Bromoethylsulfonium salt-a more effective annulation agent for the synthesis of 6- and 7-membered 1,4-heterocyclic compounds

Organic Letters

Volumn 11, Issue 2, 2009, Pages 257-260

  Yar, Muhammad ^a   McGarrigle, Eoghan M ^a   Aggarwal, Varinder K ^a  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AZEPINE DERIVATIVE; HETEROCYCLIC COMPOUND; INORGANIC SALT; MORPHOLINE; MORPHOLINE DERIVATIVE; SULFONIUM DERIVATIVE;

ARTICLE; CHEMISTRY; SYNTHESIS;

AZEPINES; HETEROCYCLIC COMPOUNDS; MORPHOLINES; SALTS; SULFONIUM COMPOUNDS;

EID: 61449177950     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8023727     Document Type: Article

References (45)

1. For a review see: (a) Wijtmans, R.; Vink, M. K. S.; Schoemaker, H. E.; van Delft, F. L.; Blaauw, R. H.; Rutjes, F. P. J. T. Synthesis 2004, 641-662. For recent examples see:
2. (b) Breuning, M.; Winnacker, M.; Steiner, M. Eur. J. Org. Chem. 2007, 2100-2106.
3. (c) D'hooghe, M.; Vanlangendonck, T.; Törnroos, K. W.; De Kimpe, N. J. Org. Chem. 2006, 71, 4678-4681.
4. (d) Pedrosa, R.; Andres, C.; Mendiguchia, P.; Nieto, J. J. Org. Chem. 2006, 71, 8854-8863.
5. (e) Wilkinson, M. C. Tetrahedron Lett. 2005, 46, 4773-4775.
6. (f) Lanman, B. A.; Myers, A. G. Org. Lett. 2004, 6, 1045-1047.
7. (a) Chiu, H.; Lin, Y. C.; Cheng, C. Y.; Tsai, M. C.; Yu, H. C. Bioorg. Med. Chem. Lett. 2001, 9, 383-393.
8. (b) Kashima, C.; Harada, K. J. Chem. Soc., Perkin. Trans. 1 1988, 1521-1526.
9. (c) Liang, P. H.; Hsin, L. W.; Cheng, C. Y. Bioorg. Med. Chem. 2002, 10, 3267-3276.
10. (d) Sakai, K.; Yoneda, N. Chem. Pharm. Bull. 1981, 29, 1554-1560.
11. (e) Bhatt, U.; Just, G. Helv. Chim. Acta 2000, 83, 722-727.
12. For vinyl sulfonium salts see: (a) Kokotos, C. G.; McGarrigle, E. M.; Aggarwal, V. K. Synlett 2008, 2191-2195.
13. (b) Unthank, M. G.; Tavassoli, B.; Aggarwal, V. K. Org. Lett. 2008, 10, 1501-1504.
14. (c) Unthank, M. G.; Hussain, N.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2006, 45, 7066-7069;
15. Angew. Chem. 2006, 118, 7224-7227.
16. (d) Kim, K.; Jimenez, L. S. Tetrahedron: Asymmetry 2001, 12, 999-1005, and references therein,
17. (e) Wang, Y.; Zhang, W.; Colandrea, V. J.; Jimenez, L. S. Tetrahedron 1999, 55, 10659-10672. For epoxidation reactions of butadienylsulfonium salts, see:
18. (f) Rowbottom, M. W.; Mathews, N.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1998, 3927-3929. For recent examples of the application of vinyl phosphonium salts see:
19. (g) Kumam, S.; Shaw, D. M.; Ley, S. V. Chem. Commun. 2006, 3211-3213.
20. (a) Yar, M.; McGarrigle, E. M.; Aggarwal, V. K. Angew. Chem., Int. Ed. 2008, 47, 3784-3786.
21. Angew. Chem. 2008, 120, 3844-3846; For an application see:
22. (b) Hansen, M.; Illa, O.; McGarrigle, E. M.; Aggarwal, V. K. Chem. Asian J. 2008, 3, 1657-1663.
23. For a recent review on the use of ylides in reactions that form rings other than 3-membered rings see: Sun, X.-L.; Tang, Y. Acc. Chem. Res. 2008, 41, 937-948.
24. This salt is now commercially available from Aldrich.
25. Nucleophiles with two acidic protons on the same atom have been shown to react with vinyl sulfonium salts to give 3-membered rings (e.g., primary amines give aziridines): see ref 4a and (a) Gosselck, J.; Béress, L.; Schenk, H. Angew. Chem., Int. Ed. Engl. 1966, 5, 596-597; Angew. Chem. 1966, 78, 606.
26. (b) Johnson, C. R.; Lockard, J. P. Tetrahedron Lett. 1971, 12, 4589-4592.
27. (c) Takaki, K.; Agawa, T. J. Org. Chem. 1977, 42, 3303-3304.
28. (d) Matsuo, J.; Yamanaka, H.; Kawana, A.; Mukaiyama, T. Chem. Lett. 2003, 32, 392-393. Where the nucleophile can be resonance-stabilized forming an enolate, 5-membered rings have also been obtained:
29. (e) Braun, H.; Huber, G. Tetrahedron Lett. 1976, 17, 2121-2124.
30. (f) Batty, J. W.; Howes, P. D.; Stirling, C. J. M. J. Chem. Soc., Perkin 1 1973, 65-68; ref 7b.
31. Weinreb, S. M.; Demko, D. M.; Lessen, T. A. Tetrahedron Lett. 1986, 27, 2099-2102.
32. (a) Sladojevich, F.; Trabocchi, A.; Guarna, A. J. Org. Chem. 2007, 72, 4254-4257.
33. (b) Levin, J. I.; Chen, J. M.; Laakso, L. M.; Du, M.; Du, X.; Venkatesan, A. M.; Sandanayaka, V.; Zask, A.; Xu, J.; Xu, W.; Zhang, Y.; Skotnicki, J. S. Bioorg. Med. Chem. Lett. 2005, 15, 4345-4349.
34. (c) Almstead, N. G.; Bradley, R. S.; Pikul, S.; De, B.; Natchus, M. G.; Taiwo, Y. O.; Gu, F.; Williams, L. E.; Hynd, B. A.; Janusz, M. J.; Dunaway, C. M.; Mieling, G. E. J. Med. Chem. 1999, 42, 4547-4562.
35. (c) Chiba, J.; Machinaga, N.; Takashi, T.; Ejima, A.; Takayama, G.; Yokoyama, M.; Nakayama, A.; Baldwin, J. J.; McDonald, E.; Saionz, K. W.; Swanson, R.; Hussain, Z.; Wong, A. Bioorg. Med. Chem. Lett. 2005, 15, 41-45.
36. In our previous study, it was found that amides and carbamates were not compatible with this methodology. See ref 4a for details.
37. In the case of 1,2-aminothiols primary amines can be employed without aziridine formation since the more nucleophilic thiol adds to the vinyl sulfonium salt first.
38. Mechanistically it is unclear why 3.5 equiv of NaH are required, but the use of less NaH gave lower yields of cyclized product, together with protonated 2 [see ref 4a],
39. For leading references on 7-membered heterocycles see: Bremner, J. B.; Samosorn, S. In Progress in Heterocydic Chemistry; Gribble, G. W., Joule, J. A., Eds.; Elsevier: Amsterdam, 2008; Vol. 19, Chapter 7.
40. Costantino, L.; Barlocco, D. Curr. Med. Chem. 2006, 13, 65-85.
41. Lee, S.-C.; Park, S. B. Chem. Commun. 2007, 3714-3716.
42. Grunewald, G. L.; Dahanukar, V. H.; Ching, P.; Criscione, K. R. J. Med. Chem. 1996, 39, 3539-3546.
43. Ishihara, Y.; Hirai, K.; Miyamoto, M.; Goto, G. J. Med. Chem. 1994, 37, 2292-2299.
44. Welmaker, G. S.; Sabalski, J. E. Tetrahedron Lett. 2004, 45, 4851-4854.
45. See reference 14 for leading references.