Synthesis of α,α-diarylacetamides from benzyl aryl ketones using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate

Tetrahedron Letters

Volumn 52, Issue 24, 2011, Pages 3158-3161

  Kitamura, Mitsuru ^a   Miyagawa, Satoshi ^a   Okauchi, Tatsuo ^a  

^a KYUSHU INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Amide formation; Azides; Diazonium salts; Guanidine

Indexed keywords

2 AZIDO 1,3 DIMETHYLIMIDAZOLINIUM HEXAFLUOROPHOSPHATE; ACETAMIDE DERIVATIVE; ALUMINUM LITHIUM HYDRIDE; BENZENE DERIVATIVE; CARBONYL DERIVATIVE; DIAZONIUM COMPOUND; FLUOROPHOSPHATE; IMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

AMIDATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 79956059900     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.04.042     Document Type: Article

References (35)

1. R.R. Burtner, and J.W. Cusic J. Am. Chem. Soc. 1943 262
2. J.Y.P. Chen, and H. Beckman J. Pharmacol. Exp. Ther. 104 1952 269
3. Opionoid: J. Klosa Arch. Pharm. 288 1955 42
4. Wals, L.; Cooymans, B. U.S. Patent 4 898 873, 1990.
5. A. Barber, G.D. Bartoszyk, H.M. Bender, R. Gottschlich, H.E. Greiner, J. Harting, F. Mauler, K.-O. Minck, R.D. Murray, M. Simon, and C.A. Seyfried Br. J. Pharmacol. 113 1994 1317
6. Pein, E.; Ritter, H.; Laven, R. U.S. Patent 5 897 8755, 1999.
7. J. Liebig Liebigs Ann. Chem. 25 1838 27
8. S. Selman, and J.F. Eastham Q. Rev., Chem. Soc. 14 1960 221
9. For a review, see: C.C.C. Johansson, and T.J. Colacot Angew. Chem., Int. Ed. 49 2010 676
10. W.A. Moradi, and S.L. Buchwald J. Am. Chem. Soc. 123 2001 7996
11. C.G. Screttas, and B.R. Steele J. Org. Chem. 54 1989 1013
12. M.J. Earle, R.A. Fairhurst, and H. Heaney Tetrahedron Lett. 32 1991 6171
13. M. Periasamy, N. KishoreBabu, and K.N. Jayakumar Tetrahedron Lett. 44 2003 8939
14. C. Peng, W. Zhang, G. Yan, and J. Wang Org. Lett. 11 2009 1667
15. For reviews see: M. Regitz Angew. Chem., Int. Ed. Engl. 6 1967 733
16. M. Regitz Synthesis 1972 351
17. T. Ye, and M.A. McKervey Chem. Rev. 94 1994 1091
18. M.P. Doyle, T. Ye, and M.A. McKervey Modern Catalytic Methods for Organic Synthesis with Diazo Compounds 1998 John Wiley & Sons New York
19. Z. Zhang, and J. Wang Tetrahedron 64 2008 6577
20. R.L. Danheizer, R.F. Miller, R.G. Brisbois, and S.Z. Park J. Org. Chem. 55 1990 1959
21. M. Regitz Tetrahedron Lett. 5 1964 1403
22. J.B. Hendrickson, and W.A. Wolf J. Org. Chem. 33 1968 3610
23. D.A. Evans, T.C. Britton, J.A. Ellman, and R.L. Dorow J. Am. Chem. Soc. 112 1990 4011
24. M. Ma, C. Li, L. Peng, F. Xie, X. Zhang, and J. Wang Tetrahedron Lett. 46 2005 3927
25. Diazo-transfer reaction with 2-azido-1,3-dimethylimidazolinium salt, see: M. Kitamura, N. Tashiro, S. Miyagawa, and T. Okauchi Synthesis 2011 1037
26. M. Kitamura, N. Tashiro, and T. Okauchi Synlett 2009 2943
27. For the reaction with 2-azido-1,3-dimethylimidazolinium salt, see: M. Kitamura, M. Yano, N. Tashiro, S. Miyagawa, M. Sando, and T. Okauchi Eur. J. Org. Chem. 2011 458
28. M. Kitamura, N. Tashiro, R. Sakata, and T. Okauchi Synlett 2010 2503
29. M. Kitamura, N. Tashiro, Y. Takamoto, and T. Okauchi Chem. Lett. 39 2010 732
30. M. Okubo, Y. Morigami, and R. Suenaga Bull. Chem. Soc. Jpn 53 1980 3029
31. 3O (307.17): C, 74.24: H, 6.89: N, 13.67. Found: C, 74.09: H, 6.89: N, 13.53.
32. 13NO (211.1): C, 79.59: H, 6.20: N, 6.63. Found: C, 79.47: H, 6.30: N, 6.65.
33. Similar intermediates have been previously proposed, see: N. Kawai, and T. Shioiri Chem. Pharm. Bull. 31 1983 2564
34. H. Vogt, T. Baumann, M. Nieger, and S. Bräse Eur. J. Org. Chem. 2006 5315
35. For an example of the failure of a 1,2-anionotropic rearrangement with a bulky electron rich aryl group, see: T. Saito, T. Suzuki, M. Morimoto, C. Akiyama, T. Ochiai, K. Takeuchi, T. Matsumoto, and K. Suzuki J. Am. Chem. Soc. 120 1998 11633