Synthesis of sulfur-containing tricyclic ring systems by means of photoinduced decarboxylative cyclizations

European Journal of Organic Chemistry

Volumn , Issue 10, 2001, Pages 1831-1843

  Griesbeck, Axel G ^a   Oelgemöller, Michael ^a,b   Lex, Johann ^a   Haeuseler, Andreas ^c   Schmittel, Michael ^c  

^a UNIVERSITY OF COLOGNE   (Germany)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c UNIVERSITY OF SIEGEN   (Germany)

Author keywords

Cyclic voltammetry; Cyclizations; Decarboxylations; Electron transfer; Photochemistry; Phthalimides; Thioethers

Indexed keywords

3 (METHYLSULFANYL)PROPIONIC ACID; CARBOXYLIC ACID DERIVATIVE; MERCAPTOPROPIONIC ACID; PHTHALIMIDE DERIVATIVE; PROPIONIC ACID DERIVATIVE; SULFUR; THIOGLYCOLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DECARBOXYLATION; ELECTRON TRANSPORT; IRRADIATION; QUANTUM MECHANICS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035025608     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200105)2001:10<1831::AID-EJOC1831>3.0.CO;2-7     Document Type: Article

References (68)

1. [1a] A. G. Griesbeck, Chimia 1998, 52, 272.
2. [1b] A. G. Griesbeck, Liebigs Ann. 1996, 1951.
3. [2a] Y. Kanaoka, Acc. Chem. Res. 1978, 87, 407.
4. [2b] Y. Kanaoka, J. Soc. Org. Synth. Chem. (Tokyo) 1975, 33, 949.
5. [2c] J. D. Coyle in Synthetic Organic Photochemistry (Ed.: W. M. Horspool), Plenum Press, New York, 1984, p. 259.
6. [2d] P. H. Mazzocchi, Org. Photochem. 1981, 5, 421.
7. [2e] A. G. Griesbeck, H. Mauder in CRC Handbook of Organic Photochemistry and Photobiology (Eds.: W. M. Horspool, P.-S. Song), CRC Press, Boca Raton, 1995, p. 513.
8. [3a] A. G. Griesbeck, W. Kramer, M. Oelgemöller, Synlett 1999, 1169.
9. [3b] A. G. Griesbeck, A. Henz, W. Kramer, J. Lex, F. Nerowski, M. Oelgemöller, K. Peters, E.-M. Peters, Helv. Chim. Acta 1997, 80, 912.
10. [4a] A. G. Griesbeck, J. Hirt, W. Kramer, P. Dallakian, Tetrahedron 1998, 54, 3169.
11. [4b] A. G. Griesbeck, J. Hirt, K. Peters, E.-M. Peters, H. G. von Schnering, Chem. Eur. J. 1996, 2, 1388.
12. [5a] Y. Hatanaka, Y. Sato, H. Nakai, M. Wada, T. Mizoguchi, Y. Kanaoka, Liebigs Ann. Chem. 1992, 1113.
13. [5b] Y. Sato, H. Nakai, M. Wada, T. Mizoguchi, Y. Hatanaka, Y. Migita, Y. Kanaoka, Liebigs Ann. Chem. 1985, 1099.
14. N. J. Pienta in Photoinduced Electron Transfer (Ed.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, p. 421.
15. L. Eberson in Electron Transfer Reactions in Organic Chemistry ("Reactivity and Structure - Concepts in Organic Chemistry", V. 25) (Ed.: K. Hafner), Springer-Verlag, Berlin, 1987.
16. T. O. Soine, M. R. Buchdahl, Org. Synth. 1967, 106.
17. M. B. Winstead, H. W. Heine, J. Am. Chem. Soc. 1955, 77, 1913.
18. Y.-D. Gong, N. Iwasawa, Chem. Lett. 1994, 2139.
19. G. H. L. Nefkens, Nature (London) 1962, 193, 974.
20. J. Loccufier, E. Schacht, Bull. Soc. Chim. Belg. 1988, 97, 535.
21. [13a] J. C. Sheehan, M. Goodman, G. P. Hess, J. Am. Chem. Soc. 1956, 78, 1367.
22. [13b] J. C. Sheehan, D. W. Chapman, R. W. Roth, J. Am. Chem. Soc, 1952, 74, 3822.
23. The geometries were pre-optimized using a MM+ force field. PM3, as implemented in the Hyperchem software package, was used for further optimizations. Hyperchem Molecular Modeling System, Version 4 for Windows, Hypercube Inc. 1994.
24. H. Görner, A. G. Griesbeck, T. Heinrich, W. Kramer, M. Oelgemöller, Chem. Eur. J., in print.
25. [16a] U. C. Yoon, S. J. Lee, K. J. Lee, S. J. Cho, C. W. Lee, P. S. Mariano, Bull. Korean Chem. Soc. 1994, 15, 154.
26. [16b] U. C. Yoon, H. J. Kim, P. S. Mariano, Heterocycles 1989, 29, 1041.
27. T. Ikeno, M. Harada, N. Arai, K. Narasaka, Chem. Lett. 1997, 169.
28. [18a] Z. Su, P. S. Mariano, D. E. Falvey, U. C. Yoon, S. W. Oh, J. Am. Chem. Soc. 1998, 120, 10676.
29. [18b] Z. Su, D. E. Falvey, U. C. Yoon, P. S. Mariano, J. Am. Chem. Soc. 1997, 119, 5261.
30. [19a] D. R. G. Brimage, R. S. Davidson, P. R. Steiner, J. Chem. Soc., Perkin 1 1973, 526.
31. [19b] R. S. Davidson, P. R. Steiner, J. Chem. Soc., Perkin 2 1972, 1357.
32. [19c] R. S. Davidson, P. R. Steiner, J. Chem. Soc. C 1971, 1682.
33. I. R. Gould, S. Farid, Acc. Chem. Res. 1996, 29, 522.
34. [21a] A. G. Griesbeck, M. Oelgemöller, Synlett 1999, 492.
35. [21b] A. G. Griesbeck, M. Oelgemöller, J. Lex, Synlett 2000, 1454.
36. A. G. Griesbeck, M. Oelgemöller, Synlett 2000, 71.
37. [23a] H. De Koning, W. N. Speckamp, Methods of Organic Chemistry (Houben-Weyl) 1995, 21b, 1953.
38. [23b] H. Hiemstra, W. N. Speckamp in Comprehensive Organic Synthesis, vol. 2 (Ed.: C. H. Heathcock), Pergamon Press, Oxford, 1991, p. 1047.
39. A. G. Griesbeck, F. Nerowski, J. Lex, J. Org. Chem. 1999, 64, 5213.
40. H. Yokoi, T. Nakano, W. Fujita, K. Ishiguro, Y. Sawaki, J. Am. Chem. Soc. 1998, 120, 12453.
41. A. G. Griesbeck, W. Kramer, M. Oelgemöller, Green Chem. 1999, 1, 205.
42. [27a] H. J. Roth, G. Hundeshagen, Arch. Pharm. 1976, 309, 58.
43. [27b] M. Machida, H. Takechi, Y. Shishido, Y. Kanaoka, Synthesis 1982, 1078.
44. U. C. Yoon, S. W. Oh, S. M. Lee, S. J. Cho, J. Gamlin, P. S. Mariano, J. Org. Chem. 1999, 64, 4411.
45. H. Görner, A. G. Griesbeck, M. Oelgemöller, unpublished results.
46. [30a] P. J. Wagner, Acc. Chem. Res. 1983, 16, 461.
47. [30b] H. Jiang, H. Xu, J. Ye, J. Chem. Soc., Perkin Trans. 2 2000, 925.
48. [31a] Y. Ge T. Ouimet, D. K. Smith, J. Org. Chem. 2000, 65, 8831.
49. [31b] N. Gupta, H. Linschitz, J. Am. Chem. Soc. 1997, 119, 6384.
50. [31c] J. Carr, L. Lambert, D. E. Hibbs, M. B. Hursthouse, K. M. Abdul Malik, J. H. R. Tucker, Chem. Commun. 1997, 1649.
51. [32a] Y. Sato, H. Nakai, T. Mizoguchi, M. Kawanishi, Y. Hatanaka, Y. Kanaoka, Chem. Pharm. Bull. 1982, 30, 1263.
52. [32b] Y. Sato, H. Nakai, T. Mizoguchi, M. Kawanishi, Y. Hatanaka, Y. Kanaoka, Chem. Pharm. Bull. 1973, 21, 1164.
53. While wave III in Figure 6 appears only partly reversible, the reversibility is further increased in multisweep experiments.
54. K. Soai, A. Ookawa, J. Chem. Sac., Perkin Trans. 1 1986, 759.
55. A. Haeuseler, M. Schmittel, A. G. Griesbeck, M. Oelgemöller, unpublished results.
56. J. M. Savéant, E. Vianello, Electrochim. Acta 1967, 12, 1545.
57. E. Larsson, Ber. Dtsch. Chem. Ges. 1930, 63, 1347.
58. H. Schindlbauer, Monatsh. Chem. 1973, 104, 848.
59. [39a] M. Donike, Chromatographia 1976, 9, 440.
60. [39b] M. Donike, J. Chromatogr. 1975, 115, 591.
61. [39c] M. Donike, R. Gola, L. Jaenicke, J. Chromatogr. 1977, 134, 385.
62. M. Schmittel, A. Burghart, H. Werner, M. Laubender, R. Söllner, J. Org. Chem. 1999, 64, 3077.
63. C. Amatore, C. Lefrou, F. Pflügler, J. Electroanal. Chem. Interfacial 1989, 270, 43.
64. R. S. Nicholson, Anal. Chem. 1966, 1406.
65. K. Peters, E.-M. Peters, A. G. Griesbeck, M. Oelgemöller, Z. Kristall. NCS 1998, 213, 757.
66. K. Peters, E.-M. Peters, M. Oelgemöller, J.-M. Cho, A. G. Griesbeck, Z. Kristall. NCS 2000, 215, 37.
67. [24]
68. α radiation (λ = 0.71073 Å), graphite monochromator, -ω scans, 2 Θ limits [°]: 2-54. Structure analysis and refinement: solved by direct methods; full-matrix, least-squares refinement with anisotropic thermal parameters for C, N, and O and isotropic parameters for H. Programs used: SHELXS-97 for structure determination and SHELXL-97for refinement. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-156985 (trans-4), -156984 (3h), -156986 (7a), and -156987 (12),. Copies of the data can be obtained free of charge from CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/336-033, E-mail: deposit@ccdc.cam.ac.uk].