New Diels-Alder reactions of 3-vinylindoles with an aryne: Selective access to functionalized [a]anellated carbazoles

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 14, 1996, Pages 1767-1771

  Gonzalez, Eugenia ^a   Pindur, Ulf ^a   Schollmeyer, Dieter ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748895857     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19960001767     Document Type: Article

References (36)

1. G. W. Gribble, The Ellipticine Alkaloids in The Alkaloids, ed. A. Brossi, Academic Press, New York, London, 1990, vol. 39, pp. 239-343.
2. D. P. Chakraborty and S. Roy, Fortschr. Chem. Org. Naturst., eds. W. Herz, G. W. Kirby, W. Steglich and C. Tamm, 1991, 57, 71.
3. J. Bergman, Stereoselective Synthesis, Part A in Studies in Natural Products Chemistry, ed. Atta-ur-Rhaman, Elsevier, Amsterdam, 1988, vol. 1, p. 8.
4. U. Kuckländer, H. Pitzler and K. Kuna, Arch. Pharm. (Weinheim, Ger.), 1994, 327, 137.
5. A. Segall, H. Pappa, R. Causabon, G. Martin, R. Bergoc and M. T. Pizzorno, Eur. J. Med. Chem., 1995, 30, 165.
6. U. Pindur, M. Haber and K. Sattler, J. Chem. Educ., 1993, 70, 263.
7. P. Juret, A. Tanguy, A. Girard, J. Y. Le Talaer, J. S. Abbatucci, N. Dat-Xuong, J.-B. Le Pecq and C. Paoletti, Eur. J. Cancer, 1978, 14, 205.
8. N. Ph. Buu-Hoi, N. Hoan and N. H. Khoi, J. Org. Chem., 1949, 14, 492.
9. E. von Angerer and J. Prekajac, J. Med. Chem., 1986, 29, 380.
10. G. W. Gribble, M. G. Saulnier, M. P. Sibi and J. A. Obaza-Nutaitis, J. Org. Chem., 1984, 49, 4518.
11. (a) M. G. Saulnier and G. W. Gribble, Tetrahedron Lett., 1983, 5435;
12. (b) G. W. Gribble, D. J. Keavy, D. A. Davis, M. G. Saulnier, B. Pelcman, T. C. Barden, M. R. Sibi, E. R. Olson and J. J. Belbruno, J. Org. Chem., 1992, 57, 5878;
13. for a review see G. W. Gribble, Synlett, 1991, 269.
14. C. J. Moody, Synlett, 1994, 681.
15. A. R. Katritzky and L. Xie, J. Org. Chem., 1995, 60, 3707.
16. R. W. Hoffmann, Dehydrobenzene and cycloalkynes, Verlag Chemie, Weinheim, Academic Press, New York, 1967.
17. H. G. Reinecke, Tetrahedron, 1982, 38, 427;
18. H. G. Reinecke, E. S. Brown, B. P. Capehart, D. E. Minter and R. K. Freeman, Tetrahedron, 1988, 44, 5675.
19. S. Brooks, M. Sainsbury and D. K. Weerasinge, Tetrahedron, 1982, 38, 3019.
20. U. Pindur, Cycloaddition Reactions of Indole Derivatives in Advances in Nitrogen Heterocycles, ed. C. J. Moody, JAI Press, Greenwich 1995, vol. 1, pp. 121-172.
21. M. J. S. Dewar, E. G. Zoebisch, E. F. Healy and J. J. P. Stewart, J. Am. Chem. Soc., 1985, 107, 3902;
22. J. J. P. Stewart, J. Comput. Chem., 1989, 10, 209. AMI calculation details of the compounds. The 3-vinylindoles were calculated in the s-cis conformation and full geometry optimization was achieved: 3: E(HOMO) = -8.33 eV; HOMO coefficients at C(2′) = -0.3725, C(1′) = -0.3523, C(3) = 0.4036, C(2) = 0.4704; nett atomic charge at C(2′) = -0.03, C(1′) = -0.17, C(3) = -0.06, C(2) = -0.06. 4: E(HOMO) = -8.64 eV; HOMO coefficients at C(2′) = -0.3663, C(1′) = -0.2188, C(3) = 0.3811, C(2) = 0.3868; nett atomic charge at C(2′) = -0.22, C(1′) = -0.04, C(3) = -0.07, C(2) = -0.05, 5: E(HOMO) = -8.10 eV; HOMO coefficients at C(2′) = -0.2586, C(1′) = -0.1503, C(3) = 0.4799, C(2) = 0.3373; nett atomic charge at C(2′) = -0.22, C(1′) = 0.00, C(3) = -0.11, C(2) = -0.06. 6: E(HOMO) = -8.39 eV; HOMO coefficients at C(2′) = -0.3863, C(1′)= -0.1331, C(3) = 0.4920, C(2) = 0.3277; nett atomic charge at C(2′) = -0.23, C(1′) = 0.02, C(3) = -0.15, C(2) = -0.02. Aryne: E(LUMO) = -0.69 eV; LUMO coefficients (py) at C(1) = 0.5231, C(2) = -0.5222; nett atomic charge at C(1) = -0.12, C(2) = -0.12. 3,4-pyridyne: E(LUMO) = -1.15 eV; LUMO coefficients (py) at C(3) = 0.4501, C(4) = -0.1418; nett atomic charge at C(3) = -0.16, C(4) = -0.09.
23. U. Pindur, M.-H. Kim, M. Rogge, W. Massa and M. Molinier, J. Org. Chem., 1992, 57, 910.
24. L. Pfeuffer and U. Pindur, Helv. Chim. Acta, 1987, 70, 1419.
25. L. Pfeuffer and U. Pindur, Helv. Chim. Acta, 1988, 71, 467;
26. L. Pfeuffer, Ph.D. Thesis, University of Mainz, 1986.
27. L. Friedman and F. M. Logullo, J. Org. Chem., 1969, 84, 3089;
28. F. M. Logullo, A. M. Seitz and L. Friedman, Org. Synth., 1973, 5, 54.
29. C. May and C. J. Moody, Tetrahedron Lett., 1985, 26, 2123.
30. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 1976, 734.
31. (a) R. A. Jones in Comprehensive Heterocyclic Chemistry, eds. C. W. Bird and G. W. H. Cheeseman, Pergamon Press, Oxford 1984, vol. 4, p. 280;
32. (b) X. Zhang, S. I. Khan and C. S. Foote, J. Org. Chem., 1993, 58, 7839.
33. S. Osmund de Silva and V. Snieckus, Can. J. Chem., 1973, 52, 1294.
34. 1H-coupling constants on the basis of MMX force field calculations was used: C. A. G. Haasnot, F. A. A. M. De Leeuw and C. Altona, Tetrahedron, 1980, 36, 2783. The X ray coordinates of 11 were used as input geometry for the molecular mechanics calculations. Starting directly from the MMX building module gave similar geometrical results.
35. A. Altomare, M. C. Burla, M. Camalli, G. Cascarano, C. Giacovazzo, A. Guagliardi and G. Polidori, J. Appl. Crystallogr., Part 3, 1994, 27, 435.
36. G. M. Sheldrick, SHELXL-93. Program for Crystal Structure Refinement, University of Göttingen, Germany, 1993.