Chemistry of Azulenequinones and Their Analogues

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 5, 1996, Pages 1149-1178

  Nozoe, Tetsuo ^a,c,d,e,f   Takeshita, Hitoshi ^b  

^a KAO CORPORATION   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

^d Government General's Laboratories   (Japan)

^e NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^f OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0005814847     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1149     Document Type: Article

References (136)

1. 1a) Chap. 24, pp. 1385-1988 d) T. Nozoe, "Seventy Years in Organic Chemistry," in "Profiles, Pathways and Dreams," ed by J. I. Seeman, American Chemical Society, Washington DC (1991), pp. 91-100, pp. 160-171 e) Y. Matsubara, H. Yamamoto, and T. Nozoe, "Oxidation Products of Guaiazulene and Other Azulenic Hydrocarbons," in "Studies in Natural Products Chemistry," ed by Atta-ur-Rahman, Elsevier, Amsterdam (1994), Vol. 14, pp. 313-354 f) An extensive review on azulene syntheses see: K.-P. Zeller, "Azulene," "Carbo-cyclische π-Electron System," (Houben-Weyl), in "Methoden der Organischen Chemie, V/2c," Georg Thieme, Stuttgart (1985), pp. 127-418.
2. 1a) Chap. 24, pp. 1385-1988 d) T. Nozoe, "Seventy Years in Organic Chemistry," in "Profiles, Pathways and Dreams," ed by J. I. Seeman, American Chemical Society, Washington DC (1991), pp. 91-100, pp. 160-171 e) Y. Matsubara, H. Yamamoto, and T. Nozoe, "Oxidation Products of Guaiazulene and Other Azulenic Hydrocarbons," in "Studies in Natural Products Chemistry," ed by Atta-ur-Rahman, Elsevier, Amsterdam (1994), Vol. 14, pp. 313-354 f) An extensive review on azulene syntheses see: K.-P. Zeller, "Azulene," "Carbo-cyclische π-Electron System," (Houben-Weyl), in "Methoden der Organischen Chemie, V/2c," Georg Thieme, Stuttgart (1985), pp. 127-418.
3. 1a) Chap. 24, pp. 1385-1988 d) T. Nozoe, "Seventy Years in Organic Chemistry," in "Profiles, Pathways and Dreams," ed by J. I. Seeman, American Chemical Society, Washington DC (1991), pp. 91-100, pp. 160-171 e) Y. Matsubara, H. Yamamoto, and T. Nozoe, "Oxidation Products of Guaiazulene and Other Azulenic Hydrocarbons," in "Studies in Natural Products Chemistry," ed by Atta-ur-Rahman, Elsevier, Amsterdam (1994), Vol. 14, pp. 313-354 f) An extensive review on azulene syntheses see: K.-P. Zeller, "Azulene," "Carbo-cyclische π-Electron System," (Houben-Weyl), in "Methoden der Organischen Chemie, V/2c," Georg Thieme, Stuttgart (1985), pp. 127-418.
4. 1a) Chap. 24, pp. 1385-1988 d) T. Nozoe, "Seventy Years in Organic Chemistry," in "Profiles, Pathways and Dreams," ed by J. I. Seeman, American Chemical Society, Washington DC (1991), pp. 91-100, pp. 160-171 e) Y. Matsubara, H. Yamamoto, and T. Nozoe, "Oxidation Products of Guaiazulene and Other Azulenic Hydrocarbons," in "Studies in Natural Products Chemistry," ed by Atta-ur-Rahman, Elsevier, Amsterdam (1994), Vol. 14, pp. 313-354 f) An extensive review on azulene syntheses see: K.-P. Zeller, "Azulene," "Carbo-cyclische π-Electron System," (Houben-Weyl), in "Methoden der Organischen Chemie, V/2c," Georg Thieme, Stuttgart (1985), pp. 127-418.
5. 1a) Chap. 24, pp. 1385-1988 d) T. Nozoe, "Seventy Years in Organic Chemistry," in "Profiles, Pathways and Dreams," ed by J. I. Seeman, American Chemical Society, Washington DC (1991), pp. 91-100, pp. 160-171 e) Y. Matsubara, H. Yamamoto, and T. Nozoe, "Oxidation Products of Guaiazulene and Other Azulenic Hydrocarbons," in "Studies in Natural Products Chemistry," ed by Atta-ur-Rahman, Elsevier, Amsterdam (1994), Vol. 14, pp. 313-354 f) An extensive review on azulene syntheses see: K.-P. Zeller, "Azulene," "Carbo-cyclische π-Electron System," (Houben-Weyl), in "Methoden der Organischen Chemie, V/2c," Georg Thieme, Stuttgart (1985), pp. 127-418.
6. 1a) Chap. 24, pp. 1385-1988 d) T. Nozoe, "Seventy Years in Organic Chemistry," in "Profiles, Pathways and Dreams," ed by J. I. Seeman, American Chemical Society, Washington DC (1991), pp. 91-100, pp. 160-171 e) Y. Matsubara, H. Yamamoto, and T. Nozoe, "Oxidation Products of Guaiazulene and Other Azulenic Hydrocarbons," in "Studies in Natural Products Chemistry," ed by Atta-ur-Rahman, Elsevier, Amsterdam (1994), Vol. 14, pp. 313-354 f) An extensive review on azulene syntheses see: K.-P. Zeller, "Azulene," "Carbo-cyclische π-Electron System," (Houben-Weyl), in "Methoden der Organischen Chemie, V/2c," Georg Thieme, Stuttgart (1985), pp. 127-418.
7. L. T. Scott, M. D. Rozeboom, K. N. Houk, T. Fukunaga, H. J. Lindner, and K. Hafner, J. Am. Chem. Soc., 102, 5169 (1980).
8. K. Hafner, K. H. Vöpel, G. Ploss, and C. König, Justus Liebigs Ann. Chem., 661, 52 (1963).
9. a) A. Marsili and M. Isola, Tetrahedron, 23, 1037 (1967)
10. b) W. Ried and J. Ehret, Angew. Chem., 80, 365 (1968); Angew. Chem., Int. Ed. Engl., 7, 737 (1968).
11. b) W. Ried and J. Ehret, Angew. Chem., 80, 365 (1968); Angew. Chem., Int. Ed. Engl., 7, 737 (1968).
12. a) Unpublished results of T. Nozoe et al., see: M. Ando, M.Sc. Thesis, Tohoku University, Sendai, 1967, Abstr., p. 13
13. b) T. Nozoe, T. Asao, H. Susumago, and M. Ando, Bull. Chem. Soc. Jpn., 47, 1471 (1974)
14. 5a)).
15. Nozoe Azulene Synthesis: see for example: a) T. Nozoe, K. Takase, and N. Shimazaki, Bull. Chem. Soc. Jpn., 37, 1640 (1964) b) T. Nozoe, S. Seto, K. Takase, S. Matsumura, and T. Nakazawa, Nippon Kagaku Zasshi, 86, 346 (1965) c) M. Tada, Bull. Chem. Soc. Jpn., 39, 1954 (1966) d) T. Nozoe, K. Takase, T. Nakazawa, and S. Fukuda, Tetrahedron, 27, 3357 (1971) e) T. Nozoe, K. Takase, M. Kato, and T. Nogi, Tetrahedron, 27, 6023 (1971) f) T. Nozoe, T. Asao, and M. Oda, Bull. Chem. Soc. Jpn., 47, 681 (1974) g) T. Nozoe, Pure Appl. Chem., 28, 239 (1971).
16. Nozoe Azulene Synthesis: see for example: a) T. Nozoe, K. Takase, and N. Shimazaki, Bull. Chem. Soc. Jpn., 37, 1640 (1964) b) T. Nozoe, S. Seto, K. Takase, S. Matsumura, and T. Nakazawa, Nippon Kagaku Zasshi, 86, 346 (1965) c) M. Tada, Bull. Chem. Soc. Jpn., 39, 1954 (1966) d) T. Nozoe, K. Takase, T. Nakazawa, and S. Fukuda, Tetrahedron, 27, 3357 (1971) e) T. Nozoe, K. Takase, M. Kato, and T. Nogi, Tetrahedron, 27, 6023 (1971) f) T. Nozoe, T. Asao, and M. Oda, Bull. Chem. Soc. Jpn., 47, 681 (1974) g) T. Nozoe, Pure Appl. Chem., 28, 239 (1971).
17. Nozoe Azulene Synthesis: see for example: a) T. Nozoe, K. Takase, and N. Shimazaki, Bull. Chem. Soc. Jpn., 37, 1640 (1964) b) T. Nozoe, S. Seto, K. Takase, S. Matsumura, and T. Nakazawa, Nippon Kagaku Zasshi, 86, 346 (1965) c) M. Tada, Bull. Chem. Soc. Jpn., 39, 1954 (1966) d) T. Nozoe, K. Takase, T. Nakazawa, and S. Fukuda, Tetrahedron, 27, 3357 (1971) e) T. Nozoe, K. Takase, M. Kato, and T. Nogi, Tetrahedron, 27, 6023 (1971) f) T. Nozoe, T. Asao, and M. Oda, Bull. Chem. Soc. Jpn., 47, 681 (1974) g) T. Nozoe, Pure Appl. Chem., 28, 239 (1971).
18. Nozoe Azulene Synthesis: see for example: a) T. Nozoe, K. Takase, and N. Shimazaki, Bull. Chem. Soc. Jpn., 37, 1640 (1964) b) T. Nozoe, S. Seto, K. Takase, S. Matsumura, and T. Nakazawa, Nippon Kagaku Zasshi, 86, 346 (1965) c) M. Tada, Bull. Chem. Soc. Jpn., 39, 1954 (1966) d) T. Nozoe, K. Takase, T. Nakazawa, and S. Fukuda, Tetrahedron, 27, 3357 (1971) e) T. Nozoe, K. Takase, M. Kato, and T. Nogi, Tetrahedron, 27, 6023 (1971) f) T. Nozoe, T. Asao, and M. Oda, Bull. Chem. Soc. Jpn., 47, 681 (1974) g) T. Nozoe, Pure Appl. Chem., 28, 239 (1971).
19. Nozoe Azulene Synthesis: see for example: a) T. Nozoe, K. Takase, and N. Shimazaki, Bull. Chem. Soc. Jpn., 37, 1640 (1964) b) T. Nozoe, S. Seto, K. Takase, S. Matsumura, and T. Nakazawa, Nippon Kagaku Zasshi, 86, 346 (1965) c) M. Tada, Bull. Chem. Soc. Jpn., 39, 1954 (1966) d) T. Nozoe, K. Takase, T. Nakazawa, and S. Fukuda, Tetrahedron, 27, 3357 (1971) e) T. Nozoe, K. Takase, M. Kato, and T. Nogi, Tetrahedron, 27, 6023 (1971) f) T. Nozoe, T. Asao, and M. Oda, Bull. Chem. Soc. Jpn., 47, 681 (1974) g) T. Nozoe, Pure Appl. Chem., 28, 239 (1971).
20. Nozoe Azulene Synthesis: see for example: a) T. Nozoe, K. Takase, and N. Shimazaki, Bull. Chem. Soc. Jpn., 37, 1640 (1964) b) T. Nozoe, S. Seto, K. Takase, S. Matsumura, and T. Nakazawa, Nippon Kagaku Zasshi, 86, 346 (1965) c) M. Tada, Bull. Chem. Soc. Jpn., 39, 1954 (1966) d) T. Nozoe, K. Takase, T. Nakazawa, and S. Fukuda, Tetrahedron, 27, 3357 (1971) e) T. Nozoe, K. Takase, M. Kato, and T. Nogi, Tetrahedron, 27, 6023 (1971) f) T. Nozoe, T. Asao, and M. Oda, Bull. Chem. Soc. Jpn., 47, 681 (1974) g) T. Nozoe, Pure Appl. Chem., 28, 239 (1971).
21. Nozoe Azulene Synthesis: see for example: a) T. Nozoe, K. Takase, and N. Shimazaki, Bull. Chem. Soc. Jpn., 37, 1640 (1964) b) T. Nozoe, S. Seto, K. Takase, S. Matsumura, and T. Nakazawa, Nippon Kagaku Zasshi, 86, 346 (1965) c) M. Tada, Bull. Chem. Soc. Jpn., 39, 1954 (1966) d) T. Nozoe, K. Takase, T. Nakazawa, and S. Fukuda, Tetrahedron, 27, 3357 (1971) e) T. Nozoe, K. Takase, M. Kato, and T. Nogi, Tetrahedron, 27, 6023 (1971) f) T. Nozoe, T. Asao, and M. Oda, Bull. Chem. Soc. Jpn., 47, 681 (1974) g) T. Nozoe, Pure Appl. Chem., 28, 239 (1971).
22. a) S. Kosuge, T. Morita, and K. Takase, Chem. Lett., 1975, 733
23. b) T. Morita and K. Takase, Chem. Lett., 1977, 513.
24. T. Morita, M. Karasawa, and K. Takase, Chem. Lett., 1980, 197.
25. T. Morita, F. Ise, and K. Takase, Chem. Lett., 1982, 1303.
26. a) T. Morita, F. Ise, and K. Takase, Chem. Lett., 1981, 1661
27. b) T. Morita, K. Hirose, and K. Takase, Formosan Sci., 45, 95 (1992).
28. a) T. Nozoe, S. Takekuma, M. Doi, Y. Matsubara, and H. Yamamoto, Chem. Lett., 1984, 627
29. b) Y. Matsubara, S. Takekuma, K. Yokoi, H. Yamamoto, and T. Nozoe, Chem. Lett., 1984, 631
30. c) Y. Matsubara, S. Takekuma, K. Yokoi, H. Yamamoto, and T. Nozoe, Bull. Chem. Soc. Jpn., 60, 1415 (1987)
31. d) Y. Matsubara. S. Takekuma, H. Yamamoto, and T. Nozoe, Chem. Lett., 1987, 455
32. e) S. Takekuma, Y. Matsubara, H. Yamamoto, and T. Nozoe, Bull. Chem. Soc. Jpn., 61, 475 (1988).
33. a) Y. Matsubara, S. Matsui, S. Takekuma, H. Yamamoto, and T. Nozoe, Nippon Kagaku Kaishi, 1988, 1704
34. b) Y. Matsubara, S. Matsui, S. Takekuma, Y.-P. Quo, H. Yamamoto, and T. Nozoe, Bull. Chem. Soc. Jpn., 62, 2040 (1989)
35. c) Y. Matsubara, M. Morita, S. Matsui, S. Takekuma, H. Yamamoto, S. Itô, N. Morita, T. Asao, and T. Nozoe, Bull. Chem. Soc. Jpn., 63, 1841 (1990)
36. d) H. Takekuma, S. Takekuma, Y. Matsubara, H. Yamamoto, and T. Nozoe, Chem. Lett., 1995, 465
37. e) H. Takekuma, S. Takekuma, D. Makihara, Y. Matsubara, H. Yamamoto, and T. Nozoe, Nippon Kagaku Kaishi, 1995, 567
38. f) Y. Matsubara, M. Morita, S. Takekuma, T. Nakano, H. Yamamoto, and T. Nozoe, Bull. Chem. Soc. Jpn., 64, 3497 (1991)
39. g) Y. Matsubara, S. Takekuma, H. Yamamoto, and T. Nozoe, presented at "the 7th International Symposium on the Chemistry of Novel Aromatic Compounds," Victoria, Canada, July 1992, Abstr., p. 104.
40. a) R. A. Fallahpour, R. Sigrist, and H.-J. Hansen, Helv. Chim. Acta, 78, 1408 (1995)
41. b) C.-P. Wu, J.-L. Jeo, P.-W. Yang, and T. Nozoe, Formosan Sci., 48, 81 (1995).
42. a) B. Alpertunga, S. Imre, H. J. Cowe, P. J. Cox, and R. H. Thomson, Tetrahedron Lett., 1983, 4461
43. b) V. Yu. Bagirov, V. I. Sheichenko, R. Yu. Gasanova, and M. G. Pimenov, Khim. Prir. Soedin, 1978, 811
44. c) W. Schüep, J. F. Blount, T. H. Williams, and A. Stempel, J. Antibiot., 31, 1226 (1978).
45. a) L. T. Scott, Pure Appl. Chem., 55, 363 (1983)
46. b) L. T. Scott, M. A. Minton, and M. A. Kirms, J. Am. Chem. Soc., 102, 6311 (1980)
47. c) L. T. Scott et al., unpublished.
48. a) L. T. Scott, P. Grütter, and R. E. Chamberlain, III, J. Am. Chem. Soc., 106, 4852 (1984)
49. b) L. T. Scott and C. M. Adams, J. Am. Chem. Soc., 106, 4857 (1984).
50. a) M. K. W. Li and P. J. Scheuer, Tetrahedron Lett., 1984, 587
51. b) M. K. W. Li, PhD Dissertation, University of Hawaii, (1985)
52. c) private communication from Professor P. J. Scheuer.
53. a) T. Nozoe, S. Ishikawa, and K. Shindo, Chem. Lett., 1989, 353
54. b) T. Nozoe, K. Shindo, H. Wakabayashi, T. Kurihara, and S. Ishikawa, Collect. Czech. Chem. Commun., 56, 991 (1991)
55. c) K. Shindo and T. Nozoe, unpublished result.
56. a) K. Shindo, H. Wakabayashi, S. Ishikawa, and T. Nozoe, presented at "the 9th Symposium on the Fundamental Organic Chemistry," Hiroshima, Oct. 1989, Abstr., p. 809
57. b) T. Nozoe, and K. Shindo et al., to be published.
58. a) H. Wakabayashi, K. Shindo, S. Ishikawa, and T. Nozoe, presented at "the 65th National Meeting of the Chemical Society of Japan," Tokyo, March 1993, Abstr., No. 1A717
59. b) T. Nozoe, presented at "the 24th Symposium on Structural Organic Chemistry," Kiryu, Oct. 1993, Abstr., No. 1A07
60. c) T. Kurihara, S. Ishikawa, and T. Nozoe, presented at "the 24th Symposium on Structural Organic Chemistry," Kiryu, Oct. 1993, Abstr., No. P-04
61. d) T. Suzuki, T. Kurihara, H. Wakabayashi, K. Shindo, T. Miyashi, M. Yasunami, and T. Nozoe, to be published.
62. a) T. Nozoe, H. Wakabayashi, K. Shindo, and M. Kageyama, presented at "the 65th Symposium on Synthetic Organic Chemistry," Tokyo, Jun. 1994, Abstr., pp. 21-24
63. b) T. Nozoe, presented at "the 4th Towa University International Symposium," Fukuoka, Nov. 1994, Abstr., pp. 13-18
64. c) T. Nozoe, H. Wakabayashi, K. Shindo, P.-W. Yang, and M. Yasunami, presented at "the 8th International Symposium on Novel Aromatic Compounds," Braunschweig, Germany, Aug. 1995, Abstr., p. 85.
65. a) A. G. Anderson, Jr., R. Scotoni, Jr., E. J. Cowles, and C. G. Fritz, J. Org. Chem., 22, 1193 (1957)
66. b) A. G. Anderson, Jr., and L. L. Replogle, J. Org. Chem., 25, 1275 (1960)
67. c) K. Hafner, A. Stephan, and C. Bernhard, Justus Liebigs Ann. Chem., 650, 42 (1961)
68. d) K. Hafner and K. L. Moritz, Justus Liebigs Ann. Chem., 656, 40 (1962).
69. a) T. Nozoe, H. Wakabayashi, K. Shindo, T. Kurihara, S. Ishikawa, and M. Kageyama, Chem. Lett., 1995, 25
70. b) T. Nozoe, H. Wakabayashi, K. Shindo, S. Ishikawa, and M. Kageyama, to be submitted.
71. Azulene synthesis by enamine method, see: a) P.-W. Yang, M. Yasunami, and K. Takase, Tetrahedron Lett., 1971, 4275 b) A. Chen, M. Yasunami, and K. Takase, Tetrahedron Lett., 1974, 2581 c) K. Takase and M. Yasunami, Yuki Gosei Kagaku Kyokai Shi, 39, 1172 (1981) d) M. Yasunami, S. Miyoshi, N. Kanegae, and K. Takase, Bull. Chem. Soc. Jpn., 66, 892 (1993).
72. Azulene synthesis by enamine method, see: a) P.-W. Yang, M. Yasunami, and K. Takase, Tetrahedron Lett., 1971, 4275 b) A. Chen, M. Yasunami, and K. Takase, Tetrahedron Lett., 1974, 2581 c) K. Takase and M. Yasunami, Yuki Gosei Kagaku Kyokai Shi, 39, 1172 (1981) d) M. Yasunami, S. Miyoshi, N. Kanegae, and K. Takase, Bull. Chem. Soc. Jpn., 66, 892 (1993).
73. Azulene synthesis by enamine method, see: a) P.-W. Yang, M. Yasunami, and K. Takase, Tetrahedron Lett., 1971, 4275 b) A. Chen, M. Yasunami, and K. Takase, Tetrahedron Lett., 1974, 2581 c) K. Takase and M. Yasunami, Yuki Gosei Kagaku Kyokai Shi, 39, 1172 (1981) d) M. Yasunami, S. Miyoshi, N. Kanegae, and K. Takase, Bull. Chem. Soc. Jpn., 66, 892 (1993).
74. Azulene synthesis by enamine method, see: a) P.-W. Yang, M. Yasunami, and K. Takase, Tetrahedron Lett., 1971, 4275 b) A. Chen, M. Yasunami, and K. Takase, Tetrahedron Lett., 1974, 2581 c) K. Takase and M. Yasunami, Yuki Gosei Kagaku Kyokai Shi, 39, 1172 (1981) d) M. Yasunami, S. Miyoshi, N. Kanegae, and K. Takase, Bull. Chem. Soc. Jpn., 66, 892 (1993).
75. Azulene synthesis with vinyl-ether type reagent, see: a) T. Nozoe, P.-W. Yang, C.-P. Wu, T.-S. Huang, T.-H. Lee, H. Okai, H. Wakabayashi, and S. Ishikawa, Heterocycles, 29, 1225 (1989) b) T. Nozoe, H. Wakabayashi, S. Ishikawa, C.-P. Wu, and P.-W. Yang, Heterocycles, 31, 17 (1990) c) T. Nozoe, H. Wakabayashi, K. Shindo, S. Ishikawa, C.-P. Wu, and P.-W. Yang, Heterocycles, 32, 213 (1991) d) H. Wakabayashi, P.-W. Yang, C.-P. Wu, K. Shindo, S. Ishikawa, and T. Nozoe, Heterocycles, 34, 429 (1992).
76. Azulene synthesis with vinyl-ether type reagent, see: a) T. Nozoe, P.-W. Yang, C.-P. Wu, T.-S. Huang, T.-H. Lee, H. Okai, H. Wakabayashi, and S. Ishikawa, Heterocycles, 29, 1225 (1989) b) T. Nozoe, H. Wakabayashi, S. Ishikawa, C.-P. Wu, and P.-W. Yang, Heterocycles, 31, 17 (1990) c) T. Nozoe, H. Wakabayashi, K. Shindo, S. Ishikawa, C.-P. Wu, and P.-W. Yang, Heterocycles, 32, 213 (1991) d) H. Wakabayashi, P.-W. Yang, C.-P. Wu, K. Shindo, S. Ishikawa, and T. Nozoe, Heterocycles, 34, 429 (1992).
77. Azulene synthesis with vinyl-ether type reagent, see: a) T. Nozoe, P.-W. Yang, C.-P. Wu, T.-S. Huang, T.-H. Lee, H. Okai, H. Wakabayashi, and S. Ishikawa, Heterocycles, 29, 1225 (1989) b) T. Nozoe, H. Wakabayashi, S. Ishikawa, C.-P. Wu, and P.-W. Yang, Heterocycles, 31, 17 (1990) c) T. Nozoe, H. Wakabayashi, K. Shindo, S. Ishikawa, C.-P. Wu, and P.-W. Yang, Heterocycles, 32, 213 (1991) d) H. Wakabayashi, P.-W. Yang, C.-P. Wu, K. Shindo, S. Ishikawa, and T. Nozoe, Heterocycles, 34, 429 (1992).
78. Azulene synthesis with vinyl-ether type reagent, see: a) T. Nozoe, P.-W. Yang, C.-P. Wu, T.-S. Huang, T.-H. Lee, H. Okai, H. Wakabayashi, and S. Ishikawa, Heterocycles, 29, 1225 (1989) b) T. Nozoe, H. Wakabayashi, S. Ishikawa, C.-P. Wu, and P.-W. Yang, Heterocycles, 31, 17 (1990) c) T. Nozoe, H. Wakabayashi, K. Shindo, S. Ishikawa, C.-P. Wu, and P.-W. Yang, Heterocycles, 32, 213 (1991) d) H. Wakabayashi, P.-W. Yang, C.-P. Wu, K. Shindo, S. Ishikawa, and T. Nozoe, Heterocycles, 34, 429 (1992).
79. a) T. Nozoe, H. Wakabayashi, K. Shindo, and M. Yasunami, Chem. Lett., 1995, 439
80. b) H. Wakabayashi, K. Shindo, M. Yasunami, and T. Nozoe, to be published.
81. a) T. Nozoe, H. Wakabayashi, A. Takano, K. Shindo, M. Yasunami, J.-A. Chen, and P.-W. Yang, manuscript in preparation
82. b) T. Nozoe, H. Wakabayashi, and K. Hafner, to be published.
83. a) T. Nozoe, K. Shindo, H. Wakabayashi, T. Kurihara, and J. Uzawa, Chem. Lett., 1995, 687
84. b) Crystal structure of compound 170 was measured by Dr. C. Kabuto (Tohoku Univ.)
85. c) K. Shindo, H. Wakabayashi, T. Kurihara, J. Uzawa, and T. Nozoe, Bull. Chem. Soc. Jpn., to be published
86. d) T. Nozoe, Y. Ikeda, and H. Takeshita, to be published.
87. a) T. Nozoe, H. Wakabayashi, K. Shindo, M. Yasunami, J.-A. Chen, and P.-W. Yang, in preparation
88. b) K. Fujimori, M. Yasunami, and T. Nozoe, unpublished results
89. c) T. Nozoe, H. Wakabayashi, and M. Yasunami, in preparation.
90. O. Sato, A. Takahashi, S. Yoshioka, J. Tsunetsugu, and T. Nozoe, Bull. Chem. Soc. Jpn., to be published.
91. K. Fujimori, H. Matsuo, M. Yasunami, and T. Nozoe, Heterocycles, submitted.
92. a) T. Nozoe, H. Wakabayashi, K. Shindo, and S. Ishikawa, Chem. Lett., 1995, 27
93. b) suggestion by Professor J. A. Berson of Yale Univ.
94. T. Suzuki, H. Wakabayashi, and T. Nozoe, unpublished results.
95. H. Takekuma, S. Takekuma, Y. Matsubara, H. Yamamoto, and T. Nozoe, Chem. Lett., 1995, 465; X-Ray was kindly measured by Messers. J. Okada and O. Yamashita (Tochigi Labs., Kao Corp.).
96. T. Nozoe, H. Wakabayashi, and C. Kabuto, to be published.
97. In respect of the CH⋯O, CH⋯Cl, C⋯O, weak interactions, see the following references: a) R. Taylor and O. Kennard, J. Am. Chem. Soc., 104, 5063 (1982) b) G. R. Desiraju, Acc. Chem. Res., 24, 290 (1991) c) T. Bernstein, M. D. Coben, and L. L. Witz, "The Chemistry of Quinonoid Compounds," ed by S. Patai, Interscience, New York (1974), p. 37 d) P. Murray-Rust and W. D. S. Motherwell, J. Am. Chem. Soc., 101, 4374 (1979).
98. In respect of the CH⋯O, CH⋯Cl, C⋯O, weak interactions, see the following references: a) R. Taylor and O. Kennard, J. Am. Chem. Soc., 104, 5063 (1982) b) G. R. Desiraju, Acc. Chem. Res., 24, 290 (1991) c) T. Bernstein, M. D. Coben, and L. L. Witz, "The Chemistry of Quinonoid Compounds," ed by S. Patai, Interscience, New York (1974), p. 37 d) P. Murray-Rust and W. D. S. Motherwell, J. Am. Chem. Soc., 101, 4374 (1979).
99. In respect of the CH⋯O, CH⋯Cl, C⋯O, weak interactions, see the following references: a) R. Taylor and O. Kennard, J. Am. Chem. Soc., 104, 5063 (1982) b) G. R. Desiraju, Acc. Chem. Res., 24, 290 (1991) c) T. Bernstein, M. D. Coben, and L. L. Witz, "The Chemistry of Quinonoid Compounds," ed by S. Patai, Interscience, New York (1974), p. 37 d) P. Murray-Rust and W. D. S. Motherwell, J. Am. Chem. Soc., 101, 4374 (1979).
100. In respect of the CH⋯O, CH⋯Cl, C⋯O, weak interactions, see the following references: a) R. Taylor and O. Kennard, J. Am. Chem. Soc., 104, 5063 (1982) b) G. R. Desiraju, Acc. Chem. Res., 24, 290 (1991) c) T. Bernstein, M. D. Coben, and L. L. Witz, "The Chemistry of Quinonoid Compounds," ed by S. Patai, Interscience, New York (1974), p. 37 d) P. Murray-Rust and W. D. S. Motherwell, J. Am. Chem. Soc., 101, 4374 (1979).
101. T. Kurihara, S. Ishikawa, and T. Nozoe, Bull. Chem. Soc. Jpn., 65, 1151 (1992).
102. a) J. Aihara, Bull. Chem. Soc. Jpn., 48, 1501 (1975)
103. b) J. Aihara, J. Am. Chem. Soc., 98, 2750 (1976)
104. c) J. Aihara and T. Horikawa, Bull. Chem. Soc. Jpn., 56, 1853 (1983)
105. d) J. Aihara, J. Am. Chem. Soc., 101, 5913 (1979)
106. e) J. Aihara, Bull. Chem. Soc. Jpn., 51, 3540 (1978).
107. S. Itô and Y. Fujise, "The Thermal Cycloaddition Reaction of Tropylium Compounds," in "Topics in Nonbenzenoid Aromatic Chemistry," ed by T. Nozoe, R. Breslow, K. Hafner, S. Itô, and I. Murata, Hirokawa Publ. Co., Tokyo (1977), Vol. 2, p. 91.
108. a) D. M. Bradby and G. I. Fray, J. Chem. Soc., Perkin Trans. 1, 1972, 195
109. b) H. Takeshita, Y. Wada, A. Mori, and T. Hatsui, Chem. Lett., 1973, 335
110. c) T. Nozoe, T. Mukai, T. Nagase, and Y. Toyooka, Bull. Chem. Soc. Jpn., 33, 1247 (1960)
111. d) R. C. Cookson, B. V. Drake, J. Hudec, and A. Morrison, J. Chem. Soc., Chem. Commun., 1966, 15
112. e) S. Itô, Y. Fujise, T. Okuda, and Y. Inoue, Bull. Chem. Soc. Jpn., 39, 1351 (1966)
113. f) H. Takeshita, H. Nakashima, S. Sugiyama, and A. Mori, Bull. Chem. Soc. Jpn., 61, 573 (1988)
114. g) T. Uyehara, M. Funamizu, and Y. Kitahara, Chem. Ind., 1970, 1500.
115. For the convenience, the term, [m+n], denotes the mode of the reaction between the mπ component of azulenequinone and nπ component of the counterpart.
116. a) H. Takeshita, S. Sugiyama, and T. Hatsui, Chem. Lett., 1984, 1855
117. b) H. Takeshita, S. Sugiyama, and T. Hatsui, J. Chem. Soc., Perkin Trans. 2, 1986, 1491
118. c) W. J. le Noble and B. A. Ojosipe, J. Am. Chem. Soc., 97, 5939 (1975).
119. T. Nozoe, H. Takeshita, Y.-Z. Yan, and A. Mori, Synlett, 1995, 375.
120. H. Takeshita, Y.-Z. Yan, N. Kato, A. Mori, and T. Nozoe, Tetrahedron Lett., 1995, 5199.
121. T. Machiguchi, T. Hasegawa, S. Itô, and H. Mizuno, J. Am. Chem. Soc., 111, 1920 (1989).
122. H. Takeshita, Y.-Z. Yan, A. Mori, and T. Nozoe, Heterocycles, 43, 527 (1996).
123. H. Takeshita, Y.-Z. Yan, N. Kato, A. Mori, and T. Nozoe, Tetrahedron Lett., 1995, 5195.
124. a) T. Mukai, T. Tezuka, and Y. Akasaki, J. Am. Chem. Soc., 88, 5025 (1966)
125. b) A. S. Kende, J. Am. Chem. Soc., 88, 5026 (1966)
126. c) T. Mukai, T. Miyashi, and M. C. Woods, Tetrahedron Lett., 1967, 433
127. d) T. Mukai, T. Tezuka, and Y. Akasaki, Tetrahedron Lett., 1967, 1397.
128. S. Wu, A. Mori, and H. Takeshita, J. Chem. Soc., Chem. Commun., 1994, 919.
129. H. Takeshita, H. Kawakami, N. Kato, A. Mori, and T. Nozoe, Photochem. Photobiol., submitted.
130. W.-C. Wun, T.-C. Huang, S.-J. Lin, B.-B. Lin, T. Morita, and Y.-S. Lin, J. Chin. Chem. Soc., 40, 593 (1993).
131. Y.-C. Lin, W.-C. Wun, T.-C. Huang, T. Morita, and T. Nozoe, Formosan Sci., 47, 107 (1994).
132. K. Takagi, A. Mizuno, T. Joyama, T. Tsuji, H. Wakabayashi, and T. Nozoe, Chem. Express, 1992, 25, although they gave an erroneous structure to compound 281.
133. T. Nozoe, T.-C. Huang, M.-H. Shyr, Y.-S. Lin, and H. Takeshita, Synlett, 1995, 952.
134. Y.-S. Lin, T.-C. Huang, S.-Y. Chiang, C.-H. Dai, and T. Nozoe, to be published.
135. Y. Matsubara, Yuki Gosei Kagaku Kyokai Shi, 50, 963 (1992).
136. C.-C. Lin, T. Nozoe, L.-C. Lin, S.-C. Tsay, P.-W. Yang, and J.-R. Hwu, presented at "the 1995 National Meeting of the Chemical Society," Taiwan, Taichung, Nov. 1995, P2-OR-05, Abstr., p. 220.