Azirine/oxindole ring enlargement via amidinium intermediates

Helvetica Chimica Acta

Volumn 87, Issue 9, 2004, Pages 2385-2404

  Mekhael, Maged K G ^a,b   Bienz, Stefan ^a   Linden, Anthony ^a   Heimgartner, Heinz ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b GENETIC ENGINEERING AND BIOTECHNOLOGY RESEARCH INSTITUTE   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; FLUORINE COMPOUNDS; HYDRATES; HYDROCHLORIC ACID; SEPARATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

OXINDOLES; RING ENLARGEMENT;

AMINES;

2 AMINO 3H INDOLINIUM TETRAFLUOROBORATE DERIVATIVE; 2 DIHYDROINDOL 2 IMINE DERIVATIVE; 2,3 DIHYDROINDOL 2 ONE DERIVATIVE; 2H AZIRIN 3 AMINE; ACETIC ANHYDRIDE; AMIDINE; AZIRINE DERIVATIVE; BORON TRIFLUORIDE; BORON TRIFLUORIDE DIETHYL ETHERATE; DICHLOROMETHANE; HYDROCHLORIC ACID; INDOLE DERIVATIVE; INDOLIUM HYDROXIDE; OXINDOLE; SODIUM HYDROXIDE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL REACTION; CHROMATOGRAPHY; CRYSTAL STRUCTURE; EXTRACTION; HYDROLYSIS; PRIORITY JOURNAL; SYNTHESIS;

EID: 5644302935     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/hlca.200490216     Document Type: Article

References (58)

1. R. J. Sundberg, 'Indoles', Academic Press, New York, 1996, p. 5.
2. B. Robinson, 'The Fischer Indole Synthesis', John Wiley, Chichester, 1982.
3. G. Baccolini, P. E. Todesco, J. Chem. Soc., Chem. Commun. 1981, 563.
4. M. Nakazaki, K. Yamamoto, J. Org. Chem. 1976, 41, 1877.
5. P. G. Gassman, T. J. van Bergen, D. P. Gilbert, B. W. Cue, J. Am. Chem. Soc. 1974, 96, 5495.
6. D. H. Lloyd, D. E. Nichols, Tetrahedron Lett. 1983, 24, 4561; W. Haefliger, H. Knecht, Tetrahedron Lett. 1984, 25, 285.
7. D. H. Lloyd, D. E. Nichols, Tetrahedron Lett. 1983, 24, 4561; W. Haefliger, H. Knecht, Tetrahedron Lett. 1984, 25, 285.
8. W. J. Houlihan, V. A. Parrino, Y. Uike, J. Org. Chem. 1981, 46, 4511.
9. M. K. G. Mekhael, R. J. Smith, S. Bienz, A. Linden, H. Heimgartner, Z. Naturforsch., B 2002, 57, 444.
10. M. K. G. Mekhael, H. Heimgartner, Helv. Chim. Acta 2003, 86, 2805.
11. M. Rens, L. Ghosez, Tetrahedron Lett. 1970, 3765; cf. L. Ghosez, J. Marchand-Brynaert, in 'Iminium Salts in Organic Chemistry', Eds. H. Böhme, H. G. Viehe, John Wiley & Sons, New York, 1976, p. 421; L. Ghosez, in 'Medicinal Chemistry V', Ed. J. Mathieu, Elsevier, Amsterdam, 1977, p. 363.
12. M. Rens, L. Ghosez, Tetrahedron Lett. 1970, 3765; cf. L. Ghosez, J. Marchand-Brynaert, in 'Iminium Salts in Organic Chemistry', Eds. H. Böhme, H. G. Viehe, John Wiley & Sons, New York, 1976, p. 421; L. Ghosez, in 'Medicinal Chemistry V', Ed. J. Mathieu, Elsevier, Amsterdam, 1977, p. 363.
13. M. Rens, L. Ghosez, Tetrahedron Lett. 1970, 3765; cf. L. Ghosez, J. Marchand-Brynaert, in 'Iminium Salts in Organic Chemistry', Eds. H. Böhme, H. G. Viehe, John Wiley & Sons, New York, 1976, p. 421; L. Ghosez, in 'Medicinal Chemistry V', Ed. J. Mathieu, Elsevier, Amsterdam, 1977, p. 363.
14. H. Heimgartner, Angew. Chem., Int. Ed. 1991, 30, 238.
15. B. P. Chandrasekhar, U. Schmid, R. Schmid, H. Heimgartner, H. Schmid, Helv. Chim. Acta 1975, 58, 1191.
16. C. Bernard-Henriet, P. Hoet, L. Ghosez, R. Touillaux, Tetrahedron Lett. 1981, 22, 4717.
17. P. Vittorelli, H. Heimgartner, H. Schmid, P. Hoet, L. Ghosez, Tetrahedron 1974, 30, 3737.
18. P. Wipf, H. Heimgartner, Helv. Chim. Acta 1990, 73, 13.
19. R. Luykx, C. B. Bucher, A. Linden, H. Heimgartner, Helv. Chim. Acta 1996, 79, 527.
20. K. N. Koch, A. Linden, H. Heimgartner, Tetrahedron 2001, 57, 2311.
21. T. R. Mihova, A. Linden, H. Heimgartner, Helv. Chim. Acta 1996, 79, 2067.
22. B. Hostettler, J.-P. Obrecht, R. Prewo, J. H. Bieri, H. Heimgartner, Helv. Chim. Acta 1986, 69, 298.
23. A. Rahm, A. Linden, B. R. Vincent, H. Heimgartner, M. Mühlstädt, B. Schulze, Helv. Chim. Acta 1991, 74, 1002.
24. A. S. Orahovats, A. Linden, H. Heimgartner, Helv. Chim. Acta 1992, 75, 2515.
25. A. S. Orahovats, S. S. Bratovanov, A. Linden, H. Heimgartner, Helv. Chim. Acta 1996, 79, 1121.
26. T. R. Mihova, A. Linden, H. Heimgartner, Heterocycles 1998, 49, 215.
27. M. Schläpfer-Dähler, H. Heimgartner, Helv. Chim. Acta 1993, 76, 2398.
28. F. Arnhold, S. Chaloupka, A. Linden, H. Heimgartner, Helv. Chim. Acta 1995, 78, 899.
29. P. Hoet, 'Etude de la Réactivité des Amino-2 Azirines-1', Ph.D. thesis, Université Catholique de Louvain, 1975.
30. M. Hugener, H. Heimgartner, Helv. Chim. Acta 1995, 78, 1490.
31. M. Hugener, H. Heimgartner, Helv. Chim. Acta 1995, 78, 1823.
32. A. D. Hughes, D. A. Price, O. Shishkin, N. S. Simpkins, Tetrahedron Lett. 1996, 37, 7607.
33. J. M. Villalgordo, H. Heimgartner, Helv. Chim. Acta 1993, 76, 2830.
34. P. Wipf, C. Jenny, H. Heimgartner, Helv. Chim. Acta 1987, 70, 1001.
35. R. Luykx, C. B. Bucher, A. Linden, H. Heimgartner, Helv. Chim. Acta 1996, 79, 527.
36. R. A. Breitenmoser, H. Heimgartner, Helv. Chim. Acta 2002, 85, 885.
37. C. Jenny, H. Heimgartner, Helv. Chim. Acta 1986, 69, 374.
38. C. B. Bucher, A. Linden, H. Heimgartner, Helv. Chim. Acta 1995, 78, 935.
39. C. Strässler, A. Linden, H. Heimgartner, Helv. Chim. Acta 1997, 80, 1528.
40. K. A. Brun, A. Linden, H. Heimgartner, Helv. Chim. Acta 2002, 85, 3422.
41. S. Stamm, A. Linden, H. Heimgartner, Helv. Chim. Acta 2003, 86, 1371.
42. M. K. G. Mekhael, Ph.D. thesis, Universität Zürich, 2003.
43. J. Bernstein, R. E. Davies, L. Shimoni, N.-L. Chang, Angew. Chem., Int. Ed. 1995, 34, 1555.
44. C. K. Johnson, ORTEP II, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
45. R. R. Goehring, Y. P. Sachdeva, J. S. Pisipati, M. C. Sleevi, J. F. Wolfe, J. Am. Chem. Soc. 1985, 707, 435.
46. C.-C. Yang, H.-T. Chang, J.-M. Fang, J. Org. Chem. 1993, 58, 3100.
47. K. H. Shaughnessy, B. C. Hamann, J. F. Hartwig, J. Org. Chem. 1998, 63, 6546.
48. L. A. Es'kova, E. V. Petrova, V. K. Turchaninov, M. F. Larin, G. G. Skvortsova, Khim. Geterotxikl. Soedin. 1989, 7, 924.
49. R. Hooft, KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
50. Z. Otwinowski, W. Minor, in 'Methods in Enzymology', Vol. 276, 'Macromolecular Crystallography', Part A, Eds. C. W. Carter Jr., R. M. Sweet, Academic Press, New York, 1997, p. 307.
51. A. Altomare, G. Cascarano, C. Giacovazzo, A. Guagliardi, M. C. Burla, G. Polidori, M. Camalli, SIR92, J. Appl. Crystallogr. 1994, 27, 435.
52. G. M. Sheldrick, SHELXS97, Program for the Solution of Crystal Structures, University of Göttingen, Germany (1997).
53. a) E. N. Maslen, A. G. Fox, M. A. O'Keefe, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6.1.1.1, p. 477;
54. b) D. C. Creagh, W. J. McAuley, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.6.8, p. 219;
55. c) D. C. Creagh, J. H. Hubbell, in 'International Tables for Crystallography', Ed. A. J. C. Wilson, Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 4.2.4.3, p. 200.
56. R. F. Stewart, E. R. Davidson, W. T. Simpson, J. Chem. Phys. 1965, 42, 3175.
57. J. A. Ibers, W. C. Hamilton, Acta Crystallogr. 1964, 17, 781.
58. teXsan: Single Crystal Structure Analysis Software, Version 1.10, Molecular Structure Corporation, the Woodlands, Texas, 1999.