Synthesis of 2-allyl-2,3-dihydro-1H-indol-3-ones using in situ Claisen rearrangement of 2,3-dihydro-1H-indol-3-ones with allyl alcohols

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 7, 1996, Pages 729-733

  Kawasaki, Tomomi ^a   Masuda, Kouhei ^a   Baba, Yasutaka ^a   Terashima, Romi ^a   Takada, Kana ^a   Sakamoto, Masanori ^a  

^a MEIJI PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001504251     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960000729     Document Type: Article

References (28)

1. J. Y. Merour, J. Y. Coadou and F. Tatibouet, Synthesis, 1982, 1053;
2. A. Buzas, C. Herisson and G. Lavielle, Synthesis, 1977, 129;
3. K. N. Kilminster and M. Sainsbury, J. Chem. Soc., Perkin Trans. 1, 1972, 2264;
4. F. Nivoliers, A. Decormeille, A. Godard and G. Quequiner, Tetrahedron Lett., 1980, 21, 4485;
5. G. Argiropoulos, L. W. Deady and M. Dorkos, Aust. J. Chem., 1991, 44, 481;
6. T. Kawasaki, Y. Nonaka, M. Uemura and M. Sakamoto, Synthesis, 1991, 701;
7. T. Kawasaki, Y. Nonaka, M. Akahane, N. Maeda and M. Sakamoto, J. Chem. Soc., Perkin Trans. 1, 1993, 1777.
8. P. S. Steyn, Tetrahedron Lett., 1971, 3331.
9. A. J. Birch and J. J. Wright, J. Chem. Soc., Chem. Commun., 1969, 644;
10. A. J. Birch and R. A. Russell, Tetrahedron, 1972, 28, 2999.
11. M. Barbetta, G. Casnati, A. Pochini and A. Silva, Tetrahedron Lett., 1969, 4457.
12. T. A. Smitka, R. Bonjouklian, L. Doolin, N. D. Jones, J. B. Deeter, W. Y. Yoshida, M. R. Prinsep, R. E. Moore and G. M. L. Patterson, J. Org. Chem., 1992, 57, 857;
13. C. Christopherson, The Alkaloids, 1985, 24, 25;
14. M. A. O'Leary and J. R. Hanson, Tetrahedron Lett., 1982, 23, 1855.
15. J. F. Sanz-Cervera, T. Glinka and R. M. Williams, J. Am. Chem. Soc., 1993, 115, 347.
16. (a) J.-Y. Mérour, L. Chichereau and J.-P. Finet, Tetrahedron Lett., 1992, 33, 3867;
17. (b) T. Kawasaki, Y. Nonaka, M. Kobayashi and M. Sakamoto, J. Chem. Soc., Perkin Trans. 1, 1991, 2445 and references cited therein;
18. S. C. Conway and G. W. Gribble, Heterocycles, 1990, 30, 627;
19. A. Buzas and J.-Y. Mérour, Synthesis, 1989, 458;
20. (e) H. Plieninger, H. Sirowej and D. Rau, Chem. Ber., 1971, 104, 1863;
21. (f) E. Houghton and J. E. Saxton, J. Chem. Soc. (C), 1969, 595.
22. T. Kawasaki, K. Masuda, Y. Baba, K. Takada and M. Sakamoto, Chem. Pharm. Bull., 1994, 42, 1974.
23. C.-S. Chien, A. Hasegawa, T. Kawasaki and M. Sakamoto, Chem. Pharm. Bull., 1986, 34, 1493.
24. P. Wipf, in Comprehensive Organic Synthesis, ed. B. M. Trost, Pergamon, Oxford, 1991, p. 827;
25. F. E. Zieglar, Chem. Rev., 1988, 88, 1423;
26. S. J. Rhoads and N. R. Raulins, Org. React. (N. Y.), 1975, 22, 1.
27. C.-S. Chien, T. Suzuki, T. Kawasaki and M. Sakamoto, Chem. Pharm. Bull., 1984, 32, 3945.
28. T. Kawasaki, H. Ohtsuka, C.-S. Chien, M. Omata and M. Sakamoto, Chem. Pharm. Bull., 1987, 35, 1339.