Fluoride ion-induced cyclization of o-[bis(trimethylsilyl)methyl]-N-acylbenzamide derivatives. New efficient synthesis of 2,3-differentially substituted 1(2H)-isoquinolones

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1997, Pages 469-476

  Couture, Axel ^a   Cornet, Hélène ^a   Deniau, Eric ^a   Grandclaudon, Pierre ^a   Lebrun, Stéphane ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748641204     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a605077h     Document Type: Article

References (103)

1. T. Kametani, The Chemistry of the Isoquinoline Alkaloids, Hirokawa, Tokyo and Elsevier, Amsterdam, 1968;
2. S. F. Martin, The Alkaloids, ed. A. R. Brossi, Academic Press, New York, 1987, vol. XXXI, p. 252;
3. R. C. Thompson and J. Kallmerten, J. Org. Chem., 1990, 55, 6076;
4. R. D. Clark and M. Souchet, Tetrahedron Lett., 1990, 31, 193;
5. T. Kametani, The Chemistry of the Isoquinoline Alkaloids, The Sendai Institute of Heterocyclic Chemistry, Sendai, 1974, vol. 2;
6. M. Shamma, The Isoquinoline Alkaloids, Chemistry and Pharmacology, Academic Press, New York, 1972;
7. T. S. Sulkowski and M. A. Wilke, U.S. Pat., 3 452 027, 1969 (Chem. Abstr., 1969, 71, 112830);
8. W. E. Coyne and J. W. Cusic, U.S. Pat., 3 600 394, 1971 (Chem. Abstr., 1971, 75, 118241);
9. K. Kubo, N. I to, I. Sozu, Y. Isomura and H. Homma, Ger. Pat., 2 828 528, 1979 (Chem. Abstr., 1979, 90, 168468);
10. K. Kubo, N. Ito, Y. Isomura, I. Sozu, H. Homma and M. Murakami, Chem. Pharm. Bull., 1979, 27, 2372;
11. T. Wakabayashi and K. Watanabe, Jap. Pat., 78 119 879, 1979 (Chem. Abstr., 1979, 90, 152028).
12. A. Mondon, Erythrina Alkaloids, in Chemistry of the Alkaloids, ed. S. W. Pelletier, Van Nostrand, Reinhold, New York, 1970, p. 137;
13. Y. Tsuda and K. Isobe, J. Chem. Soc. D, 1971, 1555;
14. R. V. Stevens, L. E. DuPree, Jr. and P. L. Loewenstein, J. Org. Chem., 1972, 37, 977;
15. H. W. Whitlock Jr. and G. L. Smith, J. Am. Chem. Soc., 1967, 89, 3600;
16. T. Kametani and K. Fukumoto, Heterocycles, 1975, 3, 931;
17. T. Kametani, M. Kajiwara, T. Takahashi and K. Fukumoto, Heterocycles, 1975, 3, 179;
18. T. Kametani, Y. Hirai, M. Kajiwara, T. Takahashi and K. Fukumoto, Chem. Pharm. Bull., 1975, 23, 2634;
19. T. Kametani, H. Takeda, Y. Hirai, F. Satoh and K. Fukumoto, J. Chem. Soc., Perkin Trans. 1, 1974, 2141;
20. H. Irie, K. Akagi, D. Tani, K. Yabusaki and H. Yamane, Chem. Pharm. Bull., 1973, 21, 855;
21. H. Irie, J. Fukudome, T. Ohmori and J. Tanaka, J. Chem. Soc., Chem. Commun., 1975, 63;
22. W. Fleishhacker, R. Hloch and F. Viebock, Monatsh. Chem., 1968, 99, 1586;
23. G. Stork and R. N. Guthikonda, J. Am. Chem. Soc., 1972, 94, 5109.
24. (a) A. Couture, P. Grandclaudon and S. Hooijer, J. Org. Chem., 1991, 56, 4977;
25. (b) A. Couture and P. Grandclaudon, Synthesis, 1986, 576;
26. (c) A. Couture, H. Cornet and P. Grandclaudon, Tetrahedron, 1992, 48, 3857;
27. (d) A. Couture, E. Deniau, P. Grandclaudon and P. Woisel, Tetrahedron, 1996, 52, 4433.
28. I. R. Girling and D. A. Widdowson, Tetrahedron Lett., 1982, 23, 1957;
29. J. Chem. Soc., Perkin Trans. 1, 1988, 1317.
30. R. M. Letcher, N.-C. Kwok and K.-K. Cheung, J. Chem. Soc., Perkin Trans. 1, 1992, 1769.
31. (a) E. Stanoeva, M. A. Haimova and V. I. Ognyanov, Liebigs Ann. Chem., 1984, 389;
32. (b) M. A. Haimova, V. I. Ognyanov and N. M. Mollov, Synthesis, 1980, 845.
33. A. Cobas, E. Guitian and L. Castedo, J. Org. Chem., 1993, 58, 3113.
34. C. Kaneko, T. Naito and C. Miwa, Chem. Pharm. Bull., 1982, 30, 752.
35. R. Beugelmans and M. Bois-Choussy, Synthesis, 1981, 729.
36. E. Dominguez, E. Martinez de Marigorta, L. Carillo and R. Fananas, Tetrahedron, 1991, 47, 9253.
37. (a) J. R. Brooks, D. N. Harcourt and R. D. Waigh, J. Chem. Soc., Perkin Trans. 1, 1973, 2588;
38. (b) M. Haraoka, H., Yamagishi, M. Marutani and C. Mukai, Tetrahedron Lett., 1984, 25, 5169.
39. R. C. Larock, C.-L. Liu, H. H. Lau and S. Varaprath, Tetrahedron Lett., 1984, 25, 4459.
40. D. E. Korte, L. S. Hegedus and R. K. Wirth, J. Org. Chem., 1977, 42, 1329.
41. R. Singh, R. P. Singh and J. N. Srivastava, J. Indian Chem. Soc., 1991, 68, 276.
42. R. S. Mali, B. K. Kulkarnie and K. Shankaran, Synthesis, 1982, 329;
43. M. U. Koller, C. Church, C. L. Griffith, M. A. Hines, R. J. Lachicotte, R. A. Taylor and C. F. Beam, Synth. Commun., 1996, 26, 1763.
44. A. Couture, H. Cornet and P. Grandclaudon, Tetrahedron Lett., 1993, 34, 8097.
45. For an exhaustive review on lateral lithiation reactions promoted by heteroatomic substituents, see R. D. Clark and A. Jahangir, Org. React., 1995, 47, 1.
46. M. S. Hendi, K. J. Nathalie, S. B. Hendi, J. A. Campbell, T. O. Greenwood and J. F. Wolfe, Tetrahedron Lett., 1989, 30, 275.
47. (a) P. Beak and V. Snieckus, Acc. Chem. Res., 1982, 15, 306;
48. (b) V. Snieckus, Chem. Rev., 1990, 90, 879;
49. (c) Heterocycles, 1980, 14, 1679;
50. (d) Bull. Soc. Chim. Fr., 1988, 67.
51. H. W. Gschwend and H. R. Rodriguez, Org. React., 1979, 26, 1.
52. (a) G. H. Hitchings and J. M. Vernon, J. Chem. Soc., Perkin Trans. 1, 1990, 1757;
53. (b) A. A. Bahajaj and J. M. Vernon, J. Chem. Soc., Perkin Trans. 1, 1996, 1041;
54. (c) J. Epstajn, A. Jozwiak and J. A. Krysiak, Tetrahedron, 1994, 50, 2907;
55. (d) M. C. Delcey, C. Huel and E. Bisagni, Heterocycles, 1995, 41, 1721.
56. S. Nahm and S. M. Weinreb, Tetrahedron Lett., 1981, 22, 3815.
57. P. Beak, A. Tse, J. Hawkins, C.-W. Chen and S. Mills, Tetrahedron, 1983, 39, 1983.
58. J. J. Court and D. J. Hlasta, Tetrahedron Lett., 1996, 37, 1335.
59. J. S. DePue and D. B. Collum, J. Am. Chem. Soc., 1988, 110, 5524;
60. D. Barr, W. Clegg, R. E. Mulvey, R. Snaith and D. S. Wright, J. Chem. Soc., Chem. Commun., 1987, 716;
61. P. Renaud and M. A. Fox, J. Am. Chem. Soc., 1988, 110, 5702;
62. M. Newcomb, M. T. Burchill and T. M. Deeb, J. Am. Chem. Soc., 1988, 110, 6528;
63. R. R. Fraser and T. S. Mansour, J. Org. Chem., 1984, 49, 3442.
64. T. D. Krisan and J. C. Martin, J. Am. Chem. Soc., 1983, 105, 6155;
65. E. J. Corey and A. W. Gross, Tetrahedron Lett., 1984, 25, 495;
66. P. E. Eaton, C.-H. Lee and Y. Xiong, J. Am. Chem. Soc., 1989, 111, 8016.
67. For reviews of the Peterson reaction, see, (a) D. J. Ager, Org. React., 1990,3 8, 1;
68. (b) D. J. Ager, Synthesis, 1984, 384;
69. W. P. Weber, Silicon Reagents for Organic Synthesis, Springer-Verlag, Berlin, 1983, p. 58;
70. S. B. Rutschmann, Schweiz. Lab. Z., 1983, 40, 270
71. (Chem. Abstr., 1984, 100, 68332).
72. T. H. Chan, Acc. Chem. Res., 1977, 10, 442.
73. W. H. Puterbaugh and C. R. Hauser, J. Org. Chem., 1964, 29, 853;
74. M. P. Sibi, M. A. Miah and V. Snieckus, J. Org. Chem., 1984, 49, 737.
75. H. Wetter, Helv. Chim. Acta, 1978, 61, 3072;
76. S. Shimizu and M. Ogata, J. Org. Chem., 1987, 52, 2314;
77. T. Hirao, A. Yamada, Y. Ohshiro and T. Agawa, Angew. Chem., Int. Ed. Engl., 1981, 20, 126;
78. T. Hirao, A. Yamada, K. Hayashi, Y. Ohshiro and T. Agawa, Bull. Chem. Soc. Jpn., 1982, 55, 1163.
79. C. Palomo, J. M. Aizpurua, J. M. Garcia, I. Ganboa, F. P. Cossio, B. Lecea and C. Lopez, J. Org. Chem., 1990, 55, 2498;
80. J. C. Cuevas, P. Patil and V. Snieckus, Tetrahedron Lett., 1989, 30, 5841;
81. C. Palomo, J. M. Aizpurua, M. Legido, J. P. Picard, J. Dunogues and T. Constantieux, Tetrahedron Lett., 1992, 33, 5841;
82. C. Palomo, J. M. Aizpurua, J. M. Garcia, J. P. Picard and J. Dunogues, Tetrahedron Lett., 1990, 31, 1921.
83. N. M. Sazonova, I. I. Levina, V. I. Sladkov and N. N. Suvorov, Zh. Org. Chim., 1991, 9, 1979
84. (Chem. Abstr., 1991, 115, 183640);
85. M. Hanaoka, T. Motonoshi and C. Mukai, J. Chem. Soc., Chem. Commun., 1984, 718;
86. R. Beugelmans and M. Bois-Choussy, Tetrahedron, 1992, 48, 8285.
87. K. Kubo, N. Ito, I. Sozu, Y. Isomura and H. Homma, Jap. Pat. 79 163 585, 1979 (Chem. Abstr., 1980, 93, 8037).
88. M. Reuman and A. I. Meyers, Tetrahedron, 1985, 41, 837.
89. A. Couture, H. Cornet and P. Grandclaudon, J. Organomet. Chem., 1992, 440, 7.
90. B. L. Chenard, C. Slapak, D. K. Anderson and J. S. Swenton, J. Chem. Soc., Chem. Commun., 1981, 179.
91. I. E. Marko and A. Mekhalfia, Tetrahedron Lett., 1990, 31, 7237.
92. M. Hojo, M. Ohkuma, N. Ishibashi and A. Hosomi, Tetrahedron Lett., 1993, 34, 5943.
93. W. J. Middleton, Org. Synth., 1986, 64, 221;
94. W. J. Middleton and C. F. Pa, U.S. Pat. 3 940402, 1976 (Chem. Abstr., 1976, 85, 6388);
95. R. Noyori, I. Nishida and J. Sakuta, J. Am. Chem. Soc., 1983, 105, 1598.
96. C. L. Liotta and H. P. Harris, J. Am. Chem. Soc., 1974, 96, 2250;
97. J. P. Marino and E. Laborde, J. Org. Chem., 1987, 52, 1.
98. D. P. Cox, J. Terpinski and W. Lawrynowicz, J. Org. Chem., 1984, 49, 3216.
99. G. Bartoli, G. Palmieri, M. Petrini, M. Bosco and R. Dalpozzo, Tetrahedron, 1990, 46, 1379.
100. A. R. Bassindale and P. G. Taylor, in The Chemistry of Organic Silicon Compounds, Part 1, ed. S. Patai and Z. Rappoport, Wiley, New York, 1989, p. 839.
101. L. Duhamel and J. C. Plaquevent, J. Organomet. Chem., 1993, 448, 1.
102. A. I. Meyers, D. L. Temple, D. Haidukewych and E. D. Mihelich, J. Org. Chem., 1974, 39, 2787.
103. L. Kronber and B. Danielson, Acta Pharm. Suec., 1971, 8, 373.