The Synthesis of isocoumarins over the last decade. A review

Organic Preparations and Procedures International

Volumn 29, Issue 6, 1997, Pages 631-664

  Napolitano, Elio ^a  

^a SCUOLA NORMALE SUPERIORE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ISOCOUMARINS;

EID: 0347419646     PISSN: 00304948     EISSN: 19455453     Source Type: Journal    
DOI: 10.1080/00304949709355245     Document Type: Review

References (138)

1. R. D. Barry, Chem. Rev., 64, 229 (1964).
2. N. S. Narasimhan and R. S. Mali, Topics in Current Chemistry, 138, 63 (1987);
3. N. S. Narasimhan and R. S. Mali, Synthesis, 63 (1983).
4. R. A. Hill, “Naturally Occurring Isocoumarins” in Progress in the Chemistry of Natural Compounds, Vol. 49, p. 1, W. Herz, H. Griesebach, G. W. Kirby and C. Tamm Eds., Springer Verlag, Wien (1986).
5. B. V. Me Inemey and W. C. Taylor, “The Xenocoumarins and Related Biologically Active Dihydroisocoumarins” in Studies in Natural Compound Chemistry, Vol. 15, p. 381, Atta-ur-Rahman Ed., Elsevier, Amsterdam (1995).
6. T. J. Simpson “Aromatic Compounds” in The Natural Compounds Chemistry, A. P. Thompson Ed., Blakie, Glasgow (1985).
7. J. D. Hepworth, “Pyrans and Fused Pyrans: (iii) Synthesis and Applications” in Comprehensive Heterocyclic Chemistry, Vol. 3, p. 737, Pergamon, Oxford (1984);
8. J. D. Hepworth, C. D. Gabbutt and B. M. Heron, “Pyrans and their Benzo Derivatives: Synthesis”, in Comprehensive Heterocyclic Chemistry II, Vol. 5, p. 436, Pergamon, Oxford (1996).
9. F. M. Hauser and V. M. Boghdanov, J. Org. Chem., 53, 4676 (1988).
10. M. Watanabe, M. Sahara, M. Kubo, S. Furukawa, R. J. Billedeau and V. Snieckus, J. Org. Chem., 49, 742 (1984).
11. V. Snieckus, Chem. Rev., 90, 879 (1990).
12. S. Superchi, F. Minutolo, D. Pini and P. Salvadori, J. Org. Chem., 61, 3183 (1996).
13. T. K. Park and S. J. Danishefsky, Tetrahedron Lett., 36, 195 (1995).
14. G. L. Grünewald and V. H. Dahanukar, J. Heterocyclic Chem., 31, 1609 (1994).
15. T. G. Gant and A. I. Meyers, Tetrahedron, 50, 2297 (1994).
16. H. J. Bestmann, F. Kern, D. Schäfer and M. C. Witschel, Angew. Chem. Int. Ed. Engl, 31, 795 (1992).
17. N. Choukchou-Braham, Y. Asakawa and J. P. Lepoittevin, Tetrahedron Lett., 35, 3949 (1994).
18. B. H. Bhide, V. D. Akolkar and D. I. Brahmbhat, Indian. J. Chem. Sect. B, 31(B), 116 (1992).
19. H. Paulsen and M. Stubbe, Ann., 535 (1983).
20. G. E. Keck, S. F. McHardy and J. A. Murry, J. Am Chem. Soc., 117, 7289 (1995).
21. D. R. Gauthier Jr. and S. L. Bender, Tetrahedron Lett., 37, 13 (1996).
22. K. Mallareddy and S. P. Rao, Tetrahedron, 52, 8535 (1996)
23. N. J. Srivastava, P. K. Kumar, S. N. Thakur, L. K. Sahay and S. Srivastava, Indian J. Chem. Soc., 67, 210 (1990).
24. R. Beugelmans, J. Chastanet, H. Ginsburg, L. Quintero-Cortes and G. Roussi, J. Org. Chem, 50, 4933 (1985).
25. H. L. Aalten, G. van Koten, K. Vrieze and A. van der Kerk-van Hoof, Rec. Trav Chim. Paysbas, 109, 46 (1990) and references cited therein.
26. M. Durandetti, J.-Y. Nedelec and J. Perichon, J. Org. Chem, 61, 1748 (1996).
27. S. H. Reich, M. Melnick, M. J. Pino, M. A. M. Fuhry, A. J. Trippe, K. Appelt, J. F. Davies II, B. W. Wu and L. Musick, J. Med. Chem., 39, 2781 (1996).
28. A. Takle and P. Kocienski, Tetrahedron, 46, 4503 (1990).
29. T. Sakamoto, Y. Kondo, A. Yasuhara and H. Yamanaka, Tetrahedron., 47, 1877 (1991).
30. D. E. Korte, L. S. Hegedus and R. K. Wirth, J. Org. Chem, 42, 1329 (1977).
31. T. Minami, A. Nishimoto and M. Hanaoka, Tetrahedron Lett., 36, 9505 (1995);
32. T. Minami, A. Nishimoto, Y. Nakamura and M. Hanaoka, Chem. Pharm. Bull. Jpn, 42, 1700 (1994).
33. T. Izumi, Y. Nishimoto, K. Kohei and A. Kasahara, J. Heterocyclic Chem., 27, 1419 (1990);
34. T. Izumi and N. Morishita, J. Heterocyclic Chem., 31, 145 (1994).
35. M. M. Abelman, L. E. Overman and V. D. Tran, J. Am. Chem. Soc., 112, 6959 (1990).
36. R. C. Larock, E. K. Yum, M. J. Doty and K. K. C. Sham, J. Org. Chem., 60, 3270 (1995).
37. K. Okuro, M. Furuune, M. Enna, M. Miura and M. Nomura, J. Org. Chem., 58, 4716 (1993) and references cited therein.
38. H.-Y. Liao and C.-H. Cheng, J. Org. Chem., 60, 3711 (1995)
39. Y. Ogawa, M. Maruno and T. Wakamatsu, Heterocycles, 41, 2587 (1995);
40. N. G. Kundu and M. Pal, Chem. Commun., 86 (1993).
41. A. Nagarajan and T. R. Balasubramanian, Indian. J. Chem. Sect. B, 27B, 380 (1988).
42. N. Menashe and Y. Shvo, J. Org. Chem, 58, 7434 (1993).
43. B. H. Bhide, V. D. Akolkar and V. G. Prabhu, Indian J. Chem, Sect. B, 31B, 143 (1992).
44. L. M. Harwood J Chem. Soc. Perkin Trans. I, 2511 (1984);
45. E. Occelli, A. DePaoli and G. Nathansohn, Gazz. Chim. Ital., 111, 383 (1981).
46. A. Saeed and N. H. Rama, J. Chem. Soc. Pat, 15, 212 (1993); Chem. Abstr., 120, 322-9840 (1993).
47. M. Yamato, K. Hashigaki, M. Ikeda, H. Ohtake and K. Tasaka, J. Med. Chem., 24, 194 (1981).
48. B. H. Bhide, V. D. Akolkar and D. I. Brahmbhat, Proc. Indian. Acad. Sei. (Chem. Sei.), 101, 301; Chem. Abstr., 112, 198053s (1989).
49. A. G. Schultz and S. J. Kirincich, J. Org. Chem., 61, 5631 (1996).
50. M. T. Reetz and K. Töllner, Tetrahedron Lett., 36, 9461 (1995).
51. J. Katakawa, H. Meguri and H. Irie, Heterocycles, 22, 2213 (1984).
52. N. S. Narasimhan and C. P. Bapat, J. Chem Soc. Perkin Trans. 1, 2099 (1982).
53. N. H. Rama, A. Saeed and C. W. Bird, Ann., 711 (1995);
54. N. H. Rama, A. Saeed and C. W. Bird, Ann. 1331 (1993);
55. N. H. Rama, R. Iqbal, A. Saeed and S. Hameed, J. Chem. Soc. Pat, 14, 138 (1992); Chem. Abstr., 118, 168861 (1993);
56. N. H. Rama, R. Iqbal, A. Saeed and S. Hameed, J. Chem. Soc. Pat, 13, 45 (1991); Chem. Abstr., 115, 207712 (1991).
57. J. Sinha, R. P. Singh and J. N. Srivastava, J. Indian Chem. Soc., 63, 907 (1986);
58. H. N. Singh and R. P. Singh, J. Indian Chem. Soc., 65, 685 (1988).
59. E. Napolitano, E. Giannone, R. Fiaschi and A. Marsili, J. Org. Chem., 48, 3653 (1983);
60. E. Napolitano, A. Ramacciotti and R. Fiaschi, Gazz. Chim. Ital., 118, 101 (1988);
61. E. Napolitano, M. Morsani and R. Fiaschi, Gazz. Chim. Ital., 121, 249 (1991);
62. E. Napolitano, A. Ramacciotti, M. Morsani and R. Fiaschi, Gazz. Chim. Ital., 121, 257 (1991);
63. E. Napolitano, Gazz. Chim. Ital., 121, 455 (1991);
64. E. Napolitano, L. Bertelli and R. Fiaschi, Gazz. Chim. Ital., 123, 669 (1993);
65. E. Napolitano, A. Ramacciotti and R. Fiaschi, J. Org. Chem., 61, 5371 (1996);
66. A. Ramacciotti, R. Fiaschi and E. Napolitano, Gazz. Chim. Ital, 125, 111 (1995).
67. H. Kotsuki, A. Miyazaki and M. Ochi, Chemistry Lett., 1255 (1992).
68. F. Wendelin and R. R. Schmidt, Carbohydr. Res., 209, 101 (1991).
69. R. C. Larock and C. A. Fellows, J. Am. Chem. Soc., 104, 1900 (1982).
70. M. Mori, K. Chiba, N. Inotsume and Y. Ban, Heterocycles, 12, 921 (1979).
71. J. H. Tidwell, A. J. Peat and S. L. Buchwald, J. Org. Chem., 59, 7164 (1994).
72. E. Negishi, C. Coperet, T. Sugihara, I. Shimoyama, Y. Zhang, G. Wu and J. M. Tour, Tetrahedron, 50, 425 (1994).
73. R. D. Clark and A. Jahangir, Org. React., 47, 1 (1995).
74. V. H. Deshpande, B. Rai and R. A. Khan, Tetrahedron, 52, 7159 (1996).
75. C. McNicholas, T. J. Simpson and N. J. Willet, Tetrahedron Lett., 37, 8053 (1996);
76. M. P. Dillon, T. J. Simpson and J. B. Sweeney, Tetrahedron Lett., 33, 7569 (1992).
77. R. A. Ward and G. Procter, Tetrahedron, 51, 12301 (1995). For other syntheses see ref. 11 and references cited therein.
78. J. H. P. Tyman and N. Visani, J. Chem. Research, 14 (1997);
79. T. R. Kelly, C. T. Jagoe and Q. Li, J. Am. Chem. Soc., III, 4522 (1989).
80. R. C. Thompson and J. Kallmerten, J. Org. Chem, 55, 60-76 (1990).
81. J. A. Wendt, P. J. Gauvreau and R. D. Bach, J. Am. Chem. Soc., 116, 9921 (1994).
82. A. V. R. Rao, J. S. Jadav, K. K. Reddy and V. Upender, Tetrahedron Lett., 38, 5199 (1991).
83. S. Ohta, Y. Kamata, T. Inagaki, Y. Masuda, S. Yamamoto, M. Yamashita and I. Kawasaki, Chem. Pharm. Bull. Jpn, 41, 1188 (1993).
84. K. C. Hildebran, T. L. Cordray, K. W. Chan and C. F. Beam, Synth. Commun., 24, 779 (1994).
85. L. Crenshaw, S. P. Khanapure, U. Siriwardane and E. R. Biehl, Tetrahedron Lett., 29, 3777 (1988).
86. W. Han, Y. Lu, H. Zhao, M. Dutt, E. R. Biehl, Synthesis, 59 (1996).
87. R. J. Mills, N. J. Taylor and V. Snieckus, J. Org. Chem. 54, 43-72 (1989).
88. S. V. Kessar, P. Singh, R. Vohra, N. P. Kaur and D. Venugopar, J. Org. Chem., 57, 6716 (1992).
89. R. Connors, E. Tran and T. Durst, Can. J. Chem., 74, 221 (1996).
90. E. Napolitano, G. Spinelli, R. Fiaschi and A. Marsili, J. Chem. Soc. Perkin Trans. I, 2565 (1987).
91. T. Kanda, S. Kato, T. Sugino, N. Kambe, A. Ogawa and N. Sonoda, Synthesis, 1103 (1995).
92. L. Colombo, C. Gennari, M. Santandrea, E. Narisano and C. Scolastico, J. Chem. Soc. Perkin Trans. I, 136 (1980).
93. G. A. Kraus and J. Ridgeway, J. Org. Chem., 59, 4735 (1994).
94. J. J. Fitzgerald, A. R. Pagano, V. M. Sakoda and R. A. Olofson, J. Org. Chem., 59, 4117 (1994).
95. K. Shishido, K. Hiroya, A. Yamashita, Y. Tokunaga and K. Fukumoto, Heterocycles, 30, 253 (1990).
96. U. Azzena, S. Demartis and G. Melloni, J. Org. Chem., 61, 4913 (1996).
97. H. Kaji, M. Yamada, K. Nozawa, K. Kawai and S. Nakajima, Org. Prep. Proc. Int., 18, 253 (1986).
98. M. Guyot and D. Molho, Tetrahedron. Lett., 14, 3433 (1973).
99. M. D. Shair, T. Y. Yoon, K. K. Mosny, T. C. Chou and S. J. Danishefsky, J. Am. Chem. Soc., 118, 9509 (1996).
100. A. Saeed, N. H. Rama, J. Chem. Soc. Pak., 16, 220 (1994); Chem. Abstr., 123, 9192 (1995).
101. G. Mehta, S. R. Shah and Y. Venkateswarlu, Tetrahedron, 50, 11729 (1994).
102. K. A. Parker and G. A. Breault, Tetrahedron Lett., 27, 3835 (1986).
103. C. N. Lewis, J. Staunton and D. C. Sunter, J. Chem. Soc. Perkin Trans. I, 747 (1988).
104. R. S. Mali and D. W. Shelke, Indian J. Chem. Sect. B, 32B, 822 (1993);
105. R. S. Mali, P. G. Jagtap, S. R. Patil and P. N. Pawar, Chem. Commun., 883 (1992).
106. H. Natsugari, Y. Ikeura, Y. Kiyota, Y. Ishichi, T. Ishimaru, O. Saga, H. Shirafuji, T. Tanaka, T. Kamo, T. Doi and M. Otsuka, J. Med. Chem., 38, 3106 (1995).
107. E. Napolitano and A. Ramacciotti, Gazz. Chim. Ital, 117, 443 (1987).
108. S. U. Kulkami and L. R. N. Usgaonkar, J. Indian. Chem. Soc., 68, 525 (1991).
109. A. Ghose and J. N. Srivastava, Indian J. Heterocycl. Chem., 1, 241 (1992).
110. M. Yamaguchi, T. Okuma, A. Horiguchi, C. Ikeura and T. Minami, J. Org. Chem., 57, 1647 (1992);
111. M. Yamaguchi, T. Okuma, S. Nakamura and T. Minami, J. Chem. Soc. Perkin Trans. I, 183 (1990).
112. M. Yamaguchi, K. Hasebe, H. Higashi, M. Uchida, A. Irie and T. Minami, J. Org. Chem., 55, 1611 (1990).
113. K. Krohn, E. Roemer and M. Top, An., 271 (1996).
114. V. G. Gore and N. S. Narasimhan, Indian J. Chem. Sect. B, 30B, 241 (1991).
115. R. C. Larock and H. Yong, Synlett, 748 (1994).
116. R. H. Carter, M. J. Garson, R. A. Hill, J. Stounton and D. C. Sunter, J. Chem. Soc. Perkin Trans. 1, 471 (1981);
117. R. H. Carter, R. M. Coyler, R. A. Hill and J. Stounton, J. Chem. Soc. Perkin Trans, 1438 (1976).
118. A. Ichihara, M. Hashimoto, T. Hirai, I. Takeda, Y. Sasamura, S. Sakamura, R. Sato and A. Tajimi, Chemistry Lett., 1495 (1989).
119. J. K. Kendall, T. H. Fisher, H. P. Schultz and T. P. Schultz, J. Org. Chem., 54, 4218 (1989)
120. T. Funata, Y. Fukuyama and Y. Asakawa, Phytochemistry, 25, 517 (1986).
121. M. E. Botha, R. G. F. Giles, C. M. Moorhoff, L. M. Engelhardt, A. H. White, A. lardine and S. C. Yorke, J. Chem. Soc. Perkin Trans. I, 89 (1991).
122. J. Delaunay and J. Simonet, Tetrahedron Lett., 29, 543 (1988).
123. F. Johnson and E. R. Marinelli, J. Org. Chem., 51, 3911 (1986).
124. R. M. Letcher, K-W. Ng and K. K. Cheung, Chem. Commun., 1602 (1987).
125. G. Sartori, F. Bigi, X. Tao, G. Casnati and G. Canali, Tetrahedron Lett., 33, 4771 (1992).
126. K. Katsuta, N. Kojima, M. Chino, S. Kawazoe and M. Nakata, Tetrahedron Lett., 34, 4961 (1993).
127. A. V. Rama Rao, A. K. Singh, B. V. Rao and K. M. Reddy, Heterocycles, 37, 1893 (1994).
128. N. Takeuchi, T. Nakano, K. Goto and S. Tobinaga, Heterocycles, 35, 289 (1993).
129. N. Takeuchi, K. Goto, Y. Sasaki, T. Fujita, K. Okazaki, K. Kamata and S. Tobinaga, Heterocycles, 33, 357(1992).
130. C. A. Broka, Tetrahedron Lett., 32, 859 (1991).
131. T. A. Carpenter, G. E. Evans, F. J. Leeper, J. Staunton and M. R. Wilkinson, J. Chem. Soc. Perkin Trans. 1, 1043 (1984).
132. C. C. Kanakam, N. S. Mani, H. Ramanathan and G. S. R. Subba Rao, J. Chem. Soc. Perkin Trans., 1907 (1989).
133. A. Amoldi, A. Bassoli, L. Merlini and E. Ragg, Gazz. Chim. Ital., 122, 403 (1992).
134. A. S. Cotterill, M. Gill and N. M. Milanovic, J. Chem. Soc. Perkin Trans. I, 1217 (1995).
135. S. J. Neeson and P. J. Stevenson, Tetrahedron, 45, 6239 (1989).
136. O. Duval and L. Mavoungou Gomès, Tetrahedron, 46, 1253 (1990).
137. H.-J. Wu, S.-H. Linn and C.-C. Lin, Heterocycles, 38, 1507 (1994).
138. M. C. Roux, L. Wartski, M. Nierlich, D. Vigner and M. Lance, Tetrahedron, 50, 8445 (1994).