Access to indoles via Diels-Alder reactions of 3-vinylpyrroles

Journal of Heterocyclic Chemistry

Volumn 46, Issue 6, 2009, Pages 1285-1295

  Noland, Wayland E ^a   Lanzatella, Nicholas P ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 4 TOLUENESULFONYL 1H BENZO[G]INDOLE 6,9 DIONE; 1 4 TOLUENESULFONYL 1H NAPHTHO[2,3 G]INDOLE 6,11 DIONE; 1 4 TOLUENESULFONYL 4,5,5A ALPHA,11A ALPHA TETRAHYDRO 1H NAPHTHO[2,3 G]INDOLE 6,11 DIONE; 1 4 TOLUENESULFONYL 4,5,5A ALPHA,9A ALPHA TETRAHYDRO 1H BENZO[G]INDOLE 6,9 DIONE; 1 4 TOLUENESULFONYL 7ALPHA (1 4 TOLUENESULFONYL 1H PYRROL 3 YL) 4,5,6,7BETA TETRAHYDRO 1H INDOLE; 1H NAPHTHO[2,3 G]INDOLE 6,11 DIONE; 7 (4 ISOPROPYLPHENYL) 1 4 TOLUENESULFONYL 1H,7H BENZO[G]INDOLE 6,8 DIONE; 7 (4 ISOPROPYLPHENYL) 1 4 TOLUENESULFONYL 4,5,5A ALPHA,8A ALPHA TETRAHYDROPYRROLO 1H,7H BENZO[G]INDOLE 6,8 DIONE; 7 (4 ISOPROPYLPHENYL) 1 4 TOLUENESULFONYL 5,5A ALPHA,8A ALPHA,8B ALPHA TETRAHYDROPYRROLO 1H,7H BENZO[G]INDOLE 6,8 DIONE; 7 (4 ISOPROPYLPHENYL) 1H,7H BENZO[G]INDOLE 6,8 DIONE; 7 (4 PHENOXYPHENYL) 1 4 TOLUENESULFONYL 1H,7H BENZO[G]INDOLE 6,8 DIONE; 7 (4 PHENOXYPHENYL) 1 4 TOLUENESULFONYL 4,5,5A ALPHA,8A ALPHA TETRAHYDROPYRROLO 1H,7H BENZO[G]INDOLE 6,8 DIONE; 7 (4 PHENOXYPHENYL) 1 4 TOLUENESULFONYL 5,5A ALPHA,8A ALPHA,8B ALPHA TETRAHYDROPYRROLO 1H,7H BENZO[G]INDOLE 6,8 DIONE; 7 (4 PHENOXYPHENYL) 1H,7H BENZO[G]INDOLE 6,8 DIONE; BENZOQUINONE DERIVATIVE; INDOLE DERIVATIVE; MAGNESIUM; MALEIMIDE DERIVATIVE; MANGANESE OXIDE; METHANOL; N 4 TOLUENESULFONYL 3 VINYLPYRROLE; PYRROLE DERIVATIVE; TOLUENE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; AROMATIZATION; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; CYCLOADDITION; DEHYDROGENATION; DIELS ALDER REACTION; DIMERIZATION; DRUG SYNTHESIS; HUMAN; HUMAN CELL; ISOMERIZATION; MOUSE; NONHUMAN; SAPONIFICATION;

EID: 72249111979     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.228     Document Type: Article

References (96)

1. Sundberg, R. J. In Indoles; Katritzky, A. R., Meth-Cohn, O., Rees, C. W., Eds.; Academic Press: San Diego, 1996.
2. Gul, W.; Hamann, M. Life Sci 2005, 78, 442.
3. (a) Shen, T. Y.; Winter, C. A. Adv Drug Res 1977, 12, 89.
4. (b) Frishman, W. H. N Engl J Med 1983, 308, 940.
5. (c) He, L.; Chang, H.-X.; Chou, T.-C.; Savaraj, N.; Cheng, C. C. Eur J Med Chem 2003, 38, 101.
6. (d) Kuo, C.-C.; Hsieh, H.-P.; Pan, W.-Y.; Chen, C.-P.; Liou, J.-P.; Lee, S.-J.; Chang, Y.-L.; Chen, L.-T.; Chen, C.-T.; Chang, J.-Y. Cancer Res 2004, 64, 4621.
7. Noland, W. E.; Lanzatella, N. P.; Sizova, E. P.; Venkatraman, L.; Afanasyev, O. V. J Heterocycl Chem 2009, 46, 503.
8. Noland, W. E.; Wahlstrom, M. J.; Konkel, M. J.; Brigham, M. E.; Trowbridge, A. G.; Konkel, L. M. C.; Gourneau, R. P.; Scholten, C. A.; Lee, N. H; Condoluci, J. J.; Gac, T. S.; Mostafaei Pour, M.; Radford, P. M. J Heterocycl Chem 1993, 30, 81.
9. Noland, W. E.; Lanzatella, N. P.; Venkatraman, L.; Anderson, N. F.; Gullickson, G. C. J Heterocycl Chem 2009, in press.
10. (a) Jones, R. A.; Saliente, T. A.; Arques, J. S. J Chem Soc Perkin Trans I 1984, 2541.
11. (b) Jones, R. A.; Arques, J. S. Tetrahedron 1981, 37, 1597.
12. (c) Tao, M.; Park, C. H.; Bihovsky, R.; Wells, G. J.; Husten, J.; Ator, M. A.; Hudkins, R. L. Bioorg Med Chem Lett 2006, 16, 938.
13. (d) Muchowski, J. M.; Scheller, M. E. Tetrahedron Lett 1987, 28, 3453.
14. (e) Lee, C. K.; Bae, S. K.,Chung, B. Y.; Hahn, C. S. J Org Chem 1983, 48, 2488.
15. (f) Ohno, M.; Shimizu, S.; Eguchi, S. Heterocycles 1991, 32, 1199.
16. (g) Ohno, M.; Shimizu, S.; Eguchi, S. Tetrahedron Lett 1990, 31, 4613.
17. (h) Kim, H. H.; Goo, Y. M.; Lee, Y. Y. Bull Korean Chem Soc 1999, 20, 929.
18. (i) Keil, J.-M.; Kampchen, T.; Seitz, G. Tetrahedron Lett 1990, 31, 4581.
19. Jones, R. A.; Marriott, M. T. P.; Rosenthal, W. P.; Arques, J. S. J Org Chem 1980, 45, 4515.
20. Xiao, D.; Ketcha, D. M. J Heterocycl Chem 1995, 32, 499.
21. (a) Booth, R. J.; Lee, H. H.; Kraker, A.; Ortwine, D. F.; Palmer, B. D.; Sheehan, D. J.; Toogood, P. L. US Pat. App. Pub. 20,050,250,836 (2005); Chem Abstr 2005, 143, 460136.
22. (b) Kanai, F.; Murakata, C.; Tsujita, T.; Yamashita, Y.; Mizukami, T., Akinaga, S. PCT Int. Appl. WO 2,003,051,883; A1 20,030,626; CAN 139:69,289; AN 2003: 491, 229, 2003; Chem Abstr 2003, 139, 69289.
23. (c) Nagai, T.; Myokan, I.; Takashi, F.; Nomura, Y.; Mizutani, M.; Hori, T. Jpn. Pat. JP 3, 178,880, 1993; Chem Abstr 1994, 120, 106973.
24. Murase, M.; Yoshida, S.; Hosaka, T.; Tobinaga, S. Chem Pharm Bull 1991, 39, 489.
25. Hodges, L. M.; Spera, M. L.; Moody, M. W.; Harman, W. D. J Am Chem Soc 1996, 118, 7117.
26. Jones G., II.; Gilow, H. M.; Low, J. J Org Chem 1979, 44, 2949.
27. Candy, C. F.; Jones, R. A.; Wright, P. H. J Chem Soc C 1970, 18, 2563.
28. Rokach, J.; Hamel, P.; Kakushima, M. Tetrahedron Lett 1981, 22, 4901.
29. (a) Xu, R. X.; Anderson, H. J.; Gogan, N. J.; Loader, C. E.; McDonald, R. Tetrahedron Lett 1981, 22, 4899.
30. (b) Kakushima, M.; Hamel, P.; Frenette, R.; Rokach, J. J Org Chem 1983, 48, 3214.
31. (c) Anderson, H. J.; Loader, C. E.; McDonald, R.; Edwards, L. G. Can J Chem 1985, 63, 896.
32. (d) Anderson, H. J.; Loader, C. E. Synthesis 1985, 353.
33. Settambolo, R.; Lazzaroni, R.; Messeri, T.; Mazzetti, M.; Salvadori, P. J Org Chem 1993, 58, 7899.
34. Huffman, J. W.; Smith, V. J.; Padgett, L. W. Tetrahedron 2008, 64, 2104.
35. (a) Waser, J.; Gaspar, B.; Nambu, H.; Carreira, E. M. J Am Chem Soc 2006, 128, 11693.
36. (b) Wrackmeyer, B.; Schwarze, B. J Organomet Chem 1997, 534, 181.
37. (c) Overberger, C. G.; Wartman, A.; Salamone, J. C. Org Prep Proced Int 1969, 1, 117.
38. (d) Jones, R. A.; Lindner, J. A. Aust J Chem 1965, 18, 875.
39. Foitzik, R. C.; Kaynak, A.; Pfeffer, F. M. Tetrahedron 2007, 63, 4237.
40. Cava, M. P.; Deana, A. A.; Muth, K.; Mitchell, M. J. Org Synth Coll 1973, 5, 944.
41. Rummens, F. H. A.; Kaslander, L. Can J Spectrosc 1972, 17, 99.
42. (a) Miyagi, Y.; Maruyama, K.; Tanaka, N.; Sato, M.; Tomizu, T.; Isogawa, Y.; Kashiwano, H. Bull Chem Soc Jpn 1984, 57, 791.
43. (b) Kienzle, F.; Mergelsberg, I.; Stadlwieser, J.; Arnold, W. Helv Chim Acta 1985, 68, 1133.
44. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett 1979, 20, 3437.
45. (a) Hilt, G.; Luers, S.; Smolko, K. I. Org Lett 2005, 7, 251.
46. (b) Lorvelev, G.; Vaultier, M. Tetrahedron Lett 1998, 39, 5185.
47. (c) Rasset, C.; Vaultier, M. Tetrahedron 1994, 50, 3397.
48. (d) Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743.
49. (e) Martinez-Fresneda, P.; Vaultier, M. Tetrahedron Lett 1989, 30, 2929.
50. (f) Matteson, D. S.; Hagelee, L. A. 1975, 93, 21.
51. (g) Woods, W. G.; Bengelsdorf, I. S. J Org Chem 1966, 31, 2769.
52. (h) Mikhailov, B. M; Bubnov, Y. N. Izv Akad Nauk Ser Khim 1964, 2170.
53. (i) Matteson, D. S.; Waldbillig, J. O. J Org Chem 1963, 28, 366.
54. (a) Singleton, D. A.; Martinez, J. P. J Am Chem Soc 1990, 112, 7423.
55. (b) Singleton, D. A.; Martinez, J. P.; Watson, J. V.; Ndip, G. M. Tetrahedron 1992, 48, 5831.
56. (a) Matteson, D. S.; Waldbillig, J. O. J Org Chem 1963, 28, 366.
57. (b) Evans, D. A.; Scott, W. L.; Truesdale, L. K. Tetrahedron Lett 1972, 13, 121.
58. Woods, W. G.; Bengelsdorf, I. S. J Org Chem 1966, 31, 2769.
59. Titov, J. A. Russ Chem Rev 1962, 31, 267.
60. Sauer, J.; Sustmann, R. Angew Chem Int Ed Engl 1980, 19, 779.
61. Li, C.; Johnson, R. P.; Porco J. A., Jr. J Am Chem Soc 2003, 125, 5095.
62. Nasielski, J.; Siberdt, F.; De Bue, G. Bull Soc Chim Belg 1994, 103, 719.
63. (a) Narasimhan, N. S.; Kusurkar, R. S.; Dhavale, D. D. Indian J Chem 1983, 22B, 1004.
64. (b) Pindur, U.; Kim, M.-H. Tetrahedron 1989, 45, 6427.
65. (c) Blechert, S.; Knier, R.; Schroers, H.; Wirth, T. Synthesis 1995, 592.
66. (d) Blechert, S.; Wirth, T. Tetrahedron Lett 1992, 33, 6621.
67. Ziegler, F. E.; Spitzner, E. B.; Wilkins, C. K. J Org Chem 1971, 36, 1759.
68. (a) Iwagawa, T.; Miyazaki, M.; Yokogawa, Y.; Okamura, H.; Nakatani, M.; Doe, M.; Morimoto, Y.; Takemura, K. Heterocycles 2008, 75, 2023.
69. (b) Acheson, R. M.; Bridson, J. N.; Cecil, T. R.; Hand, A. R. J Chem Soc Perkin Trans 1 1972, 26, 1569.
70. (c) Campbell, R. W. Ph.D. Thesis; University of Minnesota: Minnesota 1961, 44. Available from: Dissertations & Theses @ CIC Institutions. Accessed March 10, 2009, Publication Number: AAT 6201767.
71. Bergman, J.; Carlsson, R. Tetrahedron Lett 1978, 19, 4055.
72. Soares, M. I. L.; Lopes, S. M. M.; Cruz, P. F.; Brito, R. M. M.; Pinho e Melo, T. M. V. D. Tetrahedron 2008, 64, 9745.
73. Houk, K. N. J Am Chem Soc 1973, 95, 4092.
74. (a) Korchowiec, J. J Mol Struct (Theochem) 2003, 663, 175.
75. (b) Mariet, N.; Pellissier, H.; Parrain, J.-L.; Santelli, M. Tetrahedron 2004, 60, 2829.
76. Fleming, I.; Gianni, F. L.; Mah, T. Tetrahedron Lett 1976, 17, 881.
77. (a) Seebach, D. Angew Chem Int Ed Engl 1979, 18, 239.
78. (b) Seebach, D.; Corey, E. J. J Org Chem 1975, 40, 231.
79. (a) Fatiadi, A. J. Synthesis 1976, 65.
80. (b) Giovanoli, R.; Stahli, E.; Feitknecht, W.,Helv Chim Acta 1970, 53, 453.
81. (c) Giovanoli, R.; Bernhard, K.; Feitknecht, W. Helv Chim Acta 1968, 51, 355.
82. (d) Vereshchagin, L. I.; Gainulina, S. R.; Podskrebysheva, S. A.; Gaivoronskii, L. A.; Okhapkina, L. L.; Vorob-eva, V. G.; Latyshev, V. P. J Org Chem USSR (Engl Transl) 1972, 8, 1143.
83. (a) Lee, G. H., Youn, I. K.; Choi, E. B.; Lee, H. K.; Yon, G. H.; Rang, H. C.; Pak, C. S. Curr Org Chem 2004, 8, 1263.
84. (b) Nyasse, B.; Grehn, L.; Ragnarsson, U. Chem Commun 1997, 1017.
85. (c) Yokoyama, Y.; Matsumoto, T.; Murakami, Y. J Org Chem 1995, 60, 1486.
86. Shvartsberg, M. S.; Moroz, A. A.; Piskunov, A. V.; Budzinskaya, I. A. Bull Acad Sci USSR Div Chem Sci 1987, 36, 2338.
87. Yasuhara, A.; Sakamoto, T. Tetrahedron Lett 1998, 39, 595.
88. Magnus, P.; Sear, N. L.; Kim, C. S.; Vicker, N. J Org Chem 1992, 57, 70.
89. Haskins, C. M.; Knight, D. W. Tetrahedron Lett 2004, 45, 599.
90. (a) Afonso, A.; Kelly, J.; Puar, M. S.; McCombie, S.; McPhail, A. T. Tetrahedron Lett 1998, 39, 7661.
91. (b) Cox, J. P. L.; Craig, A. S.; Helps, I. M.; Jankowski, D. P.; Eaton, M. A. W.; Millican, A. T.; Millar, K.; Beeley, N. R. A.; Boyce, B. A. J Chem Soc Perkin Trans I 1990, 44, 2567.
92. Jackson, Y. A.; Billimoria, A. D.; Sadanandan, E. V.; Cava, M. P. J Org Chem 1995, 60, 3543.
93. (a) Pringel, E.; Gentili, J.; Terreux, R.; Fenet, B.; Barret, R. Lett Org Chem 2005, 2, 378.
94. (b) Mahboobi, S.; Sellmar, A.; Eichhorn, E.; Beckers, T.; Fiebig, H.-H.; Kelter, G. Eur J Med Chem 2005, 40, 85.
95. Yamago, S.; Miyazoe, H.; Lida, K.; Yoshida, J.-I. Org Lett 2000, 2, 3671.
96. Carreno, C. M.; Garcia-Cerrada, S.; Urbano, A. Chem Eur J 2003, 9, 4118.