Metalation-cyclisation sequence on N-(o-halobenzyl)pyrroles. Synthesis of pyrrolo[1,2-b]isoquinolones

Tetrahedron Letters

Volumn 41, Issue 27, 2000, Pages 5211-5214

  Ardeo, Ainhoa ^a   Lete, Esther ^a   Sotomayor, Nuria ^a  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Cyclisation; Lithiation; Pyrroles; Pyrroloisoquinolines

Indexed keywords

PYRROLE DERIVATIVE; QUINOLONE DERIVATIVE;

ALKYLATION; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034234821     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00817-0     Document Type: Article

References (26)

1. For a review on aromatic metalation, see: Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon: Exeter, 1995; Vol. 11, p. 2.
2. (a) For a review, see: Parham, W. E.; Bradsher, C. K. Acc. Chem. Res. 1982, 15, 305.
3. (b) For some more recent examples see Ref. 1 and 4.
4. (a) Negishi, N.; Chaneiry, D. In Comprehensive Organic Functional Group Transformations; Katrizky, A. R.; Meth-Cohn, O.; Rees, C. W., Eds.; Pergamon: Cambridge, 1995; Vol. 2, p. 951.
5. (b) Schlosser, M. In Organometallics in Synthesis; Schlosser, M., Ed.; John Wiley & Sons: Chichester, 1995; p. 2.
6. For some representative examples, see: (a) imide carbonyl: Hendi, M. S.; Natalie, K. J.; Hendi, S. B.; Campbell, J. A.; Greenwood, T. D.; Wolfe, J. F. Tetrahedron Lett. 1989, 30, 275.
7. (b) ketone carbonyl: Aidhen, I. S.; Narashimhan, N. S. Tetrahedron Lett. 1991, 32, 2171; Kihara, M.; Kashimoto, M.; Kobayashi, Y. Tetrahedron 1992, 48, 6.
8. (b) ketone carbonyl: Aidhen, I. S.; Narashimhan, N. S. Tetrahedron Lett. 1991, 32, 2171; Kihara, M.; Kashimoto, M.; Kobayashi, Y. Tetrahedron 1992, 48, 6.
9. (c) amide carbonyl: Aidhen, I. S.; Ahuja, J. R. Tetrahedron Lett. 1992, 33, 5431; Quallich, G. J.; Fox, D. E.; Friedmann, R. C.; Murtishaw, C. W. J. Org. Chem. 1992, 57, 761.
10. (c) amide carbonyl: Aidhen, I. S.; Ahuja, J. R. Tetrahedron Lett. 1992, 33, 5431; Quallich, G. J.; Fox, D. E.; Friedmann, R. C.; Murtishaw, C. W. J. Org. Chem. 1992, 57, 761.
11. (d) ester carbonyl: Paleo, M. R.; Castedo, L.; Domínguez, D. J. Org. Chem. 1993, 58, 2763.
12. (e) dithioester carbonyl: Beak, P.; Park, Y. S.; Reif, L. A.; Liu, C. J. Org. Chem. 1994, 59, 7410.
13. (f) imine: Bradsher, C. K.; Hunt, D. A. J. Org. Chem. 1981, 46, 327.
14. (g) alkene: Zhang, D.; Liebeskind, L. S. J. Org. Chem. 1996, 61, 2594.
15. Hoshino, O. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 51, p. 324.
16. Herbert, R. B.; Jackson, F. B.; Nicolson, I. T. J. Chem Soc., Perkin Trans. 1 1984, 825.
17. (a) Collado, M. I.; Sotomayor, N.; Villa, M. J.; Lete, E. Tetrahedron Lett. 1996, 37, 6193.
18. (b) Collado, M. I.; Manteca, I.; Sotomayor, N.; Villa, M. J.; Lete, E. J. Org. Chem. 1997, 62, 2080.
19. Iwao, M.; Mahalanabis, K. K.; Watanabe, M.; de Silva, S. O.; Snieckus, V. Tetrahedron 1983, 39, 1955.
20. Clark, A. J.; Filik, R. P.; Peacock, J. L.; Thomas, G. H. Synlett 1999, 441.
21. Cho, I.-S.; Tu, C.-L.; Mariano, P. S. J. Am. Chem. Soc. 1990, 112, 3594.
22. 3: C, 69.12; H, 5.39; N, 5.76. Found: C, 69.24; H, 5.41; N, 5.84.
23. Bromides 1 and 2 were prepared from benzylic alcohols. All aromatic iodination reactions were completely regioselective, except case f, which afforded a 2:1 mixture of 6-iodo and 5-iodo alcohols, resulting in a low yield of the desired 3f, after separation of isomers.
24. In all cases, variable amounts (7-13%) of the corresponding deiodinated benzylpyrroles were isolated together with pyrrolisoquinolones 5.
25. (a) Beak, P.; Allen, D. J. J. Am. Chem. Soc. 1992, 114, 3420.
26. (b) Reich, J. H.; Green, D. P.; Phillips, N. H. J. Am. Chem. Soc. 1991, 113, 1414.