Intramolecular Schmidt reaction of acyl chlorides with alkyl azides: Rapid access to fused polycyclic nitrogen-containing heterocycles via a multistep one-pot transformation

Organic Letters

Volumn 14, Issue 22, 2012, Pages 5796-5799

  Gu, Peiming ^a   Kang, Xiao Yan ^a   Sun, Jian ^a   Wang, Bao Juan ^a   Yi, Ming ^a   Li, Xue Qiang ^a   Xue, Ping ^a   Li, Rui ^a  

^a NINGXIA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84869191965     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302890a     Document Type: Article

References (34)

1. Wolff, H. Org. React. 1946, 3, 307-336
2. Koldobskii, G. I.; Ostrovskii, V. A.; Gidaspov, B. V. Russ. Chem. Rev. 1978, 47, 1084-1094
3. Shioiri, T. Comp. Org. Synth. 1991, 6, 795-828
4. Wrobleski, A.; Coombs, T. C.; Huh, C. W.; Li, S.-W.; Aubé, J. Org. React. 2012, 78, 1-320
5. Aubé, J.; Milligan, G. L. J. Am. Chem. Soc. 1991, 113, 8965-8966
6. Milligan, G. L.; Mossman, C. J.; Aubé, J. J. Am. Chem. Soc. 1995, 117, 10449-10459
7. Pearson, W. H.; Schkeryantz, J. M. Tetrahedron Lett. 1992, 33, 5291-5294
8. Pearson, W. H.; Walavalkar, R.; Schkeryantz, J. M.; Fang, W.; Blickensdorf, J. D. J. Am. Chem. Soc. 1993, 115, 10183-10194
9. For a selected review, see: Aubé, J. In Organic Azides: Synthesis and Applications; Brase, S.; Banert, K., Eds.; Wiley: Weinheim, 2009; pp 191-237.
10. 3 in the presence of sulfinic acid afforded cyclic amide, which was different in form from the products in this paper; see: Datta, S. K.; Grundmann, C.; Bhattacharyya, N. K. J. Chem. Soc. (C) 1970, 2058.
11. Lee, H.-L.; Aubé, J. Tetrahedron 2007, 63, 9007-9015
12. Newcomb, M.; Esker, J. L. Tetrahedron Lett. 1991, 32, 1035-1038
13. Esker, J. L.; Newcomb, M. J. Org. Chem. 1993, 58, 4933-4940
14. Orito, K.; Miyazawa, M.; Nakamura, T.; Horibata, A.; Ushito, H.; Nagasaki, H; Yuguchi, M.; Yamashita, S.; Yamazaki, T.; Tokuda, M. J. Org. Chem. 2006, 71, 5951-5958
15. Bertrand, M. B.; Neukom, J. D.; Wolfe, J. P. J. Org. Chem. 2008, 73, 8851-8860
16. Brenzovich, W. E., Jr.; Benitez, D.; Lackner, A. D.; Shunatona, H. P.; Tkatchouk, E.; Goddard, W. A., III; Toste, F. D. Angew. Chem., Int. Ed. 2010, 49, 5519-5522
17. Mai, D. N.; Wolfe, J. P. J. Am. Chem. Soc. 2010, 132, 12157-12159
18. Golden, J. E.; Aubé, J. Angew. Chem., Int. Ed. 2002, 41, 4316-4318
19. Zeng, Y.; Reddy, D. S.; Hirt, E.; Aubé, J. Org. Lett. 2004, 6, 4993-4995
20. Zeng, Y.; Aubé, J. J. Am. Chem. Soc. 2005, 127, 15712-15713
21. Gu, P.; Zhao, Y.-M.; Tu, Y. Q.; Ma, Y.; Zhang, F. Org. Lett. 2006, 8, 5271-5273
22. Frankowski, K. J.; Golden, J. E.; Zeng, Y.; Lei, Y.; Aubé, J. J. Am. Chem. Soc. 2008, 130, 6018-6024
23. Zhao, Y.-M.; Gu, P.; Tu, Y.-Q.; Fan, C.-A.; Zhang, Q. Org. Lett. 2008, 10, 1763-1766
24. Huh, C. W.; Somal, G. K.; Katz, C. E.; Pei, H.; Zeng, Y.; Douglas, J. T.; Aubé, J. J. Org. Chem. 2009, 74, 7618-7626
25. Meyer, A. M.; Katz, C. E.; Li, S.-W.; Velde, D. V.; Aubé, J. Org. Lett. 2010, 12, 1244-1247
26. Chen, Z.-H.; Tu, Y.-Q.; Zhang, S.-Y.; Zhang, F.-M. Org. Lett. 2011, 13, 724-727
27. Huh, C. W.; Schroeder, C.; Singh, G.; Aubé, J. J. Org. Chem. 2011, 76, 3160-3165
28. Li, Z.; Jin, Z.; Huang, R. Synthesis 2001, 16, 2365-2378
29. Gellert, E. J. Nat. Prod. 1982, 45, 50-73
30. Bick, I. R. C.; Sinchai, W. The Alkaloids 1982, 19, 193-220
31. Govindachari, T. R.; Viswanathan, N. Heterocycles 1978, 11, 587-613
32. Jin, Z. Nat. Prod. Rep. 2009, 26, 363-381 and previous reviews in this series
33. Hoshino, O. The Alkaloids 1998, 51, 323-424
34. Martin, S. F. The Alkaloids 1988, 30, 251-376