1-Aminobenzotriazole functionalisation using directed metallation: New routes to chromanes and chromenes using intramolecular benzyne trapping by alcohols

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 15, 2000, Pages 2343-2355

  Knight, David W ^a   Little, Paul B ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; HYDROGEN BONDS; OXIDATION; SYNTHESIS (CHEMICAL);

METALLATION PROCESS;

AROMATIC HYDROCARBONS;

EID: 85047679064     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b001834l     Document Type: Article

References (45)

1. R. W. Hoffmann, Dehydrobenzenes and Cycloalkynes, Academic Press, New York, 1967;
2. J. T. Sharp, in Comprehensive Organic Chemistry, eds. D. H. R. Barton and W. D. Ollis, Pergamon Press, Oxford, 1979, vol. 1, p. 477;
3. M. G. Reinecke, Tetrahedron, 1982, 38, 427;
4. C. J. Moody and G. H. Whitham, Reactive Intermediates, Oxford University Press, 1992;
5. S. V. Kessar, in Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 4, p. 483.
6. For a review of lateral metallation directed by N-Boc groups, see R. D. Clark arid A. Jahangir, Org. React. (N. Y.), 1995, 47, 1.
7. M. A. Birkett, R. G. Giles, D. W. Knight and M. B. Mitchell, J. Chem. Soc., Perkin Trans, 1, 1998, 2301 ;
8. M. A. Birkett, D. W. Knight, P. B. Little and M. B. Mitchell, Tetrahedron, 2000, 56, 1013.
9. C. D. Campbell and C. W. Rees, J. Chem. Soc. (C), 1969, 742, 748 and 752.
10. See also G. W. J. Fleet and I. Fleming, J. Chem. Soc. (C), 1969, 1758.
11. See, for example, C. D. Buttery, D. W. Knight and A. P. Nott, J. Chem Soc., Perkin Trans, 1, 1984, 2839.
12. 1-Aminobenzotriazole 20 is also commercially available but rather expensive.
13. See, for example, M. M. Midland and A. Kazubski, J. Org. Chem., 1982, 47, 2814;
14. M. Nishizawa, M. Yamada and R. Noyori, Tetrahedron Lett., 1981, 22, 247.
15. Chromenes, Chromanones and Chromones, ed. G. P. Ellis, Wiley, New York, 1977.
16. G. Burrell, J. M. Evans, M. S. Hadley, F. Hicks and G. Stemp, Bioorg. Med. Chem. Lett., 1994, 4, 1285;
17. G. Burrell, J. M. Evans, F. Hicks and G. Stemp, Bioorg. A fed Chem. Lett., 1993, 3, 999;
18. F. Cassidy, J. M. Evans, M. S. Hadley, A. H. Haladij, P. E. Leech and G. Stemp, J. Med Chem., 1992, 35, 1623;
19. J. M. Evans and G. Stemp, Chem. Br., 1991, 27, 439 and references cited therein.
20. I. Iwai and J. Ide, Chem. Pharm. Bull., 1962, 10, 926;
21. I. Iwai and J. Ide, Chem. Pharm. Bull., 1963, 11, 1042.
22. See, for example, L. Crombie, W. M. Bandaranayake and D. A. Whiting, J. Chem. Soc. (C), 1971, 804 and 811;
23. L. Crombie and R. Ponsford, J. Chem. Soc. (C), 1971, 788.
24. L. Crombie, Nat. Prod Rep., 1984, 1, 3;
25. L. Crombie and D. A. Whiting, Phytochemistry, 1998, 49, 1479 and references cited therein.
26. For a preliminary communication, see D. W. Knight and P. B. Little, Tetrahedron Lett., 1998, 39, 5105.
27. F. Krollpfeiffer, A. Rosenburg and C. Muhlhausen, Annalen, 1935, 515, 113.
28. J. T. Klein, L. O. Davis, G. E. Olsen, G. S. Wong and F. P. Huger, J. Med. Chem., 1996, 39, 570.
29. For a review of the synthetic utility of hydroxylamine-O-sulfonic acid, see R. G. Wallace, Aldrichimica Acta, 1980, 13, 3.
30. M. Schlosser, Pure Appl. Chem., 1988, 60, 1627 and references cited therein.
31. G. Chaput, G. Jeminet and J. Juillard, Can. J. Chem., 1975, 53, 2240;
32. J.-M. Lehn and J. P. Sauvage, J. Am. Chem. Soc., 1975, 97, 6700.
33. For excellent summaries of this effect, see S. E. Denmark, J. P. Edwards and O. Nicaise, J. Org. Chem., 1993, 58, 569;
34. D. L. Comins and H. Hong, J. Org. Chem., 1996, 61, 391.
35. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 4467;
36. K. Sonogashira, Comprehensive Organic Synthesis, eds. B. M. Trost and I. Fleming, Pergamon Press, Oxford, 1991, vol. 3, p. 521 and references cited therein.
37. C. E. Castro and R. D. Stevens, J. Org. Chem., 1963, 28, 2163.
38. H. E. Ensly, S. Mahedevan and J. Mague, Tetrahedron Lett., 1996, 37, 6255.
39. H. Lindlar, Helv. Chim. Acta, 1952, 35, 446;
40. D. J. Cram and N. L. Allinger, J. Am. Chem. Soc., 1956, 78, 2518;
41. J. Ragaram, A. P. S. Narula, H. P. S. Chawla and S. Dev, Tetrahedron, 1983, 39, 2315.
42. F. Sato, H. Ishikawa and M. Sato, Tetrahedron Lett., 1981, 22, 85.
43. R. D. Rieke, P. T.-J. Li, T. P. Burns and S. T. Uhm, J. Org. Chem., 1981, 46, 4323;
44. W.-N. Chou, D. L. Clark and J. B. White, Tetrahedron Lett., 1991, 32, 299.
45. W. L. F. Armarego and D. D. Perrin, Purification of Laboratory Chemicals, Butterworth Heinemann, Oxford, 1996.