Regioselective oxidation of pyrrole derivatives with DDQ and its synthetic application

Chemistry Letters

Volumn 39, Issue 3, 2010, Pages 176-177

  Iwamoto, Ryoji ^a   Ukaji, Yutaka ^a   Inomata, Katsuhiko ^a  

^a KANAZAWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 77249114712     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2010.176     Document Type: Article

References (22)

1. K. Inomata, Bull. Chem. Soc. Jpn. 2008, 81, 25, and references cited therein.
2. M. A. S. Hammam, Y. Murata, H. Kinoshita, K. Inomata, Chem. Lett. 2004, 33, 1258;
3. H. Kinoshita, M. A. S. Hammam, K. Inomata, Chem. Lett. 2005, 34, 800;
4. K. Inomata, M. A. S. Hammam, H. Kinoshita, Y. Murata, H. Khawn, S. Noack, N. Michael, T. Lamparter, J. Biol. Chem. 2005, 280, 24491;
5. M. A. S. Hammam, H. Nakamura, Y. Hirata, H. Khawn, Y. Murata, H. Kinoshita, K. Inomata, Bull. Chem. Soc. Jpn. 2006, 79, 1561;
6. K. Inomata, S. Noack, M. A. S. Hammam, H. Khawn, H. Kinoshita, Y. Murata, N. Michael, P. Scheerer, N. Krauß, T. Lamparter, J. Biol. Chem. 2006, 281, 28162;
7. H. Khawn, L.-Y. Chen, H. Kinoshita, K. Inomata, Chem. Lett. 2008, 37, 198;
8. K. Inomata, H. Khawn, L.-Y. Chen, H. Kinoshita, B. Zienicke, I. Molina, T. Lamparter, Biochemistry 2009, 48, 2817;
9. L.-Y. Chen, H. Kinoshita, K. Inomata, Chem. Lett. 2009, 38, 602.
10. D. Walker, J. D. Hiebert, Chem. Rev. 1967, 67, 153;
11. A. B. Turner, in Synthetic Reagents, ed. by J. S. Pizey, Halstead-Wiley, New York, 1977, Vol. 3, p. 193.
12. T. Ishiguro, H. Mizuguchi, K. Tomioka, K. Koga, Chem. Pharm. Bull. 1985, 33, 609.
13. 3-pyrromethenones with DDQ occurred at 5′-position to generate the corresponding azafulvene intermediate: H. Falk, K. Grubmayr, Synthesis 1977, 614;
14. H. Falk, T. Schlederer, Monatsh. Chem. 1981, 112, 501.
15. 2 for 5 d in the presence of MeOH (10 equiv) and 1a was recovered.
16. Regiochemistry of the products 2c, 2d, 6c, and 6d was confirmed by NOE measurement. The NOEs between H at the C-5 position and α- or β-H of the substituent at the C-4 position were observed.
17. H. Kinoshita, H. Ngwe, K. Kobori, K. Inomata, Chem. Lett. 1993, 1441;
18. K. Kohori, M. Hashimoto, H. Kinoshita, K. Inomata, Bull. Chem. Soc. Jpn. 1994, 67, 3088.
19. Previous examples of the preparation of 4-formyl-1H-pyrrole-2- carboxylates through the Barton reaction using acetoxy nitro compounds possessing an acetal moiety or the Vilsmeier reaction: Y. Fumoto, H. Uno, S. Ito, Y. Tsugumi, M. Sasaki, Y. Kitawaki, N. Ono, J. Chem. Soc., Perkin Trans. 1, 2000, 2977;
20. T. D. Lash, T. H. Nguyen, Z. Hu, Synlett 1994, 905;
21. Furthermore, 4-(1-acetoxyalkyl)-1H-pyrrole-2-carboxylates were synthesized by the reduction of the corresponding carbonyl compounds followed by acetylation: T. D. Lash, K. A. Bladel, C. M. Shiner, D. L. Zajeski, R. P. Balasubramaniam, J. Org. Chem. 1992, 57, 4809;
22. R. Ahmed, F. J. Leeper, Org. Biomol. Chem. 2003, 1, 21.