Anionic N-fries rearrangement of N-carbamoyl diarylamines to anthranilamides. Methodology and application to acridone and pyranoacridone alkaloids

Organic Letters

Volumn 8, Issue 6, 2006, Pages 1133-1136

  MacNeil, Stephen L ^a,b   Wilson, Brian J ^a,c   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b WILFRID LAURIER UNIVERSITY   (Canada)

^c GLAXOSMITHKLINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOBENZAMIDE; ACRIDINE DERIVATIVE; ACRIDONE; ALKALOID; AMINE; ANTHRANILIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; SYNTHESIS;

ACRIDINES; ALKALOIDS; AMINES; ANTHRANILIC ACIDS; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE;

EID: 33646452253     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol053162e     Document Type: Article

References (58)

1. (a) Anionic ortho-Fries: Sibi, M. P.; Snieckus, V. J. Org. Chem. 1983, 48, 1935-1937.
2. (b) Vinylogous anionic ortho-Fries: Kalinin, A. V.; Miah, M. A. J.; Chattopadhyay, S.; Tsukazaki, M.; Wicki, M.; Nguen, T.; Coelho, A. L.; Kerr, M.; Snieckus, V. Synlett 1997, 7, 839-841.
3. 2 translocation: Chauder, B. A.; Kalinin, A. V.; Taylor, N. J.; Snieckus, V. Angew. Chem., Int. Ed. 1999, 38, 1435-1438.
4. (d) Remote anionic Fries: Wang, W.; Snieckus, V. J. Org. Chem. 1992, 57, 424-426.
5. 2 translocation: Zhang, P.; Gawley, R. E. J. Org. Chem. 1993, 12, 3222-3223.
6. (f) Carbamoyl Baker-Venkatarman reaction: Kalinin, A. V.; da Silva, A. J. M.; Lopes, C. C.; Lopes, R. S. C.; Snieckus, V. Tetrahedron Lett. 1998, 39, 4995-4998.
7. (g) Anionic Friedel-Crafts equivalents: To acridones: MacNeil, S. L.; Gray, M.; Briggs, L. E.; Li, J. J.; Snieckus, V. Synlett 1998, 4, 419-421.
8. MacNeil, S. L.; Gray, M.; Briggs, L. E., Snieckus, V. In preparation.
9. (h) To xanthones: Familoni, O. B.; Ionica, I.; Bower, J. F.; Snieckus, V. Synlett 1997, 9, 1081-1083.
10. To thiaxanthones: Beaulieu, F.; Snieckus, V. J. Org. Chem. 1994, 59, 6508-6509.
11. (j) To phosphorinones: Gray, M.; Chapell, B. J.; Taylor, N. J.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1996, 35, 1558-1560.
12. (k) Anionic O→α- and β-vinyl carbamoyl translocation: Reed, M. A.; Chang, M. T.; Snieckus, V. Org. Lett. 2004, 6, 2297-2300.
13. (a) Snieckus, V. Chem. Rev. 1990, 90, 879-933.
14. (b) Hartung, C. G.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 330-367.
15. Whisler, M. C.; MacNeil, S.; Snieckus, V.; Beak, P. Angew. Chem., Int. Ed. 2004, 43, 2206-2225.
16. For a closely related example, see: Iwao, M.; Reed, N.; Snieckus, V. J. Am. Chem. Soc. 1982, 104, 5531-5533.
17. For general effects of m-EDG on Friedel-Crafts chemistry, see: Taylor, R. In Electrophilic Aromatic Substitution; Wiley: New York, 1990; p 236.
18. For examples, see: Sargent, M. V. J. Chem. Soc., Perkin Trans. 1 1987, 2553.
19. Fu, J.-m.; Zhao, B.-p.; Sharp, M. J.; Snieckus, V. Can. J. Chem. 1994, 72, 227-236.
20. Sharp, M. J. M.Sc. Thesis, University of Waterloo, 1986.
21. 2: Cambie, R. C.; Plamer, B. D. Aust. J. Chem. 1982, 35, 827-837 and references therein.
22. Melvin, L. S. Tetrahedron Lett. 1981, 22, 3375-3376.
23. Dhawan, B.; Redmore, D. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 61, 183-187 and references therein.
24. (b) ArOCOR: Hellwinkel, D.; Lämmerzahl, F.; Hofmann, G. Chem. Ber. 1983, 116, 3375-3405 and references therein.
25. 3: Billedeau, R. J.; Sibi, M. P.; Snieckus, V. Tetrahedron Lett. 1983, 24, 4515-4518.
26. 2: Jardine, A. M.; Vather, S. M. J. Org. Chem. 1988, 53, 3983-3985.
27. (e) ArN(R)COR: Horne, S.; Rodrigo, R. J. Chem. Soc., Chem. Commun. 1991, 1046-1048.
28. Reference 7b.
29. 3: ref 7b.
30. 2-Ph)Ar′: Hellwinkel, D.; Supp, M. Chem. Ber. 1976, 109, 3749-3766.
31. Shafer, S. J.; Closson, W. D. J. Org. Chem. 1975, 40, 889-892.
32. (h) For an analogous migration of N-acylphenothiazines, see: Hallberg, A.; Svensson, A.; Martin, A. R. Tetrahedron Lett. 1986, 27, 1959-1962.
33. For an interesting migration in a thiophene 2-sulfonamide, see: Slocum, D. W.; Gierer, P. L. J. Org. Chem. 1973, 38, 4189-4192.
34. Detailed studies will be the subject of a full paper. See also: MacNeil, S. L. M.Sc. Thesis, University of Waterloo, 1997.
35. For reports on rearrangements of different N-groups, see refs 7d-h.
36. 2, 2-TMS-indole, see: Hartung, C. G.; Fecher, A.; Chapell, B.; Snieckus, V. Org. Lett. 2003, 5, 1899-1902.
37. For detailed optimization studies, see: Wilson, B. M.Sc. Thesis, Queen's University, 2004.
38. See: (a) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216.
39. For reviews, see: (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209.
40. (c) Hartwig, J. F. In Modern Arene Chemistry: Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 107-168.
41. The lack of N-deprotected products and products possessing two amide substituents, one at nitrogen and one at the ortho- or ortho′-position, which would arise by an intermolecular N → C carbamoyl migration, suggests but does not prove an intramolecular mechanism for the reaction.
42. Under LDA conditions, this compound gives 1-methoxyfluoren-9-one, the result of remote metalation-cyclization, see: Fu, J.-m.; Zhao, B.-p.; Sharp, M. J.; Snieckus, V. J. Org. Chem. 1991, 50, 1683-1685.
43. For an indication of the generality of this reaction, see ref 3.
44. For other synthetic applications, see James, C. A. Ph.D. Thesis, University of Waterloo, 1998.
45. An important example is GF120918, an acridone 1-carboxamide that has been identified as an optimized inhibitor of multidrug resistance (MDR), see: (a) Ward, K. W.; Azzarano, L. M. J. Pharmacol. Exp. Ther. 2004, 310, 703-709.
46. (b) Hyafil F.; Vergely C.; Du Vignaud P.; Grand-Perret T. Cancer Res. 1993, 53, 4595-602.
47. For a comprehensive review on the isolation, structural elucidation, synthesis, biochemistry, and biological activities of these and other naturally occurring acridones, see: Skaltsounis, A. L.; Mitaku, S.; Tillequin, F. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 2000; Vol. 54, pp 259-377.
48. (a) Takemura, Y.; Uchida, H.; Juichi, M.; Omura, M.; Ito, C.; Nakagawa, K.; Ono, T.; Furukawa, H. Heterocycles 1992, 34, 2123-2130.
49. (b) Juichi, M.; Inoue, M.; Sakiyama, K.; Yoneda, M.; Furukawa, H. Heterocycles 1987, 26, 2077-2079.
50. Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
51. LiTMP was found to yield superior results to LDA for this particular transformation. See ref 12.
52. The di-OMOM ether corresponding to 15 also led to complex product mixtures. For sensitivity of MOM derivatives to strong bases, see ref 16.
53. Charette, A. B.; Chua, P. Synlett 1998, 163.
54. Sala, T.; Sargent, M. V. J. Chem. Sec., Perkin Trans. 1 1979, 2593-2598.
55. A sample was found to be identical with the natural product by comparison of NMR and other spectroscopic and physical data. For yukodine, see ref 19a, for junosidine, see ref 19b.
56. Chauder, B. A.; Lopes, C. C.; Lopes, R. S. C.; da Silva, A. J. M.; Snieckus, V. Synthesis 1998, 279.
57. Juichi, M.; Inoue, M.; Kuniko, A.; Furukawa, H. Heterocycles 1986, 24, 1595-1597.
58. Buchwald-Hartwig conditions typically afford products in higher yields, under milder conditions, than classical Ullmann conditions. For a direct comparison involving N-phenyl-4-methoxyaniline, see: Anémian, R.; Morel, Y.; Baldeck, P. L.; Paci, B.; Kretsch, K.; Nunzi, J.-M.; Andraud, C. J. Mater. Chem. 2003, 13, 2157-2163.