Palladium-catalysed heteroannulation with terminal alkynes: Synthesis of phthalides

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 3, 1998, Pages 561-568

  Kundu, Nitya G ^a   Pal, Manojit ^a   Nandi, Bidisha ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

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Indexed keywords

EID: 33748651297     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a705450e     Document Type: Article

References (95)

1. A preliminary account has appeared: N. G. Kundu and M. Pal, J. Chem. Soc., Chem. Commun., 1993, 86.
2. T. Noguchi, S. Fujita and M. Kawanami, J. Pharm. Soc. Jpn., 1937, 57, 196
3. (Chem. Abstr., 1938,32, 3360).
4. J. Tang, Y. Zhang, T. G. Hartman, R. T. Rosen and C. T. Ho, J. Agric. Food Chem., 1990, 38, 1937.
5. H. J. Gold and C. W. Wilson, III, J. Org. Chem., 1963, 28, 985.
6. F. Bindler and P. Laugel, Lebensn-Wiss. Technol., 1986, 19, 369
7. (Chem. Abstr., 1987, 106, 194683a).
8. F. Van Wassenhove, P. Dirinck, G. Vulsteke and N. Schamp, Hort. Sci., 1990, 25, 556.
9. W. Pushan, G. Xuangliag, W. Yixiong, Y. Fukuyama, I. Miura and M. Sugawara, Phytochemistry, 1984, 23, 2033.
10. S. Y. Lee, M. J. Kim, D. S. Yim, H. J. Chi and H. S. Kim, Saengyak Hakhoechi (Korean), 1990, 21, 69
11. (Chem. Abstr., 1990, 113, 217923q).
12. R. H. F. Manske, Can. J. Res., 1938, 8, 142.
13. W. C. Ko, L. C. Lin, S. H. Lin, P. Y. Hwang, C. Y. Hsu, G. Y. Wang and C. W. Chang, Taiwan Yao Hsueh Tsa Chih, 1983, 35, 155
14. (Chem. Abstr., 1984, 101, 48511y).
15. M. Lacova, Czech. Pat., 257 137, 1986
16. (Chem. Abstr., 1989, 111, 115015m).
17. J. Fuska, A. Fuskova, B. Proksa, Zb. Pr. Chemickotechnol Fak. SVST, 1979-1981 (pub. 1986), 285
18. (Chem. Abstr., 1987, 106, 95582k).
19. P. Hrnciar and V. Kovalcik, Chem. Zvesti, 1962, 16, 96, 200
20. (Chem. Abstr., 1963, 59, 2731b).
21. T. G. Sinay, Jr. and R. J. Sysko, Euro. Pat., 331 314, 1989
22. (Chem. Abstr., 1990, 112, 77211h).
23. I. Cerskus and R. B. Philip, Agents Actions, 1981, 11, 281.
24. K. Kubota, Y. Ogawa, K. Hosaka and M. Chin, Jpn. Kokai Tokkyo Koho, JP01, 50 818 [8950, 818]
25. (Chem. Abstr., 1990, 112, 76923e).
26. N. E. Cundasawmy and D. B. McLean, Can. J. Chem., 1972, 50, 3028.
27. V. Scartoni, R. Fiaschi, S. Catalano, I. Morelli and A. Marsili, J. Chem. Soc., Perkin Trans. 1, 1979, 1547.
28. M. J. Broadhurst and C. H. Hassall, J. Chem. Soc., Perkin Trans. 1, 1982, 2227.
29. R. H. Prager, J. M. Tipett and A. D. Ward, Aust. J. Chem., 1981, 34, 1085;
30. S. I. Clarke, B. Kusum, R. H. Prager and A. D. Ward, Aust. J. Chem., 1983, 36, 2493.
31. M. A. Bates, P. G. Sammes and G. A. Thomson, J. Chem. Soc., Perkin Trans. 1, 1988, 3037.
32. (a) S. Gabriel, Ber. Dtsch. Chem. Ges., 1986, 19, 838;
33. S. Gabriel, Ber. Dtsch. Chem. Ges., 1893, 26, 952;
34. (b) R. Weiss, Org. Synth., 1943, 2, 61;
35. (c) G. Berti, Gazz. Chim. Ital., 1956, 86, 656;
36. (d) Z. J. Vejdelek, O. Newmecek, V. Musil and A. Simek, Collect. Czech. Chem. Commun., 1964, 29, 776.
37. J. Rigaudy and P. Derible, Bull. Soc. Chim. Fr., 1965, 3047.
38. (a) R. L. Shriner and L. S. Keyser, J. Org. Chem., 1940, 5, 200;
39. (b) E. D. Bergmann, J. Org. Chem., 1956, 21, 461.
40. S. L. Shapiro, K. Geiger and L. Freedman, J. Org. Chem., 1960, 25, 1860;
41. S. L. Shapiro, K. Geiger, J. Youlus and L. Freedman, J. Org. Chem., 1961, 26, 3580.
42. H. Zimmer and R. D. Barry, J. Org. Chem., 1962, 27, 3710.
43. A. Yamaguchi and M. Okazaki, Nippon Kagaku Kaishi, 1973, 110
44. (Chem. Abstr., 1973, 78, 84494).
45. E. Napolitano, G. Spinelli, R. Fiaschi and A. Marsili, Synthesis, 1985, 38.
46. C. E. Castro, E. J. Gaughan and D. C. Owsley, J. Org. Chem., 1966, 31, 4071.
47. P. A. Chopard, R. F. Hudson and R. J. G. Searle, Tetrahedron Lett., 1965, 2357.
48. R. K. Howe, J. Org. Chem., 1973, 38, 4164.
49. C. F. Ingham, R. A. Massy-Westropp, G. D. Reynolds and W. D. Thorpe, Aust. J. Chem., 1975, 28, 2499.
50. R. S. Mali, S. R. Patil, B. K. Kulkarni and S. N. Yeola, Indian J. Chem., Sect. B, 1990, 29, 319;
51. R. S. Mali and S. R. Patil, Synth. Commun., 1990, 20, 167;
52. R. S. Mali and P. G. Jagtap, J. Chem. Res. (S), 1993, 184.
53. P. Hrnciar, A. Gaplovsky, V. Drgoncova and J. Donovalova, J. Chem. Pap., 1986, 40, 649
54. (Chem. Abstr., 1987, 106, 129037d).
55. A. Guirado, F. Barba, M. B. Hursthouse, A. Martinez and A. Areas, Tetrahedron Lett., 1986, 27, 4063.
56. R. F. Heck, Org. React., 1982, 27, 345; in
57. Palladium Reagents in Organic Synthesis, Academic Press, London, 1985;
58. A. J. de Meijere and F. F. Meyer, Angew. Chem., Int. Ed. Engl., 1994, 33, 2379;
59. W. Cabri and J. Candiani, Acc. Chem. Res., 1995, 28, 2.
60. Some selected references: T. K. Dougherty and K. S. Y. Lau, J. Org. Chem., 1983, 48, 5273;
61. Y. Zhang and E.-i. Negishi, J. Am. Chem. Soc., 1989, 111, 3454;
62. B. M. Trost, Acc. Chem. Res., 1990, 23, 34;
63. L. E. Overman, M. M. Abelman, D. J. Kucera, V. D. Trans and D. J. Ricca, Pure Appl. Chem., 1992, 64, 1813;
64. R. Grigg, S. Sukirthalingam and V. Sridharan, Tetrahedron Lett., 1991, 32, 2545;
65. F. E. Meyer, J. Brandenburg, P. J. Parsons and A. De Meijere, J. Chem. Soc., Chem. Commun., 1992, 390;
66. B. M. Trost and Y. Shi, J. Am. Chem. Soc., 1993, 115, 12491;
67. S. Brown, S. Clarkson, R. Grigg and V. Sridharan, Tetrahedron Lett., 1993, 34, 157;
68. S. Ma and E.-i. Negishi, J. Am. Chem. Soc., 1995, 117, 6345 and references cited therein.
69. L. S. Hegedus, Angew. Chem., Int. Ed. Engl., 1988, 27, 1113;
70. R. C. Larock, N. Berrios-Pena and K. Narayanan, J. Org. Chem., 1990, 55, 3447;
71. P. G. Anderson and J. E. Backvall, J. Am. Chem. Soc., 1992, 114, 8696;
72. J. E. Backvall and P. G. Andersson, J. Am. Chem. Soc., 1992, 114, 6374;
73. B. M. Trost and M. C. McIntosh, J. Am. Chem. Soc., 1995, 117, 7255;
74. R. C. Larock and E. K. Yum, Tetrahedron, 1996, 52, 2743;
75. R. Grigg, V. Loganathan and V. Sridharan, Tetrahedron Lett., 1996, 37, 3399.
76. D. E. Korte, L. S. Hegedus and R. K. Wirth, J. Org. Chem., 1977, 42, 1329.
77. R. C. Larock, S. Varaprath, H. H. Lau and C. A. Fellows, J. Am. Chem. Soc., 1984, 106, 5274.
78. D. Villemin and D. Goussu, Heterocycles, 1989, 29, 1255.
79. H. Y. Liao and C-H. Cheng, J. Org. Chem., 1995, 60, 3711.
80. N. G. Kundu, M. Pal, J. S. Mahanty and S. K. Dasgupta, J. Chem. Soc., Chem. Commun., 1992. 41.
81. N. G. Kundu, J. S. Mahanty, P. Das and B. Das, Tetrahedron Lett., 1993, 34, 1625.
82. C. Chowdhury and N. G. Kundu, Chem. Commun., 1996, 1067.
83. A. W. McCulloch and A. G. McInnes, Can. J. Chem., 1974, 52, 3569.
84. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 4467.
85. R. Rossi, A. Carpita and G. Bigelli, Tetrahedron Lett., 1985, 26, 523.
86. N. G. Kundu, M. Pal and C. Chowdhury, J. Chem. Res. (S), 1993, 432.
87. C. K. Bradsher and T. G. Wallis, J. Org. Chem., 1978, 43, 3817.
88. M. Protiva, V. Hnevsova-Seidlova, I. Jirkovsky and Z. Votava, Czech. Pat., 102 062, 1961
89. (Chem. Abstr., 1962, 57, 16 521).
90. N. A. Bumagin, A. B. Ponomaryov and I. P. Beletskaya, Synthesis, 1984, 728.
91. E. R. H. Jones and J. T. McCombie, J. Chem. Soc., 1942, 733;
92. K. N. Campbell, B. K. Campbell and L. T. Eby, J. Am. Chem. Soc., 1938, 60, 2882.
93. A. I. Vogel, A Text Book of Practical Organic Chemistry, ELBS, Longman, London, 4th edn., 1978, p. 697.
94. N. G. Kundu and S. A. Schmitz, J. Heterocycl. Chem., 1982, 19, 463.
95. H. L. Yale, J. Am. Chem. Soc., 1947, 69, 1547.