Efficient synthesis of 9H-pyrrolo[1,2-a]indol-9-one derivatives based on active manganese dioxide promoted intramolecular cyclization

Tetrahedron

Volumn 66, Issue 1, 2010, Pages 274-277

  Aiello, Francesca ^a   Garofalo, Antonio ^a   Grande, Fedora ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

2 (1H Pyrrol 1 yl)benzaldehyde; 9H Pyrrolo 1,2 a indol 9 one; Intramolecular cyclization; Oxidation

Indexed keywords

5 METHOXY 2 (1H PYRROL 1 YL)BENZALDEHYDE; 5 METHYL 9H PYRROLO(1,2 A)INDOL 9 ONE; 7 FLUORO 9H PYRROLO(1,2 A)INDOL 9 ONE; 7 METHOXY 9H PYRROLO(1,2 A)INDOL 9 ONE; 7 METHYL 9H PYRROLO(1,2 A)INDOL 9 ONE; 7 NITRO 9H PYRROLO(1,2 A)INDOL 9 ONE; 9H PYRROLO(1,2-A)INDOL 9 ONE; [2 (1H PYRROL 1 YL)PHENYL]METHANOL; [3 METHYL 2 (1H PYRROL 1 YL)PHENYL]METHANOL; [5 FLUORO 2 (1H PYRROL 1 YL)PHENYL]METHANOL; [5 METHOXY 2 (1H PYRROL 1 YL)PHENYL]METHANOL; [5 METHYL 2 (1H PYRROL 1 YL)PHENYL]METHANOL; [5 NITRO 2 (1H PYRROL 1 YL)PHENYL]METHANOL; INDOLE DERIVATIVE; MANGANESE DIOXIDE; METHANOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; DRUG DETERMINATION; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL;

EID: 70549105969     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.10.111     Document Type: Article

References (26)

1. Fogassy K., Kovács K., Keseru{combining double acute accent} G.M., To{combining double acute accent}ke L., and Faigl F. J. Chem. Soc., Perkin Trans. 1 (2001) 1039
2. Artico M., Giuliano R., Porretta G.C., and Scalzo M. Il Farmaco 27 (1972) 60
3. Porretta G.C., Filacchioni G., Stefancich G., Giuliano R., and Artico M. Il Farmaco 33 (1978) 263
4. Rault S., Lancelot J.C., Bouyazza L., Robba M., Quermonne M.A., Nammathao B., Louchahi-Raoul J., and Marcy R. Eur. J. Med. Chem. 26 (1991) 939
5. Lisowsky V., Léonce S., Kraus-Berthier L., Sopkovà-de Oliveira Santos J., Pierré A., Atassi G., Caignard D.H., Renard P., and Rault S. J. Med. Chem. 47 (2004) 1448
6. Bauer R., Heisler G., and Konigstein C. Spectrochim. Acta, Part A 50A (1994) 57
7. Grande G., Yamada R., Cao X., Aiello F., Garofalo A., and Neamati N. Expert Opin. Investig. Drugs 18 (2009) 555
8. Josey A.D., and Jenner E.L. J. Org. Chem. 27 (1962) 2466
9. Mazzola V.J., Bernady K.F., and Franck R.W. J. Org. Chem. 32 (1967) 486
10. Bailey A.S., Scott P.W., and Vandrevala M.H. J. Chem. Soc., Perkin Trans. 1 (1980) 97
11. Campo M.A., and Larock R.C. J. Org. Chem. 67 (2002) 5616
12. Kashulin I.A., and Nifant'ev I.E. J. Org. Chem. 69 (2004) 5476
13. Kobayashi K., Himei Y., Fukamachi S., Tanmatsu M., Morikawa O., and Konishi H. Tetrahedron 63 (2007) 4356
14. Garofalo A., Ragno G., Campiani G., Brizzi A., and Nacci V. Tetrahedron 56 (2000) 9351
15. Basha F.Z., and Franck R.W. J. Org. Chem. 43 (1978) 3415
16. Tojo G., and Fernandez M. Oxidation of Alcohols to Aldehydes and Ketones (2006), Springer, New York, NY 290-309
17. Pratt E.F., and Van De Castle J.F. J. Org. Chem. 26 (1961) 2973
18. Wei X., and Taylor R.J.K. Tetrahedron Lett. 39 (1998) 3815
19. Maki B.E., Chan A., Phillips E.M., and Scheidt K.A. Org. Lett. 9 (2007) 371
20. Taylor R.J.K., Reid M., Foot M.J., and Raw S.A. Acc. Chem. Res. 38 (2005) 851
21. Pratt E.F., and McGovern T.P. J. Org. Chem. 29 (1964) 1540
22. Barton T.J., and Banasiak D.S. J. Organomet. Chem. 157 (1978) 255
23. Malakov P.Y., De la Torre M.C., Rodriguez B., and Papanov G. Tetrahedron 47 (1991) 10129
24. Attenburrow J., Cameron A.F.B., Chapman J.H., Evans R.M., Hems B.A., Jansen A.B.A., and Walker T. J. Chem. Soc. (1952) 1094
25. Bavetsias V., Skelton L.A., Yafai F., Mitchell F., Wilson S.C., Allan B., and Jackman A.L. J. Med. Chem. 45 (2002) 3692
26. Paillet-Loilier M., Fabis F., Lepailleur A., Bureau R., Butt-Gueulle S., Dauphin F., Delarue C., Vaudry H., and Rault S. Bioorg. Med. Chem. Lett. 15 (2005) 3753