Rearrangements of cyclobutenones. Synthesis of N-methyl-7,8- dihydrobenzophenanthridine-9,12-diols and related compounds

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5979-5983

  Hergueta, Antonio R ^a   Moore, Harold W ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOBUTANONE DERIVATIVE; PHENANTHRIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CONFORMATIONAL TRANSITION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0033529887     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990505b     Document Type: Article

References (23)

1. For a recent review on the ring expansion of cyclobutenones see: Moore, H. W.; Yerxa B. R. Adv. Strain Org. Chem. 1995, 4, 81.
2. Xiong, Y.; Moore, H. W. J. Org. Chem. 1996, 61, 1, 9168.
3. For an efficient synthesis of dialkyl squarates see: Liu, H.; Tomooka, C. S.; Moore, H. W. Synth. Commun. 1997, 27, 2177.
4. (a) Dostal, J.; Slavik, J.; Potacek, M.; Marek, R.; Humpa, O.; Sklenar, V.; Tousek, J.; de Hoffmann, E.; Rozenberg, R. Collect. Czech. Chem. Commun. 1998, 63, 1045.
5. (b) Krane, B. D.; Fagbule, M. O.; Shamma, M. J. Nat. Prod. 1984, 47, 1.
6. Similar nonplanar structures have been reported for other dihydrophenanthridines. See, for example: (a) Chen, Y.; Tang, G.; Xu, B.; Wu, Q.; Lu, C.; Li, J.; Huang, Z. Sci. China, Ser. B 1992, 35, 1101. (b) Chen, Y.; Xu, B.; Yang, L.; Huang, Z. Chin. Sci. Bull. 1989, 34, 1182. (c) Chen, Y.; Yang, L.; Xu, B. Acta Chim. Sin. 1989, 47, 1048.
7. Similar nonplanar structures have been reported for other dihydrophenanthridines. See, for example: (a) Chen, Y.; Tang, G.; Xu, B.; Wu, Q.; Lu, C.; Li, J.; Huang, Z. Sci. China, Ser. B 1992, 35, 1101. (b) Chen, Y.; Xu, B.; Yang, L.; Huang, Z. Chin. Sci. Bull. 1989, 34, 1182. (c) Chen, Y.; Yang, L.; Xu, B. Acta Chim. Sin. 1989, 47, 1048.
8. Similar nonplanar structures have been reported for other dihydrophenanthridines. See, for example: (a) Chen, Y.; Tang, G.; Xu, B.; Wu, Q.; Lu, C.; Li, J.; Huang, Z. Sci. China, Ser. B 1992, 35, 1101. (b) Chen, Y.; Xu, B.; Yang, L.; Huang, Z. Chin. Sci. Bull. 1989, 34, 1182. (c) Chen, Y.; Yang, L.; Xu, B. Acta Chim. Sin. 1989, 47, 1048.
9. Niwayama, S.; Kallel, E. A.; Sheu, C. M.; Houk, K. N.; J. Org. Chem. 1996, 61, 2517.
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11. For a review of radical arylations, see: Waters, W. A. Free Radicals Reactions; Butterworth: London, 1987; Chapter 3, pp 25-45.
12. Xiong, Y.; Xia, H.; Moore, H. W. J. Org. Chem. 1995, 60, 6460.
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15. Nakanishi, T.; Suzuki, M.; Mashiba, A.; Ishikawa, K.; Yokotsuka, T. J. Org. Chem. 1998, 63, 4235.
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18. Gobert, F.; Combrisson, S. Tetrahedron 1974, 30, 2919.
19. The synthesis of this compound differs slightly from that reported by: (a) Begley, W. J.; Grimshaw, J. J. Chem. Soc., Perkin Trans. I 1977, 2324. (b) Kessar, S. V.; Gupta, Y. P.; Balakrishnan, P.; Sawal, K. K.; Mohammad, T.; Dutt, M. J. Org. Chem. 1988, 53, 1708.
20. The synthesis of this compound differs slightly from that reported by: (a) Begley, W. J.; Grimshaw, J. J. Chem. Soc., Perkin Trans. I 1977, 2324. (b) Kessar, S. V.; Gupta, Y. P.; Balakrishnan, P.; Sawal, K. K.; Mohammad, T.; Dutt, M. J. Org. Chem. 1988, 53, 1708.
21. The procedure used is similar to that described for the synthesis of N-methyl-1-naphthylamine from 1-naphthylamine: (a) Katritzky, A. R.; Black, M.; Fan, W. J. Org. Chem. 1991, 56, 6, 5045. (b) Katritzky, A. R.; Rachwall, S.; Rachwal, B. J. Chem. Soc., Perkin Trans. 1 1987, 805.
22. The procedure used is similar to that described for the synthesis of N-methyl-1-naphthylamine from 1-naphthylamine: (a) Katritzky, A. R.; Black, M.; Fan, W. J. Org. Chem. 1991, 56, 6, 5045. (b) Katritzky, A. R.; Rachwall, S.; Rachwal, B. J. Chem. Soc., Perkin Trans. 1 1987, 805.
23. DDQ has been employed to accomplish this reaction in related systems. See, for example: Hanaoka, M.; Kobayashi, K.; Shimada, K.; Mukai, C. J. Chem. Soc., Perkin Trans. 1 1987, 677.