Application of a radical catalysed isomerisation reaction to the synthesis of fused [1,2-a]indoles

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6249-6250

  Caddick, Stephen ^a   Shering, Craig L ^a   Wadman, Sjoerd N ^b  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; SULFONE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DRUG SYNTHESIS; ISOMERISM; REACTION ANALYSIS;

EID: 0030855437     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01378-6     Document Type: Article

References (20)

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2. For reviews of the area: Chatgilialoglu, C. The Chemistry of Sulfones and Sulfoxides: Sulfonyl Radicals 1988, Wiley, New York. Bertrand, M.-P. Org. Prep. Proceed. Int. 1994, 26, 257. See also Gung, J.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 787. Phillips, E. D.; Warren, E. S.; Whitham, G. H. Tetrahedron 1997, 53, 307. Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209
3. For reviews of the area: Chatgilialoglu, C. The Chemistry of Sulfones and Sulfoxides: Sulfonyl Radicals 1988, Wiley, New York. Bertrand, M.-P. Org. Prep. Proceed. Int. 1994, 26, 257. See also Gung, J.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 787. Phillips, E. D.; Warren, E. S.; Whitham, G. H. Tetrahedron 1997, 53, 307. Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209
4. For reviews of the area: Chatgilialoglu, C. The Chemistry of Sulfones and Sulfoxides: Sulfonyl Radicals 1988, Wiley, New York. Bertrand, M.-P. Org. Prep. Proceed. Int. 1994, 26, 257. See also Gung, J.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 787. Phillips, E. D.; Warren, E. S.; Whitham, G. H. Tetrahedron 1997, 53, 307. Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209
5. For reviews of the area: Chatgilialoglu, C. The Chemistry of Sulfones and Sulfoxides: Sulfonyl Radicals 1988, Wiley, New York. Bertrand, M.-P. Org. Prep. Proceed. Int. 1994, 26, 257. See also Gung, J.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 787. Phillips, E. D.; Warren, E. S.; Whitham, G. H. Tetrahedron 1997, 53, 307. Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209
6. For reviews of the area: Chatgilialoglu, C. The Chemistry of Sulfones and Sulfoxides: Sulfonyl Radicals 1988, Wiley, New York. Bertrand, M.-P. Org. Prep. Proceed. Int. 1994, 26, 257. See also Gung, J.; Fuchs, P. L. Tetrahedron Lett. 1997, 38, 787. Phillips, E. D.; Warren, E. S.; Whitham, G. H. Tetrahedron 1997, 53, 307. Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 1209
7. Simpkins, N. S. Sulfones in Organic Synthesis 1993, Pergamon Press, Oxford.
8. Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675. Aboutayab, K.; Caddick, S.; Jenkins, K.; Oshi, S.; Khan, S. Tetrahedron, 1996, 52, 11329.
9. Caddick, S.; Aboutayab, K.; Jenkins, K.; West, R. I. J. Chem. Soc., Perkin Trans. 1 1996, 675. Aboutayab, K.; Caddick, S.; Jenkins, K.; Oshi, S.; Khan, S. Tetrahedron, 1996, 52, 11329.
10. For related work: Harvey, I. W.; Whitham, G. H. J. Chem. Soc., Perkin Trans. 1 1993, 185 and references therein.
11. Caddick, S.; Shering, C. L.; Wadman, S. N. J. Chem. Soc., Chem. Commun. 1997, 171.
12. Radical based methods for indole synthesis: Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083. Jones, K.; Wilkinson, J.; Ewin, R. Tetrahedron Lett. 1994, 35, 7673. Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051.
13. Radical based methods for indole synthesis: Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083. Jones, K.; Wilkinson, J.; Ewin, R. Tetrahedron Lett. 1994, 35, 7673. Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051.
14. Radical based methods for indole synthesis: Ziegler, F. E.; Belema, M. J. Org. Chem. 1997, 62, 1083. Jones, K.; Wilkinson, J.; Ewin, R. Tetrahedron Lett. 1994, 35, 7673. Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051.
15. Caddick, S.; Aboutayab, K.; West, R. I. Synlett 1993, 231. For other radical additions to aromatic sulfones: Ziegler, Y.; Antonia, M. A.; De la Cruz, E.; Galeazzi, E.; Guzman, A.; Bray, B. L.; Greenhouse, R.; Kurz, L. J.; Lustig, D. A.; Maddox, M. L.; Muchowski, J. M. Can. J Chem. 1994, 72, 15.
16. Caddick, S.; Aboutayab, K.; West, R. I. Synlett 1993, 231. For other radical additions to aromatic sulfones: Ziegler, Y.; Antonia, M. A.; De la Cruz, E.; Galeazzi, E.; Guzman, A.; Bray, B. L.; Greenhouse, R.; Kurz, L. J.; Lustig, D. A.; Maddox, M. L.; Muchowski, J. M. Can. J Chem. 1994, 72, 15.
17. Bhawgwat, S. S.; Gude, C. Tetrahedron Lett. 1994, 35, 1847
18. Back, T. G.; Collins, S. Tetrahedron Lett. 1980, 21, 2213
19. 13C NMR, HRMS)
20. Optimal yields obtained with AIBN (1 eq.); the use of 10% gave only slightly diminished yields e.g. for 5 (72%) and 6 (76%).