Synthesis of 5,6-dihydropyrrolo[2,1-a]isoquinolines by rearrangement of 5-methyleneisoxazolidines generated from 1,3-dipolar cycloaddition of 3,4-dihydroisoquinoline N-oxides with allenes: A novel consecutive rearrangement to fused-ring pyrrole derivatives

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1997, Pages 2973-2977

  Zhao, Bao Xiang ^a   Eguchi, Shoji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748674235     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a704066k     Document Type: Article

References (21)

1. (a) W. K. Anderson, A. R. Heider, N. Raju and J. A. Yucht, J. Med. Chem., 1988, 31, 2097;
2. (b) W. K. Anderson, H. L. McPherson, Jr., J. S. New and A. C. Rick, J. Med. Chem., 1984, 27, 1321.
3. (a) Y. Ban and M. Terashima, Tetrahedron Lett.. 1961, 22, 796;
4. (b) Y. Ban and M. Terashima, Chem. Pharm. Bull., 1965, 13, 775;
5. (c) S.-I. Sakai, A. Kubo, M. Inaba, M. Katagiri and K. Tanno, Yakugaku Zasshi, 1966, 86, 856;
6. (d) C. Casagrande, A. Invernizzi, R. Ferrini and G. G. Ferrari, J. Med. Chem., 1968, 11, 765.
7. (a) R. Grigg, J. Montgomery and A. Somasunderam, Tetrahedron, 1992, 48, 10431;
8. (b) R. Grigg, P. Kennewell, V. Savic and V. Sridharan, Tetrahedron, 1992, 48, 10423;
9. (c) R. Grigg, P. Myers, A. Somasunderam and V. Sridharan, Tetrahedron, 1992, 48, 9735;
10. (d) R. Grigg, H. Q. N. Gunaratne, D. Henderson and V. Sridharan, Tetrahedron, 1990, 46, 1599.
11. Y. Tominaga, Y. Shiroshita, T. Kurokawa, H. Gotou, Y. Matsuda and A. Hosomi, J. Heterocycl. Chem., 1989, 26, 477.
12. H. H. Wasserman, R. Frechette, T. Oida and J. H. van Duzer, J. Org. Chem., 1989, 54, 6012.
13. W. Lösel, Chem. Ber., 1988, 121, 547.
14. B.-X. Zhao, Y. Yu and S. Eguchi, Tetrahedron, 1996, 52, 12 049.
15. M. S. Algharib, J. Chem. Res., 1996, (S), 384.
16. P. Nemes, M. Kajtár-Peredy and P. Scheiber, Synlett, 1996, 623.
17. B.-X. Zhao and S. Eguchi, Tetrahedron, 1997, 53, 9575.
18. I. Bata, D. Korbonits, G. Héja, P. Kolonits and K. Simon, ACH-Models Chem., 1994, 131 (3-4), 351.
19. S. Eguchi, K. Asai and T. Sasaki, Heterocycles, 1989, 28, 125.
20. J. E. Baldwin, R. G. Pudussery, A. K. Qureshi and B. B. Sklarz, J. Am. Chem. Soc., 1968, 90, 5325.
21. B.-X. Zhao, Y. Yu and S. Eguchi, Org. Prep. Proced. Int., 1997, 29 (2), 185.