Abstract
It is a characteristic of all spirobenzylisoquinolines known,1 including those recently reported and indicated below, to possess a methylenedioxy group in the bottom ring.
Keywords
Isoquinoline Alkaloid Sodium Cyanoborohydride Diethyl Acetal Pyridinium Bromide Methylenedioxy Group
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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References
- 1.For a review on the spirobenzylisoquinolines, see S. McLean and J. Whelan, MTP Int. Rev. of Sci., Alkaloids, Org. Chem., Series One, K. Wiesner, ed., Vol. 9, Butterworths, London (1973), p. 161.Google Scholar
- 2.S.-T. Lu, T.-L. Su, T. Kametani, and M. Ihara, Heterocycles, 3, 301 (1975); andCrossRefGoogle Scholar
- 2a.S.-T. Lu, T.-L. Su, T. Kametani, A. Ujiie, M. Ihara, and K. Fukumoto, J. Chem. Soc. Perkin I, 63 (1976).CrossRefGoogle Scholar
- 3.T. Kametani, M. Takemura, M. Jhara, and K. Fukumoto, Heterocycles, 4, 723 (1976); andCrossRefGoogle Scholar
- 3a.T. Kametani, M. Takemura, M. Jhara, and K. Fukumoto, J. Chem. Soc. Perkin I, 390 (1977).CrossRefGoogle Scholar
- 4.S. McLean and J. Whelan, Can. J. Chem., 51, 2457 (1973).CrossRefGoogle Scholar
- 5.S. McLean and D. Dime, Can. J. Chem., 55, 924 (1977).CrossRefGoogle Scholar
- 6.H. Irie, A. Kitagawa, A. Kuno, J. Tanaka, and N. Yokotani, Heterocycles, 4, 1083 (1976).CrossRefGoogle Scholar
- 7.N. E. Cundasawmy and D. B. MacLean, Can. J. Chem., 50, 3028 (1972).CrossRefGoogle Scholar
- 8.S. O. de Silva, K. Orito, R. H. Manske, and R. Rodrigo, Tetrahedron Lett., 3243 (1974).Google Scholar
- 9.M. Shamma and J. F. Nugent, Tetrahedron, 29, 1265 (1973).CrossRefGoogle Scholar
- 10.T. Kametani, T. Takahashi, and K. Ogasawara, J. Chem. Soc. Perkin I, 1464 (1973).CrossRefGoogle Scholar
- 10a.For an improved procedure, see T. Kametani, Y. Hirai, H. Nemoto, and K. Fukumoto, J. Heterocycl. Chem., 12, 185 (1975).CrossRefGoogle Scholar
- 11.T. Kametani, H. Takeda, Y. Hirai, F. Satoh, and K. Fukumoto, J. Chem. Soc. Perkin I, 2141 (1974).CrossRefGoogle Scholar
- 12.B. Nalliah, R. H. F. Manske, R. Rodrigo, and D. B. MacLean, Tetrahedron Lett., 2795 (1973).Google Scholar
- 12a.M. Hanaoka and C. Mukai, Heterocycles, 6, 1981 (1977).Google Scholar
- 13.H. L. Holland, D. B. MacLean, R. G. A. Rodrigo, and R. H. F. Manske, Tetrahedron Lett., 4323 (1975).Google Scholar
- 14.B. C. Nalliah, D. B. MacLean, R. G. A. Rodrigo, and R. H. F. Manske, Can. J. Chem., in press.Google Scholar
- 14a. H. L. Holland, M. Curcumelli-Rodostamo, and D. B. MacLean, Can. J. Chem., 54, 1472 (1976).CrossRefGoogle Scholar
- 15.J. Imai, Y. Kondo, and T. Takemoto, Heterocycles, 3, 467 (1975); andCrossRefGoogle Scholar
- 15a.J. Imai, Y. Kondo, and T. Takemoto, Tetrahedron, 32, 1973 (1976).CrossRefGoogle Scholar
- 16.S. Kano, T. Yokomatsu, E. Komiyama, S. Tokita, Y. Takahagi, and S. Shibuya, Chem. Pharm. Bull., Tokyo, 23, 1171 (1975).CrossRefGoogle Scholar
- 17.T. Kametani, S.-P. Huang, A. Ujiie, M. Ihara, and K. Fukumoto, Heterocycles, 4, 1223 (1976); andCrossRefGoogle Scholar
- 17a.T. Kametani, A. Ujiie, S.-P. Huang, M. Ihara, and K. Fukumoto, J. Chem. Soc. Perkin I, 394 (1977).CrossRefGoogle Scholar
- 18.T. Kametani, S. Hirata, S. Hibino, H. Nemoto, M. Ihara, and K. Fukumoto, Heterocycles, 3, 151 (1975); andCrossRefGoogle Scholar
- 18a.T. Kametani, S. Hirata, H. Nemoto, M. Ihara, S. Hibino, and K. Fukumoto, J. Chem. Soc. Perkin I, 2028 (1975).CrossRefGoogle Scholar
- 18b.For the pyrolytic rearrangement of spirobenzylisoquinoline esters to dibenzocyclopentazepines, see N. M. Mollov and G. I. Yakimov, Dokl. Bolg. Akad. Nauk, 24, 1325 (1971).Google Scholar
- 19.H. L. Holland, M. Castillo, D. B. MacLean, and I. D. Spenser, Can. J. Chem., 52, 2818 (1974).CrossRefGoogle Scholar
- 20.A. Kato, K. Akagi, H. Irie, and S. Uyeo, J. Pharm. Soc. Japan, 95, 1058 (1975).Google Scholar
- 21.T. Kametani, S. Hibino, S. Shibuya, and S. Takano, J. Heterocycl. Chem., 9, 47 (1972).CrossRefGoogle Scholar
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© Plenum Press, New York 1978