New synthetic applications of aryllead triacetates. N-arylation of amides

Journal of Organic Chemistry

Volumn 61, Issue 17, 1996, Pages 5865-5870

  López Alvarado, Pilar ^a   Avendaño, Carmen ^a   Menéndez, J Carlos ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042181600     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960566z     Document Type: Article

References (81)

1. Dostert, P.; Strolin Benedetti, M.; Guffroy, C. J. Pharm. Pharmacol. 1983, 35, 161.
2. Scudi, J. V.; Reisner, D. B.; Childress, S. J. U.S. Pat., 2,947,754 1960. Chem. Abstr. 1961, 55, 11440d.
3. Hofmann, H. P.; Kreiskott, H.; Kretzchmar, R. NaunynSchmiedeberg's Arch. Pharmacol. 1982, 32 (Suppl.), R44.
4. Campbell, A.; Martin, M. K.; Farrington, K. J.; Erdelyi, A.; Johnston, R.; Sorby, P.; Whitlock, H. V.; Pearson, I. G.; Jones, R. C.; Haigh, J. A.; DeGoosh, C. P. Experientia 1967, 23, 992.
5. Presidente, P. J. A.; Knapp, S. E.; Schlegel, M. W.; Armstrong, J. N. Am. J. Vet. Res. 1972, 33, 1593.
6. Examples: (a) Sen, A. B.; Sen Gupta, A. K. J. Indian Chem. Soc. 1957, 34, 413. (b) Nodiff, E. A.; Lipschutz, S.; Craig, P. N.; Gordon, M. J. Org. Chem. 1960, 25, 60. (c) Thu-Cuc, T.; Buu-Hoi, N. P.; Xuong, N. D. J. Heterocycl. Chem. 1964, 1, 28.
7. Examples: (a) Sen, A. B.; Sen Gupta, A. K. J. Indian Chem. Soc. 1957, 34, 413. (b) Nodiff, E. A.; Lipschutz, S.; Craig, P. N.; Gordon, M. J. Org. Chem. 1960, 25, 60. (c) Thu-Cuc, T.; Buu-Hoi, N. P.; Xuong, N. D. J. Heterocycl. Chem. 1964, 1, 28.
8. Examples: (a) Sen, A. B.; Sen Gupta, A. K. J. Indian Chem. Soc. 1957, 34, 413. (b) Nodiff, E. A.; Lipschutz, S.; Craig, P. N.; Gordon, M. J. Org. Chem. 1960, 25, 60. (c) Thu-Cuc, T.; Buu-Hoi, N. P.; Xuong, N. D. J. Heterocycl. Chem. 1964, 1, 28.
9. Examples: (a) Tanaka, S.; Seguchi, K.; Itoh, K.; Sera, A. J. Chem. Soc., Perkin Trans. 1 1994, 2335. (b) Tanaka, S.; Seguchi, K.; Itoh, K.; Sera, A. Chem. Lett. 1994, 771. (c) Tanaka, S.; Seguchi, K.; Sera, A. Heterocycles 1994, 38, 2581. (d) Tanaka, S.; Seguchi, K.; Sera, A. J. Chem. Soc., Perkin Trans. 1 1995, 519.
10. Examples: (a) Tanaka, S.; Seguchi, K.; Itoh, K.; Sera, A. J. Chem. Soc., Perkin Trans. 1 1994, 2335. (b) Tanaka, S.; Seguchi, K.; Itoh, K.; Sera, A. Chem. Lett. 1994, 771. (c) Tanaka, S.; Seguchi, K.; Sera, A. Heterocycles 1994, 38, 2581. (d) Tanaka, S.; Seguchi, K.; Sera, A. J. Chem. Soc., Perkin Trans. 1 1995, 519.
11. Examples: (a) Tanaka, S.; Seguchi, K.; Itoh, K.; Sera, A. J. Chem. Soc., Perkin Trans. 1 1994, 2335. (b) Tanaka, S.; Seguchi, K.; Itoh, K.; Sera, A. Chem. Lett. 1994, 771. (c) Tanaka, S.; Seguchi, K.; Sera, A. Heterocycles 1994, 38, 2581. (d) Tanaka, S.; Seguchi, K.; Sera, A. J. Chem. Soc., Perkin Trans. 1 1995, 519.
12. Examples: (a) Tanaka, S.; Seguchi, K.; Itoh, K.; Sera, A. J. Chem. Soc., Perkin Trans. 1 1994, 2335. (b) Tanaka, S.; Seguchi, K.; Itoh, K.; Sera, A. Chem. Lett. 1994, 771. (c) Tanaka, S.; Seguchi, K.; Sera, A. Heterocycles 1994, 38, 2581. (d) Tanaka, S.; Seguchi, K.; Sera, A. J. Chem. Soc., Perkin Trans. 1 1995, 519.
13. (a) Freeman, H. S.; Butler, J. R.; Freeman, L. D. J. Org. Chem. 1978, 43, 4975.
14. (b) Yamamoto, T.; Kurata, Y. Chem. Ind. (London) 1981, 737.
15. (c) Greiner, A. Synthesis 1981, 472.
16. (a) Fanta, P. E. Chem. Rev. 1964, 64, 613.
17. (b) Yamamoto, T.; Kurata, Y. Can. J. Chem. 1983, 61, 86.
18. (c) Lindley, J. Tetrahedron 1984, 40, 1433.
19. (a) Bacon, R. G. R.; Karin, A. J. Chem. Soc., Perkin Trans. 1 1973, 272.
20. (b) Sato, M.; Ebine, S. Synthesis 1981, 472.
21. Seuron, P.; Varrailon, D. Eur. Pat. Appl. EP 436,426 (July 10, 1991). Chem. Abstr., 1991, 115, P159140k.
22. Coutts, I. G. C.; Hamblin, M. J. Chem. Soc., Perkin Trans. 1 1975, 2445.
23. Greiner, A., Synthesis 1989, 312.
24. (a) Beringer, F. M.; Brierley, A.; Drexler, M.; Gindler, E. M.; Lumpkin, C. C. J. Am. Chem. Soc. 1953, 75, 2708-2712.
25. (b) Nesmeyanov, A. N.; Makarova, L. G.; Tolstaya, T. P. Tetrahedron 1957, 1, 145-157.
26. Reviews: (a) Varvoglis, A. Synthesis 1984, 709. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Prakash, O.; Singh, S. P. Aldrichim. Acta 1994, 27, 15.
27. Reviews: (a) Varvoglis, A. Synthesis 1984, 709. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Prakash, O.; Singh, S. P. Aldrichim. Acta 1994, 27, 15.
28. Reviews: (a) Varvoglis, A. Synthesis 1984, 709. (b) Moriarty, R. M.; Vaid, R. K. Synthesis 1990, 431. (c) Prakash, O.; Singh, S. P. Aldrichim. Acta 1994, 27, 15.
29. Schoemberg, A.; Heck, R. F. J. Org. Chem. 1974, 39, 3327.
30. For a review of the more recent arylation methods, see: Abramovitch, R. A.; Barton, D. H. R.; Finet, J.-P. Tetrahedron 1988, 44, 3039.
31. For reviews of several aspects of palladium-catalyzed cross-coupling reactions including arylation, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47. (c) Kalinia, V. N. Synthesis 1992, 413.
32. For reviews of several aspects of palladium-catalyzed cross-coupling reactions including arylation, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47. (c) Kalinia, V. N. Synthesis 1992, 413.
33. For reviews of several aspects of palladium-catalyzed cross-coupling reactions including arylation, see: (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508. (b) Scott, W. J.; McMurry, J. E. Acc. Chem. Res. 1988, 21, 47. (c) Kalinia, V. N. Synthesis 1992, 413.
34. Finet, J.-P. Chem. Rev. 1989, 89, 1457.
35. Pinhey, T. J. Aust. J. Chem. 1991, 44, 1353.
36. For the synthesis of aryllead triacetates, see reference 20 and: (a) Vos, D. de; Wolters, J.; Van der Gen, A. J. Organomet. Chem. 1972, 39, C61. (b) Bell, H. C.; Kalman, J. R.; Pinhey, J. T.; Sternhell, S. Aust. J. Chem. 1979, 32, 1521. (c) Kozyrod, R. P.; Morgan, J.; Pinhey, J. T. Aust. J. Chem. 1985, 38, 1155. (d) Morgan, J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1990, 715.
37. For the synthesis of aryllead triacetates, see reference 20 and: (a) Vos, D. de; Wolters, J.; Van der Gen, A. J. Organomet. Chem. 1972, 39, C61. (b) Bell, H. C.; Kalman, J. R.; Pinhey, J. T.; Sternhell, S. Aust. J. Chem. 1979, 32, 1521. (c) Kozyrod, R. P.; Morgan, J.; Pinhey, J. T. Aust. J. Chem. 1985, 38, 1155. (d) Morgan, J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1990, 715.
38. For the synthesis of aryllead triacetates, see reference 20 and: (a) Vos, D. de; Wolters, J.; Van der Gen, A. J. Organomet. Chem. 1972, 39, C61. (b) Bell, H. C.; Kalman, J. R.; Pinhey, J. T.; Sternhell, S. Aust. J. Chem. 1979, 32, 1521. (c) Kozyrod, R. P.; Morgan, J.; Pinhey, J. T. Aust. J. Chem. 1985, 38, 1155. (d) Morgan, J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1990, 715.
39. For the synthesis of aryllead triacetates, see reference 20 and: (a) Vos, D. de; Wolters, J.; Van der Gen, A. J. Organomet. Chem. 1972, 39, C61. (b) Bell, H. C.; Kalman, J. R.; Pinhey, J. T.; Sternhell, S. Aust. J. Chem. 1979, 32, 1521. (c) Kozyrod, R. P.; Morgan, J.; Pinhey, J. T. Aust. J. Chem. 1985, 38, 1155. (d) Morgan, J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1990, 715.
40. May, G. L.; Pinhey, J. T. Aust. J. Chem. 1982, 35, 1859.
41. (a) Kozyrod, R. P.; Pinhey, J. T. Aust. J. Chem. 1985, 38, 713.
42. (b) Morgan, J.; Pinhey, J. T. J. Chem. Soc. Perkin Trans 1 1993, 1673.
43. (c) Barton, D. H. R.; Donnelly, D. M. X.; Guiry, P. J.; Finet, J. P. J. Chem. Soc., Perkin Trans. 1 1994, 2921.
44. Morgan, J.; Buys, I.; Hambley, T. W.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1993, 1677.
45. Bell, H. C.; Pinhey, J. T.; Sternhell, S. Aust. J. Chem. 1979, 32, 1551.
46. (a) Pinhey, J. T.; Rowe, B. A. Aust. J. Chem. 1979, 32, 1561.
47. (b) Kozyrod, R. P.; Morgan, J.; Pinhey, J. T. Aust. J. Chem. 1985, 38, 1155.
48. (c) Orito, K.; Yorita, K.; Suginome, H. Tetrahedron Lett. 1991, 32, 5999,
49. (d) Donnelly, D. M. X.; Finet, J. P.; Rattigan, B. A. J. Chem. Soc., Perkin Trans. 1 1993, 1729.
50. (a) Kozyrod, R. P.; Morgan, J.; Pinhey, J. T. Aust. J. Chem. 1991, 44, 369.
51. (b) Parkinson, C. J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1991, 1503.
52. (c) Koen, M. J.; Morgan, J.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1993, 2583.
53. (d) Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J.; Hutchinson, R. M. J. Chem. Soc., Perkin Trans. 1 1990, 2851.
54. (e) Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J. Tetrahedron Lett. 1989, 30, 1539.
55. (f) Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J. Tetrahedron Lett. 1990, 31, 7449.
56. (g) Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J.; Kielty, J. M. Tetrahedron Lett. 1990, 31, 6637.
57. (h) Donnelly, D. M. X.; Finet, J.-P.; Kielty, J. M. Tetrahedron Lett. 1991, 32, 3835.
58. (i) Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J. J. Chem. Soc., Perkin Trans. 1 1992, 1365.
59. (j) Donnelly, D. M. X.; Kielty, J. M.; Cormons, A.; Finet, J.-P. J. Chem. Soc., Perkin Trans. 1 1993, 2069.
60. (k) Donnelly, D. M. X.; Fitzpatrick, B. M.; Finet, J.-P. J. Chem. Soc., Perkin Trans. 1 1994, 1791.
61. (l) Donnelly, D. M. X.; Fitzpatrick, B. M.; Ryan, S. M.; Finet, J.-P. J. Chem. Soc., Perkin Trans. 1 1994, 1797.
62. Huber, M.-L.; Pinhey, J. T. J. Chem. Soc., Perkin Trans. 1 1990, 721.
63. Barton, D. H. R.; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1986, 27, 3615.
64. (a) Barton, D. H. R.; Yadav-Bhatnagar, N. ; Finet, J.-P.; Khamsi, J. Tetrahedron Lett. 1987, 27, 3111.
65. (b) Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J. Tetrahedron Lett. 1989, 30, 1377.
66. (c) Barton, D. H. R.; Donnelly, D. M. X.; Finet, J.-P.; Guiry, P. J. J. Chem. Soc., Perkin Trans. 1 1991, 2095.
67. (a) López-Alvarado, P.; Avendaño, C.; Menéndez, J. C. Tetrahedron Lett. 1992, 33, 659.
68. (b) López-Alvarado, P.; Avendaño, C.; Menéndez, J. C. J. Org. Chem., 1995, 60, 5678.
69. Preliminary communication: López-Alvarado, P.; Avendaño, C.; Menéndez, J. C. Tetrahedron Lett. 1992, 33, 6875.
70. 3 was essential in order to ensure solubilization of the aryllead reagent.
71. 3, 250 MHz) δ7.79 (d, 2H, J = 8.1 Hz); 7.41 (d, 2H, J = 7.9 Hz.); 7.01 (d, 2H, J = 8.4 Hz); 6.95 (br s, IH); 671 (d, 2H, J = 8.4 Hz); 4.85 (br s, 2H); 2.39 (s, 3H) ppm.
72. Gesto, C.; de la Cuesta, E.; Avendaño, C. Synthesis 1991, 727.
73. Taneja, A. D.; Rao, N. U. M.; Tiwari, H. P.; Prasad, C. S. G. J. Inorg. Nucl. Chem. 1974, 36, 2039.
74. Clemens, R. J.; Hyatt, J. A. J. Org. Chem. 1985, 50, 2431. For a review of the chemistry of 1,3-dioxin-4-ones, see: Sato, M. Yakugaku Zasshi 1988, 108, 805.
75. Clemens, R. J.; Hyatt, J. A. J. Org. Chem. 1985, 50, 2431. For a review of the chemistry of 1,3-dioxin-4-ones, see: Sato, M. Yakugaku Zasshi 1988, 108, 805.
76. The main degradation pathway previously known for β-ketoanilides was photochemical decomposition to ketones and aryl isocyanates. See: (a) Mukaiyama, T.; Tozikawa, M.; Nohira, H.; Takai, H. J. Org. Chem. 1961, 26, 4381. (b) Reisch, J.; Niemeyer, D. Tetrahedron 1971, 27, 4637. (c) Fahmy, A. F. M.; Badday, H. A.; Alkhateeb, A. N. Indian J. Chem. Sect. B 1981, 20B, 489.
77. The main degradation pathway previously known for β-ketoanilides was photochemical decomposition to ketones and aryl isocyanates. See: (a) Mukaiyama, T.; Tozikawa, M.; Nohira, H.; Takai, H. J. Org. Chem. 1961, 26, 4381. (b) Reisch, J.; Niemeyer, D. Tetrahedron 1971, 27, 4637. (c) Fahmy, A. F. M.; Badday, H. A.; Alkhateeb, A. N. Indian J. Chem. Sect. B 1981, 20B, 489.
78. The main degradation pathway previously known for β-ketoanilides was photochemical decomposition to ketones and aryl isocyanates. See: (a) Mukaiyama, T.; Tozikawa, M.; Nohira, H.; Takai, H. J. Org. Chem. 1961, 26, 4381. (b) Reisch, J.; Niemeyer, D. Tetrahedron 1971, 27, 4637. (c) Fahmy, A. F. M.; Badday, H. A.; Alkhateeb, A. N. Indian J. Chem. Sect. B 1981, 20B, 489.
79. Compounds very similar to 15, but existing as dioxo tautomers, are stable in solution. P. López-Alvarado, Ph. D. Thesis. Universidad Complutense, Madrid, 1995.
80. Jones, A. B. In Comprenhensive Organic Synthesis; Ley, S. V., Ed.; Trost, B. M., Fleming, I., Gen Eds.; Pergamon Press: New York, 1991; Vol. 7, p 151.
81. This enol content corresponds to a freshly prepared solution and quickly rose to 67% before decomposition to 16a.