A one-pot bicycloannulation method for the synthesis of tetrahydroisoquinoline systems

Journal of Organic Chemistry

Volumn 65, Issue 9, 2000, Pages 2684-2695

  Padwa, Albert ^a   Beall, L Scott ^a   Heidelbaugh, Todd M ^a   Liu, Bing ^a   Sheehan, Scott M ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; HETEROCYCLIC COMPOUND; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTALLIZATION; CYCLIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BICYCLO COMPOUNDS; ISOQUINOLINES; QUINOLIZINES; SPECTRUM ANALYSIS;

EID: 0034607674     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991742h     Document Type: Article

References (84)

1. Padwa, A. In 1,3-Dipolar Cycloaddition Chemistry; Wiley-Interscience: New York, 1984; Vois. 1 and 2.
2. Schoffstall, A. M.; Padwa, A. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, p 1.
3. Potts, K. T. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984.
4. Ohta, M.; Kato, H. In Nonbenzenoid Aromatics; Snyder, J. P., Ed.; Academic Press: New York, 1969; pp 117-248.
5. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 633.
6. Ollis, W. D.; Ramsden, C. A. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1976; Vol. 19, p 1. Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. Tetrahedron 1985, 41, 2239.
7. Ollis, W. D.; Ramsden, C. A. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Boulton, A. J., Eds.; Academic Press: New York, 1976; Vol. 19, p 1. Ollis, W. D.; Stanforth, S. P.; Ramsden, C. A. Tetrahedron 1985, 41, 2239.
8. Gingrich, H. L.; Baum, J. S. In The Chemistry of Heterocyclic Compounds. Vol. 45: Oxazoles; Turchi, I. J., Ed.; Wiley: New York, 1986; p 731.
9. Newton, C. G.; Ramsden, C. A. Tetrahedron 1982, 38, 2965.
10. Baker, W.; Ollis, W. D.; Poole, V. D. J. Chem. Soc. 1949, 307.
11. Baker, W.; Ollis, W. D.; Poole, V. D. J. Chem. Soc. 1950, 1542.
12. Osterhout, M. H.; Nadler, W. R.; Padwa, A. Synthesis 1994, 123.
13. Earl, J. C.; Mackney, A. W. J. Chem. Soc. 1935, 899.
14. Santiago; B.; Dalton, C. R.; Huber, E. W.; Kane, J. M. J. Org. Chem. 1995, 60, 4947.
15. Turchi, I. J. Ind. Eng. Chem. Prod. Res. Rev. 1980, 20, 32.
16. Turchi, I. J.; Dewar, M. J. S. Chem. Rev. 1975, 75, 389. Dewar, M. J. S.; Turchi, I. J. J. Chem. Soc., Perkin Trans. 2, 1976, 548.
17. Turchi, I. J.; Dewar, M. J. S. Chem. Rev. 1975, 75, 389. Dewar, M. J. S.; Turchi, I. J. J. Chem. Soc., Perkin Trans. 2, 1976, 548.
18. Hamaguchi, M.; Ibata, T. Tetrahedron Lett. 1974, 4475. Hamaguchi, M.; Ibata, T. Chem. Lett. 1975, 499.
19. Hamaguchi, M.; Ibata, T. Tetrahedron Lett. 1974, 4475. Hamaguchi, M.; Ibata, T. Chem. Lett. 1975, 499.
20. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
21. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
22. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
23. Padwa, A.; Marino, J. P., Jr.; Osterhout, M. H. J. Org. Chem. 1995, 60, 2704. Padwa, A.; Hertzog, D. L.; Nadler, W. R. J. Org. Chem. 1994, 59, 7072. Marino, J. P., Jr.; Osterhout, M. H.; Price, A. T.; Semones, M. A.; Padwa, A. J. Org. Chem. 1994, 59, 5518. Hertzog, D. L.; Austin, D. J.; Nadler, W. R.; Padwa, A. Tetrahedron Lett. 1992, 33, 4731.
24. Huisgen, R.; Gotthardt, H.; Bayer, H. O. Angew. Chem., Int. Ed. Engl. 1964, 3, 135. Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefer, F. C. Chem. Ber. 1970, 103, 2611.
25. Huisgen, R.; Gotthardt, H.; Bayer, H. O. Angew. Chem., Int. Ed. Engl. 1964, 3, 135. Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefer, F. C. Chem. Ber. 1970, 103, 2611.
26. Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223.
27. Potts, K. T.; Chen, S. J.; Kane, J.; Marshall, J. L. J. Org. Chem. 1977, 42, 1633.
28. Potts, K. T.; Houghton, E.; Singh, U. P. J. Org. Chem. 1974, 39, 3627. Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem. 1974, 39, 3631. Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem. 1976, 41, 818. Potts, K. T.; Baum, J.; Datta, S. K.; Houghton, E. J. Org. Chem. 1976, 41, 813.
29. Potts, K. T.; Houghton, E.; Singh, U. P. J. Org. Chem. 1974, 39, 3627. Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem. 1974, 39, 3631. Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem. 1976, 41, 818. Potts, K. T.; Baum, J.; Datta, S. K.; Houghton, E. J. Org. Chem. 1976, 41, 813.
30. Potts, K. T.; Houghton, E.; Singh, U. P. J. Org. Chem. 1974, 39, 3627. Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem. 1974, 39, 3631. Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem. 1976, 41, 818. Potts, K. T.; Baum, J.; Datta, S. K.; Houghton, E. J. Org. Chem. 1976, 41, 813.
31. Potts, K. T.; Houghton, E.; Singh, U. P. J. Org. Chem. 1974, 39, 3627. Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem. 1974, 39, 3631. Potts, K. T.; Baum, J.; Houghton, E. J. Org. Chem. 1976, 41, 818. Potts, K. T.; Baum, J.; Datta, S. K.; Houghton, E. J. Org. Chem. 1976, 41, 813.
32. Padwa, A.; Harring, S. R.; Hertzog, D. L.; Nadler, W. R. Synthesis 1994, 993.
33. Heidelbaugh, T. M.; Liu, B.; Padwa, A. Tetrahedron Lett. 1998, 39, 4757.
34. Baxter, E. W.; Marino, P. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer-Verlag: New York, 1992; Vol. 8, p 197.
35. Winterfeldt, E. Fortschr. Chem. Org. Naturst. 1974, 30, 469.
36. Döpke, W. The Alkaloids 1981, 20, 297.
37. Waldmann, H.; Braun, M.; Weymann, M.; Gewehr, M. Tetrahedron 1993, 49, 397. Lock, R.; Waldmann, H. Liebigs Ann. Chem. 1994, 511.
38. Waldmann, H.; Braun, M.; Weymann, M.; Gewehr, M. Tetrahedron 1993, 49, 397. Lock, R.; Waldmann, H. Liebigs Ann. Chem. 1994, 511.
39. Kuehne, M. E.; Muth, R. S. J. Org. Chem. 1991, 56, 2701.
40. Martin, S. F.; Grzejszczak, S.; Ruger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072; 1987, 109, 6124.
41. Martin, S. F.; Grzejszczak, S.; Ruger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072; 1987, 109, 6124.
42. Stork, G. Pure Appl. Chem. 1989, 51, 439.
43. Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157; Heterocycles 1987, 25, 263.
44. Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157; Heterocycles 1987, 25, 263.
45. Baxter, E. W.; Labaree, D.; Ammon, H. L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 7682.
46. Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6398, 6404. Miyata, O.; Hirata, Y.; Naifo, T.; Ninomiya, I. Heterocycles 1984, 22, 1041.
47. Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6398, 6404. Miyata, O.; Hirata, Y.; Naifo, T.; Ninomiya, I. Heterocycles 1984, 22, 1041.
48. Wenkert, E.; Chang, C. J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. J. Am. Chem. Soc. 1976, 98, 3645.
49. Claus, R. E.; Schreiber, S. L. Organic Syntheses; Wiley: New York, 1990; Collect. Vol. VII, p 168.
50. Snider, B. B.; Kulkarni, Y. S. J. Org. Chem. 1987, 52, 307.
51. Padwa, A.; Hertzog, D. L.; Nadler, W. R.; Osterhout, M. H.; Price, A. T. J. Org. Chem. 1994, 59, 1418.
52. Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. Ho, K. M.; Lam, C. H.; Luh, T. Y. J. Org. Chem. 1989, 54, 4474. Alper, H.; Blais, C. J. Chem. Soc., Chem. Commun. 1980, 169. Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356.
53. Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. Ho, K. M.; Lam, C. H.; Luh, T. Y. J. Org. Chem. 1989, 54, 4474. Alper, H.; Blais, C. J. Chem. Soc., Chem. Commun. 1980, 169. Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356.
54. Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. Ho, K. M.; Lam, C. H.; Luh, T. Y. J. Org. Chem. 1989, 54, 4474. Alper, H.; Blais, C. J. Chem. Soc., Chem. Commun. 1980, 169. Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356.
55. Luh, T. Y.; Ni, Z. J. Synthesis 1990, 89. Ho, K. M.; Lam, C. H.; Luh, T. Y. J. Org. Chem. 1989, 54, 4474. Alper, H.; Blais, C. J. Chem. Soc., Chem. Commun. 1980, 169. Pettit, G. R.; van Tamelen, E. E. Org. React. 1962, 12, 356.
56. Gutierrez, C. G.; Summerhays, L. R. J. Org. Chem. 1984, 49, 5206.
57. The relative stereochemistry drawn is assumed and is primarily based on the fact that the cis-ring junction is lower in energy according to molecular mechanics calculations.
58. Sheehan, S. M.; Beall, L. S.; Padwa, A. Tetrahedron Lett. 1998, 39, 4761.
59. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. Hart, D. J. In Alkaloids; Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1988; Vol. 6, p 227.
60. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. Hart, D. J. In Alkaloids; Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1988; Vol. 6, p 227.
61. Hiemstra, H.; Speckamp, W. N. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 2, p 1047. Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1988; Vol. 32, p 271. Hart, D. J. In Alkaloids; Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1988; Vol. 6, p 227.
62. Kametani, T.; Fukumoto, K. The Chemistry of Heterocyclic Compounds, Isoquinoline Part 1; Grethe, G., Ed.; Wiley: New York; p 170. Jones, G. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, p 438.
63. Kametani, T.; Fukumoto, K. The Chemistry of Heterocyclic Compounds, Isoquinoline Part 1; Grethe, G., Ed.; Wiley: New York; p 170. Jones, G. Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: Oxford, 1984; Vol. 2, p 438.
64. For some examples involving 4 + 2-cycloaddition across an indolo π-bond, see: Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Padwa, A.; Price, A. T. J. Org. Chem. 1998, 63, 556. Benson, S. C.; Lee, L.; Snyder, J. K. Tetrahedron Lett. 1996, 37, 5061. Wan, Z. K.; Snyder, J. K. Tetrahedron Lett. 1998, 39, 2487.
65. For some examples involving 4 + 2-cycloaddition across an indolo π-bond, see: Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Padwa, A.; Price, A. T. J. Org. Chem. 1998, 63, 556. Benson, S. C.; Lee, L.; Snyder, J. K. Tetrahedron Lett. 1996, 37, 5061. Wan, Z. K.; Snyder, J. K. Tetrahedron Lett. 1998, 39, 2487.
66. For some examples involving 4 + 2-cycloaddition across an indolo π-bond, see: Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Padwa, A.; Price, A. T. J. Org. Chem. 1998, 63, 556. Benson, S. C.; Lee, L.; Snyder, J. K. Tetrahedron Lett. 1996, 37, 5061. Wan, Z. K.; Snyder, J. K. Tetrahedron Lett. 1998, 39, 2487.
67. For some examples involving 4 + 2-cycloaddition across an indolo π-bond, see: Dehaen, W.; Hassner, A. J. Org. Chem. 1991, 56, 896. Padwa, A.; Price, A. T. J. Org. Chem. 1998, 63, 556. Benson, S. C.; Lee, L.; Snyder, J. K. Tetrahedron Lett. 1996, 37, 5061. Wan, Z. K.; Snyder, J. K. Tetrahedron Lett. 1998, 39, 2487.
68. Lounasmaa, M.; Tolvanen, A. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1992; Vol. 42, p 1. Taylor, W. I. The Alkaloids 1968, 11, 125.
69. Lounasmaa, M.; Tolvanen, A. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: New York, 1992; Vol. 42, p 1. Taylor, W. I. The Alkaloids 1968, 11, 125.
70. Padwa, A.; Gunn, D. E.; Osterhout, M. H. Synthesis 1997, 1353.
71. Shamma, M. The Isoquinoline Alkaloids; Academic Press: New York, 1978. Lundstrom, J. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1983; Vol. 21, p 255.
72. Shamma, M. The Isoquinoline Alkaloids; Academic Press: New York, 1978. Lundstrom, J. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1983; Vol. 21, p 255.
73. Speckamp, W. N.; Hiemstra, H. Tetrahedron 1985, 41, 4367.
74. Kitamura, M.; Hsiao, Y.; Ohta, M.; Tsukamoto, M.; Ohta, T.; Takaya, H.; Noyori, R. J. Org. Chem. 1994, 59, 297.
75. Mondon, A.; Hansen, K. F.; Boehme, K.; Faro, H. P.; Nestler, H. J.; Vilhuber, H. G.; Böttcher, K. Chem. Ber. 1970, 103, 615. Mondon, A.; Seidel, P. R. Chem. Ber. 1971, 104, 2937. Mondon, A.; Nestler, H. J. Chem. Ber. 1979, 112, 1329.
76. Mondon, A.; Hansen, K. F.; Boehme, K.; Faro, H. P.; Nestler, H. J.; Vilhuber, H. G.; Böttcher, K. Chem. Ber. 1970, 103, 615. Mondon, A.; Seidel, P. R. Chem. Ber. 1971, 104, 2937. Mondon, A.; Nestler, H. J. Chem. Ber. 1979, 112, 1329.
77. Mondon, A.; Hansen, K. F.; Boehme, K.; Faro, H. P.; Nestler, H. J.; Vilhuber, H. G.; Böttcher, K. Chem. Ber. 1970, 103, 615. Mondon, A.; Seidel, P. R. Chem. Ber. 1971, 104, 2937. Mondon, A.; Nestler, H. J. Chem. Ber. 1979, 112, 1329.
78. Zhang, Z. J.; Padwa, A. Heterocycles 1994, 37, 41.
79. Abramovitch, R. A. J. Chem. Soc. 1956, 4589.
80. Yamaguchi, R.; Hamasaki, T.; Sasaki, T.; Ohta, T.; Utimoto, K.; Kozima, S.; Takaya, H. J. Org. Chem. 1993, 58, 1136.
81. Padwa, A.; Coats, S. J.; Harring, S. R.; Hadjiarapoglu, L.; Semones, M. A. Synthesis 1995, 8, 973.
82. Castedo, L.; Marcos, C. F.; Monteagudo, M.; Tojo, G. Synth. Commun. 1992, 22, 677.
83. Hua, D. H.; Miao, S. W.; Bharathi, S. N.; Katsuhira, T.; Bravo, A. A. J. Org. Chem. 1990, 55, 3682.
84. Yates, P. C.; McCall, C. J.; Stevens, M. F. G. Tetrahedron 1991, 47, 6493.