The synthesis of annulated azepin-3-one derivatives from 1,3,4-pentatrienyl nitrones by a heterocyclization - Rearrangement sequence

European Journal of Organic Chemistry

Volumn , Issue 17, 2001, Pages 3313-3332

  Knobloch, Karin ^a   Keller, Manfred ^a   Eberbach, Wolfgang ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

Alkynes; Allenes; Dihydroazepinones; Electrocyclic reactions; Nitrones

Indexed keywords

1,2 DIHYDRO[C]BENZAZEPIN 3 ONE DERIVATIVE; 1,3,4 PENTATRIENYL NITRONE; ALKYL GROUP; ALKYNE DERIVATIVE; ALLENE DERIVATIVE; AZEPIN 3 ONE; AZEPINE DERIVATIVE; CYCLOPROPANE DERIVATIVE; ISOINDOLE DERIVATIVE; NITRONE DERIVATIVE; POTASSIUM HYDROXIDE; THIOKETONE; UNCLASSIFIED DRUG; VINYL BROMIDE; VINYL DERIVATIVE;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; HYDROGENATION; ISOMERISM; REACTION ANALYSIS; SYNTHESIS;

EID: 0034849581     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200109)2001:17<3313::AID-EJOC3313>3.0.CO;2-E     Document Type: Article

References (69)

1. Reviews: [1a] 1,3-Dipolar Cycloaddition Chemistry, vol. 1 and 2 (Ed.: A. Padwa), John Wiley & Sons, New York, 1984.
2. [1b] V. A. Bakulev, C. O. Kappe, A. Padwa, Organic Synthesis: Theory and Applications 1996, vol. 3, p. 149-229.
3. Reviews: [2a] G. Zecchi, Synthesis 1991, 181-188.
4. [2b] P. W. Groundwater, M. Nyerges, Adv. Heterocycl. Chem. 1999, 73, 97-129.
5. [3a] W. Eberbach, J. Roser, Tetrahedron Lett. 1987, 28, 2689-2692.
6. [3b] W. Eberbach, W. Maier, Tetrahedron Lett. 1989, 30, 5591-5594.
7. [3c] W. Eberbach, N. Laber, Tetrahedron Lett. 1992, 31, 61-64.
8. H. U. Reißig, Nachr. Chem. Tech. Lab. 1986, 34, 237-240.
9. For instance, 5-exo-methylene isoxazolidines, formed by cycloaddition of nitrones to allenes, are transformed into 3-pyrrolidinones by initial N-O cleavage and subsequent N-C rebonding: A. Padwa, M. Matzinger, Y. Tomioka, M. K. Venkatramanan, J. Org. Chem. 1988, 53, 955-963.
10. [6a] J. Bussenius, N. Laber, T. Müller, W. Eberbach, Chem. Ber. 1994, 127, 247-259.
11. [6b] E. Lopez-Calle, J. Höfler, W. Eberbach, Liebigs Ann. 1996, 1855-1866.
12. D. J. Pasto, Tetrahedron 1984, 40, 2805-2827.
13. H. Hopf, in: The Chemistry of Allenes (Ed.: S. R. Landor), Academic Press, New York, 1982, vol. 2, p. 525-562.
14. [9a] W. Carruthers, in: Cycloaddition Reactions in Organic Synthesis, Pergamon Press, Oxford, Weinheim, 1990.
15. [9b] R. C. Larock, in: Comprehensive Organic Transformations, Wiley-VCH, 1999, p. 541.
16. [9c] U. Koop, G. Handke, N. Krause, Liebigs Ann. 1996, 1487-1499, and references.
17. For a recent review, see: G. Broggini, G. Zecchi, Gazz. Chim. Ital. 1996, 126, 479-488.
18. H. Hopf, in: The Chemistry of Allenes (Ed.: S. R. Landor), Academic Press, New York, 1982, vol. 2, p. 563-577.
19. K. Knobloch, Dissertation, Universität Freiburg, 2000.
20. For a preliminary communication, see: K. Knobloch, W. Eberbach, Org. Lett. 2000, 2, 1117-1120.
21. I. Z. Egenburg, Russ. Chem. Rev. 1978, 47, 470-485.
22. [15a] S. Nagashima, K. Kanematsu, Tetrahedron: Asymmetry 1990, 1, 743-749.
23. [15b] J. D. Spence, J. K. Wyatt, D. M. Bender, D. K. Moss, M. H. Nantz, J. Org. Chem. 1996, 61, 4014-4021.
24. [15c] T. Choshi, T. Sada, H. Fujimoto, C. Nagayama, E. Sugino, S. Hibino, J. Org. Chem. 1997, 62, 2535-2543.
25. [15d] M. Oku, S. Arai, K. Katayama, T. Shioiri, Synlett 2000, 493-494.
26. The ring transformation of type 7 → 8 can be brought about either by thermal or by photochemical activation of 4-isoxazolines: [16a] P. Grünanger, P. Vita-Finzi, in: Heterocyclic Compounds (Ed.: J. E. Dowling), Wiley, New York, 1999, vol. 49, part 2, p. 575f and 696f.
27. [16b] E. Lopez-Calle, W. Eberbach, J. Chem. Soc., Chem. Commun. 1994, 301-302.
28. The crystallographic data (excluding structure factors) have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-160786 (9a) and -160787 (31a). Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
29. [18a] W. Eberbach, J. Roser, Tetrahedron 1986, 42, 2221-2234.
30. [18b] W. Maier, W. Eberbach, Helv. Chim. Acta 1991, 74, 1095-1101.
31. - K. Marx, W. Eberbach, Chem. Eur. J. 2000, 6, 2063-2068.
32. [18c] Y. Tan, T. Hartmann, V. Huch, H. Dürr, P. Valat, V. Wintgens, J. Kossanyi, J. Org. Chem. 2001, 66, 1130-1137.
33. Reviews on cyclopropanones: [19a] N. J. Turro, Acc. Chem. Res. 1969, 2, 25-32.
34. [19b] H. H. Wasserman, G. M. Clark, P. C. Turley, Top. Curr. Chem. 1974, 47, 73-156.
35. For a recent review on isoindoles, see: T. J. Donohoe, in: Science of Synthesis, Houben-Weyl Methods of Molecular Transformations (Ed.: E. J. Thomas), Thieme, Stuttgart, 2000, vol. 10, p. 653-692.
36. The structural assignment of the vinyl bromide 9′p by spectroscopic data was unambiguously confirmed by comparison with the independently prepared 9p (see below).
37. [22a] J. C. Looker, J. Org. Chem. 1972, 37, 1059-1060.
38. [22b] A. Roedig, H.-A. Renk, V. Schaal, P. Schentzow, Chem. Ber. 1974, 107, 1136-1146.
39. [22c] M. J. van Eis, B. S. E. van der Linde, F. J. J. de Kanter, W. H. Wolf, F. Bickelhaupt, J. Org. Chem. 2000, 65, 4348-4354.
40. 10 are known: [23a] P. Duhamel, M. Kotera, J. Chem. Res. (M) 1982, 2851-2862.
41. [23b] E. C. Taylor, J. E. Dowling, Bioorg. Med. Chem. Lett. 1997, 7, 453-456.
42. [23c] M. W. Read, M. L. Miller, P. S. Ray, Tetrahedron 1999, 55, 373-392.
43. [24a] P. Wipf, Y. Kim, D. M. Goldstein, J. Am. Chem. Soc. 1995, 111, 11106-11112.
44. [24b] T. Polonski, M. J. Milewska, A. Konitz, M. Gdaniec, Tetrahedron: Asymmetry 1999, 10, 2591-2604.
45. For similar bromodesylilations of α-pyridone derivatives, see: [25a] R. A. Earl, K. P. C. Vollhardt, J. Org. Chem. 1984, 49, 4786-4800.
46. [25b] E. Lopez-Calle, Diplomarbeit, Universität Freiburg, 1992.
47. [25c] J. Höfler, Dissertation, Universität Freiburg, 2000.
48. [26a] W. M. Bright, H. A. Lloyd, J. V. Silverton, J. Org. Chem. 1976, 41, 2454-2458.
49. [26b] H. Wagner, J. Burghart, Helv. Chim. Acta 1981, 64, 283-296.
50. [26c] C. Seguineau, P. Richomme, J. Bruneton, Helv. Chim. Acta 1992, 75, 2283-296.
51. [27a] J. O. Hawthorne, L. E. Mihelic, U. S. Patent 3,668,232, 1972; Chem. Abstr. 1972, 77, P101199s; U. S. Patent 3,551,414, 1970;
52. Chem. Abstr. 1971, 74, P125484v.
53. [27b] V. K. Gorshkova, A. S. Saratikov, L. G. Tignibidina, Pharm. Chem. J. (Engl. Transl. ) 1994, 28, 158-162.
54. [27c] P. J. Voorstad, J. M. Chapman, G. H. Cocolas, S. D. Wyrick, I. H. Hall, J. Med. Chem. 1985, 28, 9-12.
55. J. Rigaudy, C. Igier, J. Barcelo, Tetrahedron Lett. 1975, 16, 3845-3848.
56. K. Knobloch, W. Eberbach, in preparation.
57. J. L. Charlton, M. M. Alauddin, J. Org. Chem. 1986, 51, 3490-3493.
58. W. Eberbach, in: Methoden Org. Chem. (Houben-Weyl), 4 ed., 1994, vol. E6a, part 1, p. 141.
59. M. E. Jung, J. A. Hagenah, J. Org. Chem. 1987, 52, 1889-1902.
60. T. Nicola, Dissertation, Universität Freiburg, 2001.
61. D. E. Bogucki, J. L. Charlton, J. Org. Chem. 1995, 60, 588-593.
62. F. Taherirastgar, L. Brandsma, Synth. Commun. 1997, 27, 4035-4040.
63. T. Nishikawa, S. Shibuya, S. Hosokawa, M. Isobe, Synlett 1994, 485-486.
64. [37a] B. Majoie, Ger. Offen. 2030625, 1969.
65. [37b] S. Gronowitz, U. Michael, Ark. For. Kemi 1970, 32, 283-294.
66. [37c] M. - C. Zaluski, M. Robba, M. Bonhomme, Bull. Soc. Chem. Fr. 1970, 1838-1846.
67. [37d] K. Knobloch, Diplomarbeit, Universität Freiburg, 1995.
68. T. L. Gilchrist, R. J. Summersell, J. Chem. Soc., Perkin Trans. 1 1988, 2595-2601.
69. W. M. Owton, M. Brunavs, Synth. Commun. 1991, 21, 981-987.