Synthesis and cross-coupling reactions of 7-azaindoles via a new donor-acceptor cyclopropane

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3777-3779

  Zheng, Xiaomei ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748598708     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061379i     Document Type: Article

References (16)

1. (a) Gribble, G. W. In Comprehensive Heterocyclic Chemistry, 2nd ed.; Pergammon Press: New York. 1996; Vol. 2, pp 203-257.
2. (b) Snieckus V. A. In The Alkaloids: Academic Press: New York. 1968; Vol. 11, Chapter 1.
3. For a recent synthesis of 7-azaindoles with leading references concerning both synthesis and pharmaceutical aspects, see: Schirok, H. Synlett 2005, 1255-1258.
4. Anderson, R. J.; Hill, J. B.; Morris, J. C. J. Org. Chem. 2005, 70, 6204-6212 and references therein.
5. Yang, A.; Zadjura, L.; D'Arienzo, A. M.; Santone, K.; Llunk, L.; Green, D.; Lin, P.-F.; Colonno, R.; Wang, T.; Neanwell, N.; Hansel, S. Biopharm. Drug Dispos. 2005, 26, 387-402.
6. O'Neill, D. J.; Shen, L.; Prouty, C.; Conway, B. R.; Westover, L.; Xu, J. Z.; Zhang, H.-C.; Maryanoff, B. E.; Murray, W. V.; Demarest, K. T.; Kuo, G.-H. Bioorg. Med. Chem. 2004, 12, 3167-3185.
7. (a) Wanapun, D.; Van Gorp, K. A.; Mosey, N. J.; Kerr, M. A.; Woo, T. K. Can. J. Chem. 2005, 83, 1752-1767.
8. (b) Carson, C. A.; Kerr, M. A. J. Org. Chem. 2005, 70, 8242-8244.
9. (c) Young, I. S.; Williams, J. L.; Kerr, M. A. Org. Lett. 2005, 7, 953-955.
10. (d) Ganton, M. D.; Kerr, M. A. J. Org. Chem. 2004, 69, 8554-8557.
11. (e) Young, I. S.; Kerr, M. A. Org. Lett. 2004, 6, 139-141.
12. (f) Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023-3026.
13. The activation of amides with triflic anhydride of pyridine has been well documented. See, for example: (a) DeRoy, P. L.; Charette, A. B. Org. Lett. 2003, 5, 4163-4165 and references therein,
14. (b) Mahuteau-Betzer, F.; Ding, P.-Y.; Ghosez, L. Helv. Chim. Acta 2005, 88, 2022-2031 and references therein.
15. One of the reviewers has suggested the use of a bulkier rhodium catalyst to suppress suspected carbenoid dimerization side reactions. This will be explored in future studies.
16. The relative stereochemistry of 17 was not determined because the stereochemistry would have been lost upon success in the intended reaction.