Coupling reactions of 1,2-bis(2-indolyl)ethane. Formation of indolo[2,3-c]carbazoles

Heterocyclic Communications

Volumn 3, Issue 5, 1997, Pages 397-400

  Bergman, Jan ^c   Desarbre, Eric ^c   Janosik, Tomasz ^c   Lidgren, Göran ^a   Venemalm, Lennart ^b  

^a Swedish Pharmaucetical Society   (Sweden)

^b PFIZER INC   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0031315857     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.1997.3.5.397     Document Type: Article

References (22)

1. Gillner, M.; Bergman, J.; Cambillau, C.; Fernström, B.; Gustafsson, J.-Å. Mol. Pharmacol. 1985, 28, 357-363.
2. Gillner, M.; Bergman, J.; Cambillau, C.; Alexandersson, M.; Fernström, B.; Gustafsson, J.-Å. Mol. Pharmacol. 1993, 44, 336-345.
3. Chen, Y.-H.; Riby, J.; Srivastava, P.; Bartholomew, J.; Denison, M.; Bjeldanes, L. J. Biol. Chem. 1995, 270, 22548-22555.
4. Kleman, M. I.; Poellinger, L.; Gustafsson, J.-Å. J. Biol. Chem. 1994, 269, 5137-5144.
5. Rannug, U.; Rannug, A.; Sjöberg, U.; Li, H.; Westerholm, R.; Bergman, J. Chem. & Biol. 1995, 2, 841-845.
6. Katritzky, A. R.; Li, J.; Stevens, C. V. J. Org. Chem. 1995, 60, 3401-3404, and references cited therein.
7. Robinson, B. J. Chem. Soc. 1963, 3097-3099.
8. Weller, H.; Grellman, K.-H. J. Am. Chem. Soc. 1983, 105, 6268-6273.
9. 11b by Clifton and Plant as early as 1951. However, the structure has never been confirmed.
10. Clifton, P. V.; Plant, S. G. P. J. Chem. Soc. 1951, 461-466.
11. Katritzky, A. R.; Akutagawa, K. Tetrahedron Lett. 1985, 26, 5935-5938.
12. 6) δ 27.3 (t), 98.2 (d), 110.5 (d), 118.5 (d), 119.1 (d), 120.0 (d), 128.2 (s), 135.9 (s), 139.3 (s) ppm. MS m/z (relative intensity) 260 (72), 130 (100). Mp>260 °C.
13. Lavilla, R.; Gotsens, T.; Rodriguez, S.; Bosch, J. Tetrahedron 1992, 48, 6445-6454.
14. 6) δ 25.3 (t), 109.6 (s), 110.2 (d), 118.4 (d), 120.2 (d), 122.6 (d), 128.8 (s), 134.3 (S), 136.7 (s) ppm.
15. Bergman, J.; Carlsson, R.; Misztal, S. Acta Chem. Scand. 1976, 853-862.
16. McKillop, A.; Turrell, A. G.; Young, D. W.; Taylor, E. C. J. Am. Chem. Soc. 1980, 102, 6504-6512.
17. 3-group is undetectable due to very slow relaxation. MS m/z (relative intensity) 340 (46), 271 (100), Mp>260 °C.
18. 3-group and the adjacent carbon as well. MS m/z (relative intensity) 336 (100). Mp>260 °C.
19. Cosmo, R.; Sternhell, S. Aust. J. Chem. 1987, 40, 35-47.
20. 6) δ 27.5 (q), 31.4 (t), 37.9 (s), 111.2 (d), 118.2 (d), 119.0 (s), 120.1 (d), 121.4 (d), 128.0 (s), 134.4 (s), 135.6 (s) ppm.
21. Bergman, J.; Norrby, P.-O.; Tilstam, U.; Venemalm, L. Tetrahedron 1989, 45, 5549-5564.
22. Fischer, E. Ber. 1886, 19, 2988-2992.