A short and efficient synthesis of 3-diphenylphosphoryl- and 3-diethoxyphosphoryl(aza)isoindolinones: Extension to the sulfonylated analogs

Synthesis

Volumn , Issue 12, 1997, Pages 1439-1445

  Couture, Axel ^a   Deniau, Eric ^a   Woisel, Patrice ^a   Grandclaudon, Pierre ^a  

^a CNRS   (France)

Author keywords

Aryne mediated cyclization; Phosphorylated and sulfonylated (aza)isoindolinones; Phosphorylated amino carbanions

Indexed keywords

3 DIETHOXYPHOSPHORYL(AZA)ISOINDOLINONE; 3 DIPHENYLPHOSPHORYLISOINDOLINONE; AMIDE; BENZAMIDE DERIVATIVE; PHOSPHORAMIDIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; NONHUMAN; SYNTHESIS;

EID: 0031468005     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1370     Document Type: Article

References (89)

1. Kafarski, P.; Lejczak, B. Phosphorus, Sulfur, Silicon 1991, 63, 193.
2. Kafarski, P.; Lejczak, B.; Mastalerz, P. Phosphonopeptides, Synthesis and Biological Activity; Beiträge zur Wirkstofforschung, Ak. Ind. Kompl. DDR 1985; Vol. 25 and references cited therein.
3. Dahwan, B.; Redmore, D. Phosphorus, Sulfur, Silicon 1987, 132, 119.
4. Petrillo, E.W.; Spitzmiller, E.R. Tetrahedron Lett. 1979, 4929.
5. Gruszecka, E.; Sokora, M.; Mastalerz, P. Pol. J. Chem. 1979, 53, 75.
6. Issleib, K. Nachr. Chem. Tech. 1987, 35, 1037.
7. Jacobsen, N.E.; Bartlett, P.A. J. Am. Chem. Soc. 1981, 103, 654.
8. Hoagland, R.E. In Biological Active Natural Products; Culter, H. G., Ed.; Symposium Series 380; American Chemical Society: Washington DC, 1968; p 182.
9. Hoppe, I.; Schöllkopf, U.; Nieger, M.; Egert, E. Angew. Chem., Int. Ed. Engl. 1985, 14, 1067.
10. Schrader, T.; Kober, R.; Steglich, W. Synthesis 1986, 372.
11. Huber, R.; Vasella, A. Helv. Chim. Acta 1987, 70, 1461.
12. Jacquier, R.; Ouazzani, F.; Roumestant, M.-L.; Viallefont, P. Phosphorus, Sulfur, Silicon 1988, 36, 73.
13. Sawamura, M.; Ito, Y.; Hayashi, T. Tetrahedron Lett. 1989, 30, 2247.
14. Hanessian, S.; Bennani, Y.L. Tetrahedron Lett. 1990, 31, 6465.
15. Sting, M.; Steglich, W. Synthesis 1990, 132.
16. von der Saal, W.; Leinert, H.; Boehm, E. Ger. Offen. DE 3925584, 1990; Chem. Abstr. 1991, 115, 29627.
17. Stauffer Co (Large, G.B.) U.S. Patent 4170463, 1979; Chem. Abstr. 1980, 92, 164085.
18. Emsley, J.; Hall, D. The Chemistry of Phosphorus; Harper and Row: London, 1976.
19. Lukanov, L.K.; Venkov, A.P. Synthesis 1992, 263.
20. Fields, E.K. J. Am. Chem. Soc. 1952, 74, 1528.
21. Moedritzer, K.; Irani, R.R. J. Org. Chem. 1966, 31, 1603.
22. Huber, J.W., III; Middlebrooks, M. Synthesis 1977, 883.
23. Oleksyszyn, J.; Subotkowska, L.; Mastalerz, P. Synthesis 1979, 985.
24. Lejczak, B.; Kafarski, P.; Soroka, M.; Mastalerz, P. Synthesis 1984, 577.
25. Tam, C.C.; Mattocks, K.; Tishler, M. Synthesis 1982, 188.
26. Baraldi, P.G.; Guarneri, M.; Moroder, F.; Pollini, G.P.; Simoni, O. Synthesis 1982, 653.
27. Yuan, C.; Chen, S. Synthesis 1992, 1124.
28. Schrader, T.; Steglich, W. Synthesis 1989, 97.
29. Möhrle, H.; Vetter, W. Z. Naturforsch. 1988, 43b, 1662.
30. Shono, T.; Matsumura, Y.; Kanasawa, T. Tetrahedron Lett. 1983, 24, 4577.
31. Satoh, H.; Tsuji, T. Tetrahedron Lett. 1984, 25, 1733.
32. Campbell, M.M.; Carruthers, N.I.; Mickel, S.J. Tetrahedron 1982, 38, 2513.
33. Katritzky, A.R.; Wu, H.; Xie, L. Synth. Commun. 1995, 25, 1187.
34. Couture, A.; Deniau, E.; Grandclaudon, P. Synthesis 1994, 953.
35. Takahashi, I.; Kawakami, T.; Hirano, E.; Yokota, H.; Kitajima, H. Synlett 1996, 353 and references cited therein.
36. Epsztajn, J.; Crzelak, R.; Jozwiak, A. Synthesis 1996, 1212.
37. Goto, T.; Utsunimiya, S.; Aiba, H.; Hayasaka, H.; Endo, M.; Watanabe, R.; Ishizaki, T.; Sato, R.; Saito, M. Bull. Chem. Soc. Jpn 1991, 64, 1901 and references cited therein.
38. Shono, T.; Matsumura, Y.; Tsukaba, K. Tetrahedron Lett. 1981, 22, 3249.
39. Failla, S.; Finocchiaro, P. Phosphorus, Sulfur, Silicon 1995, 105, 195.
40. Neidlein, R.; Greulich, P.; Kramer, W. Helv. Chim. Acta 1993, 76, 2407.
41. Corcoran, R.C.; Green, J.M. Tetrahedron Lett. 1990, 31, 6827.
42. Mali, S.; Yeola, S.N. Synthesis 1986, 755.
43. Epsztajn, J.; Jozwiak, A.; Szczesniak, A.K. Tetrahedron 1993, 49, 929.
44. Cambie, R.C.; Janssen, S.J.; Rutledge, P.S.; Woodgate, P.D. J. Organomet. Chem. 1991, 3, 387.
45. Epsztajn, J.; Jozwiak, A.; Czech, K.; Szczesniak, A.K. Monatsh. Chem. 1990, 121, 909.
46. Epsztajn, J.; Jozwiak, A.; Krysiak, J. Tetrahedron 1994, 50, 2907.
47. Epsztajn, J.; Jozwiak, A.; Szczesniak, A.K. Synth. Commun. 1994, 24, 1789.
48. Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306.
49. Snieckus, V. Chem. Rev. 1990, 90, 879.
50. Gschwend, H.W.; Rodriguez, H.R. Org. React. 1979, 26, 1.
51. Horii, Z.I.; Iwata, C.; Tamura, Y. J. Org. Chem. 1961, 26, 2273.
52. Hubert, J.C.; Wynberg, P.A.; Speckamp, W.N. Tetrahedron 1975, 31, 1437.
53. Huisgen, R.; Sauer, J. Angew. Chem. 1960, 72, 91.
54. Huisgen, R.; König, H.; Lepley, A. Chem. Ber. 1960, 93, 1496.
55. Bunnett, J.F.; Hrutfiord, B.F. J. Am. Chem. Soc. 1958, 80, 2021 and 4745.
56. Bunnett, J.F.; Skorcz, J.A. J. Org. Chem. 1962, 27, 3836.
57. Bunnett, J.F.; Kato, T.; Flynn, R.R.; Skorcz, J.A. J. Org. Chem. 1963, 28, 1.
58. Kessar, V.S. Acc. Chem. Res. 1978, 11, 283.
59. Caubere, C.; Caubere, P.; Ianelli, S.; Nardelli, M.; Jamart-Gregoire, B. Tetrahedron 1994, 50, 11903.
60. Jaques, B.; Wallace, R.G. J. Chem. Soc., Chem. Commun. 1972, 397.
61. For reviews see: Beak, P.; Reitz, D.B. Chem. Rev. 1978, 78, 275.
62. Beak, P.; Zajdel, W.J.; Reitz, D.B. Chem. Rev. 1984, 84, 471.
63. Meyers, A.I. Aldrichimica Acta 1985, 18, 59.
64. Gawley, P.E.; Rein, K.S. In Comprehensive Organic Synthesis; Trost, B.M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 1, Chapter 2.1 and Vol. 3, Chapter 1.2.
65. Couture, A.; Deniau, E.; Grandclaudon, P. Tetrahedron Lett. 1993, 34, 1479.
66. Bakker, B.H.; Tjin A-Lim, D.S.; van der Gen, A. Tetrahedron Lett. 1984, 25, 4259.
67. Couture, A.; Deniau, E.; Grandclaudon, P.; Woisel, P. Tetrahedron Lett. 1996, 37, 3697.
68. Couture, A.; Deniau, E.; Grandclaudon, P.; Woisel, P. Tetrahedron 1996, 52, 4433.
69. Johnson, A.W.; Kaska, W.C.; Starzewski, K.A.O.; Dixon, D. Ylides and Imines of Phosphorus; Wiley: New York, 1993; pp 337 and 375.
70. Clayden J.; Warren, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 241.
71. Couture, A.; Deniau, E.; Gimbert, Y.; Grandclaudon, P. Tetrahedron 1993, 49, 1431.
72. Dehnel, A.; Finet, J.P.; Lavielle, G. Synthesis 1977, 474.
73. Dehnel, A.; Lavielle, G. Bull. Soc. Chim. Fr. 1978, 95.
74. Genêt, J.P.; Uziel, J.; Juge, S. Tetrahedron Lett. 1988, 29, 4559.
75. Genêt, J.P.; Uziel, J.; Touzin, A.M.; Juge, S. Synthesis 1990, 41.
76. Genêt, J.P.; Uziel, J.; Port, M.; Touzin, A.M.; Roland, S.; Thorimbert, S.; Tanier, S. Tetrahedron Lett. 1992, 33, 77.
77. Couture, A.; Deniau, E.; Woisel, P.; Grandclaudon, P. Tetrahedron Lett. 1995, 36, 2483.
78. Marko, I.E.; Mekkalfia, A. Tetrahedron Lett. 1990, 31, 7237.
79. Kessar, S.V. In Comprehensive Organic Synthesis; Trost, B.M.; Flemming, I., Eds.; Pergamon: Oxford, 1991; Vol. 4, Chapter 2.3.
80. Jung, M.E.; Lowen, G.T. Tetrahedron Lett. 1986, 27, 5319.
81. Kessar, S.V.; Gupta, Y.P.; Balakrishnan, P.; Sawal, K.K.; Mohammad, T.; Dutt, M. J. Org. Chem. 1988, 53, 1708.
82. Khanpure, S.P.; Crenshaw, L.C.; Reddy, R.T.; Biehl, E.R. J. Org. Chem. 1988, 53, 4915.
83. Olofson, R.A.; Dougherty, C.M. J. Am. Chem. Soc. 1973, 95, 582.
84. Shepard, K.L. Tetrahedron Lett. 1975, 3371.
85. Kametani, T.; Hirai, Y.; Kajiwara, M.; Takahashi, T.; Fukumoto, K. Chem. Pharm. Bull. 1975, 23, 2634.
86. Saito, S.; Miyazawa, K.; Inukai, T.; Inoue, H.; Ohno, K. EP 251,335, 1988; Chem. Abstr. 1988, 108, 177380.
87. Yamaguchi, S.; Yoschida, M.; Miyajima, I.; Araki, T.; Hirai, Y. J. Heterocycl. Chem. 1995, 32, 1517.
88. Horne, S.; Rodrigo, R. J. Org. Chem. 1990, 55, 4520.
89. Fox, H.H.; Gibas, J.T. J. Org. Chem. 1958, 23, 64.