromatic protons has also been studied by simulation (SpinWorks ver. 2.5).
41. McIver Jr., J. W.; Komornicki, A. J. Am. Chem. Soc. 1972, 94, 2625.
42. Di Valentin, C.; Freccero, M.; Sarzi-Amadè, Zanalettti, R. Tetrahedron 2000, 56, 2547.
43. (a) Nohara, A.; Sugihara, H.; Ukawa, K. Jpn Patent; Chem. Abstr. 1986, 104, 186390.
44. (b) Nohara, A.; Sugihara, H.; Ukawa, K. Jpn Patent; Chem. Abstr. 1986, 104, 207250.
45. MOPAC 2000 ver. 1.11, Fujitsu.
46. 1H nmr are presented, due to the overlapping. Carbon chemial shifts of the minor isomers were assigned by estimation acccordingly to the major isomers.
47. 2.
48. 1H nmr.