Synthesis and reactivity of a novel group of hydroxylamine-containing 2π- and 4π-components

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 5, 1998, Pages 847-852

  Pearce, Alan J ^a   Walter, Daryl S ^b   Frampton, Christopher S ^b   Gallagher, Timothy ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748628268     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a708380g     Document Type: Article

References (54)

1. (a) J. B. Hester, A. D. Rudzik and P. F. VonVoigtlander, J. Med. Chem., 1980, 23, 392;
2. (b) K. R. Scott, C. J. Alt, M. Kemp, E. Hayes and V. G. Telang, J. Pharm. Sci., 1984, 73, 1531;
3. (c) G. Johnson, P. A. Boxer, J. T. Drummond, D. K. Boyd and R. J. Anderson, Arzneim.-Forsch., 1989, 39, 432;
4. (d) J. M. J. Tronchet, G. Zosimo-Landolfo, G. Galland-Barrera and N. Dolatshahi, Carbohydr. Res., 1990, 204, 145;
5. (e) A. Ejima, H. Teresawa, M. Sugimori, S. Ohsuki, K. Matsumoto, Y. Kawato, M. Yasuoka and H. Tagawa, Chem. Pharm. Bull., 1992, 40, 683;
6. (f) J. Stanek, J. Frei, H. Mett, P. Schneider and U. Regenass, J. Med. Chem., 1992, 35, 1339;
7. (g) L. Maier and H. Sporri, Phosphorus Sulfur, 1992, 70, 49;
8. (h) J. Guo, Y. Q. Wu, D. Rattendi, C. J. Bacchi and P. M. Woster, J. Med. Chem., 1995, 38, 1770.
9. (a) J. N. Kim, K. M. Kim and E. K. Ryu, Synth. Commun., 1992, 22, 1427;
10. (b) T. Fuji, C. C. Wu and S. Yamada, Chem. Pharm. Bull., 1967, 15, 345;
11. (c) T. Henmi, T. Sakamoto and Y. Kikugawa, Org. Prep. Proced. Int., 1994, 26, 111;
12. (d) A. T. Fuller and H. King, J. Chem. Soc., 1947, 963;
13. (e) S.-H. Kim, D. Augeri, D. Yang and D. Kahne, J. Am. Chem. Soc., 1994, 116, 1766;
14. (f) A. Fruchier, V. Moragues, C. Pétrus and F. Pétrus, Bull. Soc. Chim. Fr., 1984, 11, 173;
15. (g) I. A. Motorina, F. Parly and D. Grierson, Synlett, 1996, 389.
16. J. B. Hendrickson, S. Okano and R. K. Bloom, J. Org. Chem., 1969, 34, 3434.
17. (a) E. L. Schumann, L. A. Paquette, R. V. Heinzelman, D. P. Wallach, J. P. DaVanzo and M. E. Grieg, J. Med. Pharm. Chem., 1962, 5, 464;
18. (b) A. D. Zorina, V. F. Martynov, L. G. Matyukhina and I. A. Saltykova, J. Gen. Chem. USSR (Engl. Transl.), 1982, 52, 204;
19. (c) A. Balsamo, G. Broccali, A. Lapucci, B. Macchia, F. Macchia, E. Orlandini and A. Rossello, J. Med. Chem., 1989, 32, 1398.
20. Y. Endo, K. Shudo and T. Okamoto, Synthesis, 1980, 461.
21. For recent and representative examples, see: (alkylation) S. D. Young and P. P. Tamburini, J. Am. Chem. Soc., 1989, 111, 1933;
22. V. Dupont, A. Lecoq, J.-P. Mangeot, A. Aubry, G. Boussard and M. Marraud, J. Am. Chem. Soc., 1993, 115, 8898;
23. D. V. Patel, M. G. Young, S. P. Robinson, L. Hunihan, B. J. Dean and E. M. Gordon, J. Med. Chem., 1996, 39, 4197;
24. (reductive amination) F.-C. Huang, T. S. Shoupe, C. J. Lin, T. D. Y. Lee, W.-K. Chan, J. Tan, M. Schnapper, J. T. Suh, R. J. Gordon, P. A. Sonnino, C. A. Sutherland, R. G. Vaninwegen and S. M. Coutts, J. Med. Chem., 1989, 32, 1836;
25. S. Venkatraman, R. J. Roon, M. K. Schulte, J. F. Koerner and R. L. Johnson, J. Med. Chem., 1994, 37, 3939;
26. (acylation) R. A. Farr, P. Bey, P. S. Sunkara and B. J. Lippert, J. Med. Chem., 1989, 32, 1879. See also reference 1.
27. (a) E. J. Breaux, J. Heterocycl. Chem., 1986, 23, 463;
28. (b) S. Bottle, W. K. Busfield, I. D. Jenkins, B. W. Skelton, A. H. White, E. Rizzardo and D. H. Solomon, J. Chem. Soc., Perkin Trans. 2, 1991, 1001;
29. (c) S. D. Pastor and E. T. Hessell, J. Org. Chem., 1988, 53, 5776;
30. (d) E. Winterfeldt and W. Krohn, Chem. Ber., 1969, 102, 2336.
31. I. Vlattas, L. Della Vecchia and J. J. Fitt, J. Org. Chem., 1973, 38, 3749.
32. (a) W. H. Watanabe and L. E. Conlon, J. Am. Chem. Soc., 1957, 79, 2828;
33. (b) H.-J. Gi, Y. Xiang, R. F. Schinazi and K. Zhao, J. Org. Chem., 1997, 62, 88;
34. (c) E. Bayer and K. Geckeler, Angew. Chem., Int. Ed. Engl., 1979, 18, 533.
35. L. W. Jones and M. C. Sneed, J. Am. Chem. Soc., 1917, 39, 674.
36. L. C. Chan, PhD Thesis, University of Bath, 1992.
37. (a) J. F. Arens, Adv. Org. Chem., 1960, 2, 117;
38. (b) T. L. Jacobs and W. P. Tuttle, J. Am. Chem. Soc., 1949, 71, 1313;
39. (c) T. L. Jacobs and W. R. Scott, J. Am. Chem. Soc., 1953, 75, 5497.
40. K. Afarinkia, V. Vinader, T. D. Nelson and G. H. Posner, Tetrahedron, 1992, 48, 9111.
41. V. Kvita and H. Sauter, Helv. Chim. Acta, 1990, 73, 883.
42. (a) A. N. Boa, S. E. Booth, D. A. Dawkins, P. R. Jenkins, J. Fawcett and D. R. Russell, J. Chem. Soc., Perkin Trans. 1, 1993, 1277;
43. (b) O. Moriya, Y. Urata and T. Endo, J. Chem. Soc., Chem. Commun., 1991, 17.
44. N. A. Petasis, S.-P. Lu, E. I. Bzowej, D.-K. Fu, J. P. Staszewski, I. Akritopoulou-Zane, M. A. Patane and Y.-H. Hu, Pure Appl. Chem., 1996, 68, 667.
45. W. J. Bailey and E. W. Cummins, J. Am. Chem. Soc., 1954, 76, 1932.
46. (a) E. G. Kataev, T. G. Mannafov, E. G. Berdnikov and O. A. Komarovskaya, Zh. Org. Khim., 1973, 9, 1983;
47. (b) B. Lindgren, Acta Chem. Scand., Ser. B, 1977, 31, 1.
48. P. Rajagopalan, B. G. Advani and C. N. Talaty, Org. Synth., 1973, Coll. Vol. V, 504.
49. C. F. Huebner, E. Donoghue, L. Dorfman, F. A. Stuber, N. Danieli and E. Wenkert, Tetrahedron Lett., 1966, 1185.
50. S. H. Reich, M. A. M. Fuhry, D. Nguyen, M. J. Pino, K. M. Welsh, S. Webber, C. A. Janson, S. R. Jordan, D. A. Matthews, W. W. Smith, C. A. Bartlett, C. L. J. Booth, S. M. Hermann, E. F. Howland, C. A. Morse, R. W. Ward and J. White, J. Med. Chem., 1992, 35, 847.
51. C. Graebe and J. Buenzod, Ber., 1899, 32, 1993.
52. TEXSAN Single Crystal Structure Analysis Software, Version 1.6, Molecular Structure Corporation, The Woodlands, TX 77381, USA, 1993.
53. J. Cosier and A. M. Glazer, J. Appl. Crystallogr., 1986, 19, 105.
54. G. M. Sheldrick, SHELXTL, Program for Crystal Structure Solution and Refinement, University of Göttingen, Germany, 1993.