A facile synthesis of isoindolo[2,1-a]quinolin-11-one via [4+2] reactions of N-acyliminium intermediates with olefines

Tetrahedron Letters

Volumn 46, Issue 34, 2005, Pages 5691-5694

  Zhang, Wei ^a   Zheng, Airong ^a   Liu, Zhengang ^a   Yang, Li ^a   Liu, Zhongli ^a  

^a LANZHOU UNIVERSITY   (China)

Author keywords

2,3 Dihydro 3 hydroxy 2 arylisoindol 1 one; 5,6,6a,12 Tetrahydroisoindolo 2,1 a quinolin 11 ones; N Acyliminium cation

Indexed keywords

ALKENE DERIVATIVE; BORON DERIVATIVE; CATION; FLUORINE DERIVATIVE; IMINE; INDOLE DERIVATIVE; ISOINDOLO[2,1 A]QUINOLIN 11 ONE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; ENVIRONMENTAL TEMPERATURE; MOLECULE;

EID: 22644432437     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.06.097     Document Type: Article

References (27)

1. Y. Ishihara, Y. Kiyota, and G. Goto Chem. Pharm. Bull. 38 1990 3024 3030
2. Z. Sui, J. Altom, V.N. Nguyen, J. Fernandez, J.I. Bernstein, J.J. Hiliard, J.F. barrett, B.L. Podlogar, and K.A. Ohemeng Bioorg. Med. Chem. 6 1998 735 742
3. J.D. White, and M.E. Mann Adv. Heterocycl. Chem. 10 1969 113 134
4. R. Bonnett, and S.A. North Adv. Heterocycl. Chem. 29 1981 341 399
5. D.B. Reuschling, and F. Krohnke Chem. Ber. 104 1971 2103 2109
6. Y. Abe, A. Ohsawa, and H. Igeta Heterocycles 19 1982 49 51
7. S. Sugasawa, and K. Kodama J. Pharm. Soc. Jpn. 62 1942 367 375
8. H. de Diesbach, G. Rev-Bellet, and T.Sh. Kiang Helv. Chim. Acta 26 1943 1869 1885
9. J. Epsztajn, A. Jozwiak, P. Koluda, I. Sadokierska, and I.D. Wilkowska Tetrahedron 56 2000 4837 4844
10. P. Kumar, C.U. Dinesh, and B. Pandey Tetrahedron Lett. 35 1994 9229 9232
11. A.V. Varlamov, F.I. Zubkov, E.V. Boltukhina, N.V. Sidorenko, and R.S. Borisov Tetrahedron Lett. 44 2003 3641 3643
12. B.E. Maryanoff, H.-C. Zhang, J.H. Cohen, I.J. Turchi, and C.A. Maryanoff Chem. Rev. 104 2004 1431 1628
13. J. Royer, M. Bonin, and L. Micouin Chem. Rev. 104 2004 2311 2351
14. W.N. Speckamp, and H. Hiemstra Tetrahedron 41 1985 4367 4416
15. F. He, Y. Bo, J.D. Altom, and E.J. Corey J. Am. Chem. Soc. 121 1999 6771 6772
16. H. Hiemstra, and W.N. Speckamp Alkaloids 32 1988 271 339
17. H. Hiemstra, and W.N. Speckamp B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 2 1991 Pergamon Oxford 1047 1082
18. D.J. Hart Alkaloids: Chem. Biol. Perspect. 6 1988 227 296
19. P. Pigeon, M. Othman, P. Netchitailo, and B. Decroix J. Heterocycl. Chem. 36 1999 691 695
20. P. Pigeon, and B. Decroix Synth. Commun. 28 1998 2507 2516
21. W. Zhang, Y. Guo, Z. Liu, X. Jin, L. Yang, and Z.L. Liu Tetrahedron 43 2005 9433 9436
22. C. Huo, R. Wei, W. Zhang, L. Yang, J. Lu, and Z.L. Liu Synlett 2005 161 163
23. C. Huo, X. Jia, W. Zhang, L. Yang, J. Lu, and Z.L. Liu Synlett 2004 251 254
24. W. Zhang, X. Jia, L. Yang, and Z.L. Liu Tetrahedron Lett. 43 2002 9433 9436
25. X. Jia, H. Lin, C. Huo, W. Zhang, J. Lu, L. Yang, and Z.L. Liu Synlett 2003 1707 1709
26. W. Zhang, X. Shao, L. Yang, Z.L. Liu, and Y.L. Chow J. Chem. Soc., Perkin Trans. 2 2002 1029 1032
27. 2: C, 78.33; H, 5.88; N, 4.81.