Synthesis of nitrogen heterocycles using the intramolecular Pummerer reaction

Current Organic Chemistry

Volumn 4, Issue 2, 2000, Pages 175-203

  Padwa, Albert ^a   Waterson, Alex G ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; NITROGEN DERIVATIVE; SULFOXIDE;

CYCLIZATION; MOLECULAR INTERACTION; ORGANIC CHEMISTRY; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034038966     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/1385272003376300     Document Type: Review

References (99)

1. Pummerer, R. Chem. Ber. 1909, 42, 2282.
2. Russell, G. A.; Mikol, G. J. In Mechanisms of Molecular Migration; Thyagaragan, B. S., Ed.; Wiley Interscience: New York, 1968; Vol. 1, pp 157-207.
3. DeLucchi, O.; Miotti, U.; Modena, G. Organic Reactions; Raquette, L. A., Ed.; John Wiley: 1991; Chap. 3, pp 157-184.
4. Grierson, D. S.; Husson, H. P. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, 1991; Vol. 6, pp 909-947.
5. Oae, S.; Numata, T. The Pummerer Type of Reactions in Isotopes in Organic Chemistry, Buncel, E.; Lee, C. E., Eds.; Elsevier: New York, 1980; Vol. 5, Chapter 2.
6. Kennedy, M; McKervey, M. In Comprehensive Organic Chemistry; Trost, B.M.; Fleming, I., Eds; Pergamon Press: Oxford, 1991; Vol. 7, p. 193.
7. Bates, D. K. J. Org. Chem. 1977, 42, 3452.
8. Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1976, 41, 1118.
9. Padwa, A.; Gunn, D. E., Jr.; Osterhout, M. H. Synthesis 1997, 1353.
10. Strunz, G. M.; Findlay, J. A. The Alkaloids; Academic Press: New York, 1985; Vol. 26, p. 89.
11. Comprehensive Heterocyclic Chemistry, Katritzky, A.; Rees, C. W.; Scriven, E. F. V., Elsevier Science Ltd: Oxford, U. K., 1996.
12. Takano, S.; Iida, H.; Inomata, K.; Ogasawara, K. Heterocycles 1993, 35, 47.
13. Tamura, Y.; Maeda, H.; Akai, S.; Ishiyama, K.; Ishibashi, H. Tetrahedron Lett. 1981, 22, 4301.
14. Ishibashi, H.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1987, 1099.
15. Ishibashi, H.; Ozeki, H.; Ikeda, M. J. Chem. Soc., Chem. Commun. 1986, 654.
16. Shinohara, T.; Toda, J.; Sano, T. Chem. Pharm. Bull. 1997, 45, 813.
17. Tamura, Y.; Uenishi, J. I.; Maeda, H.; Choi, H. D.; Ishibashi, H. Synthesis 1981, 534.
18. Tamura, Y.; Uenishi, J. I.; Choi, H. D.; Haruta, J. I.; Ishibashi, H. Chem. Pharm. Bull. 1984, 32, 1995
19. Lee, A. W. M.; Chan, W., H.; Mo, T. Tetrahedron Lett. 1997, 38, 3001.
20. Okamura, K.; Yamada, S. Chem. Pham. Bull. 1978, 26, 2305.
21. Ishibashi, H.; Harada, S.; Okada, M.; Somekawa, M.; Kido, M.; Ikeda, M. Chem. Pharm. Bull. 1989, 37,939.
22. Ishibashi, H.; Okada, M.; Akiyama, A.; Nomura, K.; Ikeda, M. J. Heterocyclic Chem. 1986, 23, 1163.
23. Ishibashi, H.; Kawanami, H.; Iriyama, H.; Ikeda, M. Tetrahedron Lett. 1995, 36, 6733.
24. Ishibashi, H.; Takagaki, K.; Imada, N.; Ikeda, M. Tetrahedron 1994, 50, 10215. Ishibashi, H.; Takagaki, K.; Imada, N.; Ikeda, M. Synlett 1994, 49.
25. Ishibashi, H.; Takagaki, K.; Imada, N.; Ikeda, M. Tetrahedron 1994, 50, 10215. Ishibashi, H.; Takagaki, K.; Imada, N.; Ikeda, M. Synlett 1994, 49.
26. Tamura, Y.; Maeda, H.; Akai, S.; Ishibashi, H. Tetrahedron Lett. 1982, 23, 2209.
27. Ishibash H.; Sato, K.; Maruyama, K.; Ikeda, M.; Tamura, Y. Chem. Pharm. Bull. 1985, 33, 4593.
28. Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1976, 41, 1118. Oikawa, Y.; Yonemitsu, O. J. Chem. Soc., Perkin Trans. 1 1976, 1479. Oikawa, Y.; Yonemitsu, O. Heterocycles 1976, 5, 233.
29. Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1976, 41, 1118. Oikawa, Y.; Yonemitsu, O. J. Chem. Soc., Perkin Trans. 1 1976, 1479. Oikawa, Y.; Yonemitsu, O. Heterocycles 1976, 5, 233.
30. Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1976, 41, 1118. Oikawa, Y.; Yonemitsu, O. J. Chem. Soc., Perkin Trans. 1 1976, 1479. Oikawa, Y.; Yonemitsu, O. Heterocycles 1976, 5, 233.
31. Bates, D. K.; Tafel, K. A. J. Org. Chem. 1994, 59, 8076.
32. Picard, J. A.; Chen, S.; Bates, D. K. Heterocycles 1994, 38, 1775.
33. Bates, D. K.; Habib, Q. A. J. Heterocyclic Chem. 1995, 32, 1477.
34. Tafel, K. A.; Bates, D. K. J. Org. Chem. 1992, 57, 3676.
35. Wang, H. M.; Lin, M. C.; Chen, L. C. J. Chinese Chem. Soc. 1994, 41, 217.
36. Wang, H. M.; Lin, M. C.; Chen, L. C. Heterocycles 1994, 38, 1519.
37. Gallagher, T.; Magnus, P. J. Am. Chem. Soc. 1982, 104, 1140.
38. Gallagher, T.; Magnus, P.; Huffman, J. C. J. Am. Chem. Soc. 1983, 105, 4750.
39. Magnus, P.; Giles, M.; Bonnert, R.; Johnson, G.; McQuire, L.; Deluoa, M.; Merritt, A.; Kim, C. S.; Vicker, N. J. Am. Chem. Soc. 1993, 115, 8116.
40. Ladlow, M.; Cairns, P. M.; Magnus, P. J. Chem. Soc., Chem. Commun. 1986, 1756.
41. Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35.
42. Bonjoch, J.; Catena, J.; Valls, N. J. Org. Chem. 1996, 61, 7106.
43. Desmar̈le, D.; d'Angelo, J. J. Org. Chem. 1994, 59, 2292.
44. Catena, J.; Valls, N.; Bosch, J.; Bonjoch, J. Tetrahedron Lett. 1994, 35, 4433.
45. Cardwell, K.; Hewitt, B.; Magnus, P. Tetrahedron Lett. 1987, 28, 3303.
46. Gallagher, T.; Magnus, P. J. Am. Chem. Soc. 1983, 105, 2086.
47. Magnus, P.; Gallagher, T.; Brown, P.; Huffman, J. C. J. Am. Chem. Soc. 1984, 106, 2105.
48. Bennasar, M. -L.; Vidal, B.; Sufi, B. A.; Bosch, J. Chem. Commun. 1998, 2639.
49. Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299. Amat, M.; Bosch, J. J. Org. Chem. 1992, 57, 5792.
50. Amat, M.; Linares, A.; Bosch, J. J. Org. Chem. 1990, 55, 6299. Amat, M.; Bosch, J. J. Org. Chem. 1992, 57, 5792.
51. Amat, M.; Bennasar, M. L.; Hadida, S.; Sufi, B. A.; Zulaica, E.; Bosch, J. Tetrahedron Lett. 1996, 37, 5217.
52. Bennasar, M. L.; Zulaica, E.; Ramlrez, A.; Bosch, J. Tetrahedron Lett. 1996, 37, 6611. Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158.
53. Bennasar, M. L.; Zulaica, E.; Ramlrez, A.; Bosch, J. Tetrahedron Lett. 1996, 37, 6611. Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158.
54. Kawasaki, T.; Suzuki, H.; Sakata, I.; Nakanishi, H.; Sakamoto, M. Tetrahedron Lett. 1997, 38, 3521.
55. Bates, D.K.; Xia, M. J. Org. Chem. 1998, 63, 9190. Iwao, M. Heterocycles 1994, 38, 45.
56. Bates, D.K.; Xia, M. J. Org. Chem. 1998, 63, 9190. Iwao, M. Heterocycles 1994, 38, 45.
57. Kaneko, T. J. Am. Chem. Soc. 1985, 107, 5490.
58. Kaneko, T.; Okamoto, Y.; Hatada, K. J. Chem. Soc., Chem. Commun. 1987, 1511.
59. Kita, Y.; Tamura, O.; Miki, T.; Tono, H.; Shibata, N.; Tamura, Y. Tetrahedron Lett. 1989, 30, 729.
60. Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimor, C.; Ohishi, H. J. Am. Chem. Soc. 1994, 116, 5116.
61. Carreño, M. C. Chem. Rev. 1995, 95, 1717. Kita, Y.; Shibata, N.; Yoshida, N.; Fujita, S. J. Chem. Soc., Perkin Trans. 1 1994, 3335.
62. Carreño, M. C. Chem. Rev. 1995, 95, 1717. Kita, Y.; Shibata, N.; Yoshida, N.; Fujita, S. J. Chem. Soc., Perkin Trans. 1 1994, 3335.
63. Kita, Y.; Shibata, N. Synlett 1996, 289.
64. Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K.; Fujita, S. J. Chem. Soc., Perkin Trans. 1 1995, 2405.
65. Kita, Y.; Shibata, N.; Kawano, N.; Tohjo, T.; Fujimori, C.; Matsumoto, K. Tetrahedron Lett. 1995, 36, 115.
66. Kita, Y.; Tamura, O.; Miki, T.; Tamura, Y. Tetrahedron Lett. 1987, 28, 6479.
67. Kita, Y.; Shibata, N.; Miki, T.; Takemura, Y.; Tamura, O. Chem. Pharm. Bull. 1992, 12.
68. Bennasar, M. L.; Zulaica, E.; Ramirez, A.; Bosch, J. J. Org. Chem. 1996, 61, 1239.
69. Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1993, 49, 11263.
70. Posner, G. H.; Asirvatham, E.; Ali, S. F. J. Chem. Soc., Chem. Commun. 1985, 542.
71. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Marino, J. P.; Perez, A. D. J. Am. Chem. Soc. 1984, 106, 7643.
72. Marino, J. P.; Neisser, M. J. Am. Chem. Soc. 1981, 103, 7687. Marino, J. P.; Perez, A. D. J. Am. Chem. Soc. 1984, 106, 7643.
73. Craig, D.; Daniels, K.; MacKenzie, A. R. Tetrahedron 1992, 48, 7803.
74. Padwa, A.; Kuethe, J. T. J. Org. Chem. 1998, 63, 4256. Kuethe, J. T.; Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 7082.
75. Padwa, A.; Kuethe, J. T. J. Org. Chem. 1998, 63, 4256. Kuethe, J. T.; Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 7082.
76. Ishibashi, H.; Harada, S.; Sato, K.; Ikeda, M.; Akai, S.; Tamura, Y. Chem. Pharm. Bull. 1985, 33, 5278.
77. Ishibashi, H.; Sato, K.; Ikeda, M. J. Chem. Soc., Perkin Trans. 1 1985, 605.
78. Hiemstra, H.; Speckamp, W. N. in Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp 1047-1082.
79. Ishibashi, H.; Sato, T.; Takahashi, M.; Hayashi, M.; Ikeda, M. Heterocycles 1988, 27, 2787.
80. Padwa, A. Chem. Commun. 1998, 1417.
81. Padwa, A.; Heidelbaugh, T. M.; Kuethe, J. T.; McClure, M. S. J. Org. Chem. 1998, 63, 6778.
82. Padwa, A.; Waterson, A. G. Tetrahedron Lett. 1998 39, 8585.
83. Kappe, C. O.; Murphree, S. S.; Padwa, A. Tetrahedron 1997, 53, 14179.
84. De Groot, A.; Jansen, B. J. M. J. Org. Chem. 1984, 49, 2034. Jansen, B. J. M.; Bouwman, C. T.; De Groot, A. Tetrahedron Lett. 1994, 35, 2977.
85. De Groot, A.; Jansen, B. J. M. J. Org. Chem. 1984, 49, 2034. Jansen, B. J. M.; Bouwman, C. T.; De Groot, A. Tetrahedron Lett. 1994, 35, 2977.
86. Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495. Padwa, A.; Coohran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706. Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 3938.
87. Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495. Padwa, A.; Coohran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706. Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 3938.
88. Cochran, J. E.; Padwa, A. Tetrahedron Lett. 1995, 36, 3495. Padwa, A.; Coohran, J. E.; Kappe, C. O. J. Org. Chem. 1996, 61, 3706. Cochran, J. E.; Padwa, A. J. Org. Chem. 1995, 60, 3938.
89. Padwa, A.; Kappe, C. O.; Cochran, J. E.; Snyder, J. P. J. Org. Chem. 1997, 62, 2786.
90. Friedrichsen, W. Adv. Heterocycl. Chem. 1980, 26, 135.
91. Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144.
92. Padwa, A.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1996, 61, 4888. Padwa, A.; Hennig, R.; Kappe, C. O.; Reger, T. S. J. Org. Chem. 1998, 63, 1144.
93. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976.
94. Jackson, A. H. In The Chemistry and Biology of Isoquinoline Alkaloids; Phillipson, J. D.; Roberts, M. F.; Zenk, M. H., Eds.; Springer: Berlin, 1985; p 62.
95. Tsuda, Y.; Hosai, S.; Nakai, A.; Sakai, Y.; Abe, T.; Ishi, Y.; Kiuchi, F.; Sano, T. Chem. Pharm. Bull. 1991, 39, 1365.
96. Kuethe, J.; Padwa, A. J. Org. Chem. 1997, 62, 774.
97. Osterhout, M.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123.
98. Kuethe, J. T.; Padwa, A. Tetrahedron Lett. 1997, 38, 1505.
99. Meyers, A. I.; Milot, G. J. Am. Chem. Soc. 1993, 115, 6652 and references cited therein.