Carboxylation of indoles and pyrroles with CO2 in the presence of dialkylaluminum halides

Tetrahedron Letters

Volumn 50, Issue 31, 2009, Pages 4512-4514

  Nemoto, Koji ^a   Onozawa, Satoru ^a   Egusa, Naoki ^a   Morohashi, Naoya ^a   Hattori, Tetsutaro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alumination; Carboxylation; Indolecarboxylic acid; Pyrrolecarboxylic acid

Indexed keywords

2 PYRROLECARBOXYLIC ACID; 3 INDOLECARBOXYLIC ACID; ALUMINUM DERIVATIVE; CARBON DIOXIDE; CARBOXYLIC ACID DERIVATIVE; HALIDE; INDOLE DERIVATIVE; LEWIS ACID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOXYLATION; DRUG SYNTHESIS; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 66949138593     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.076     Document Type: Article

References (32)

1. Boriskin Y.S., Leneva I.A., Pécheur E.-I., and Polyak S.J. Curr. Med. Chem. 15 (2008) 997
2. Yang Z., Ney A., Cromer B.A., Ng H.-L., Parker M.W., and Lynch J.W. J. Neurochem. 100 (2007) 758
3. Rogers E.F., Koniuszy F.R., Shavel Jr. J., and Folkers K. J. Am. Chem. Soc. 70 (1948) 3086
4. Hagiwara K., Himuro M., Hirama M., and Inoue M. Tetrahedron Lett. 50 (2009) 1035
5. Fisher E., and Jourdan F. Ber. 16 (1883) 2241
6. Ito Y., Kobayashi K., and Saegusa T. J. Am. Chem. Soc. 99 (1977) 3532
7. Hantzsch A. Ber. 23 (1890) 1474
8. Knorr L. Ber. 17 (1884) 1635
9. Park C.M., Kim S.Y., Park W.K., Park N.S., and Seong C.M. Bioorg. Med. Chem. Lett. 18 (2008) 3844
10. Fukuda T., Mine Y., and Iwao M. Tetrahedron 57 (2001) 975 and references cited therein
11. 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 and references cited therein
12. Jones G., and Stanforth S.P. Org. React. 49 (1997) 1
13. Friedel C., and Crafts J.M. Compt. Rend. 86 (1878) 1368
14. Olah G.A., Török B., Joschek J.P., Bucsi I., Esteves P.M., Rasul G., and Prakash G.K.S. J. Am. Chem. Soc. 124 (2002) 11379 and references cited therein
15. Munshi P., and Beckman E.J. Ind. Eng. Chem. Res. 48 (2009) 1059
16. Suzuki Y., Hattori T., Okuzawa T., and Miyano S. Chem. Lett. (2002) 102
17. Hattori T., Suzuki Y., and Miyano S. Chem. Lett. 32 (2003) 454
18. Nemoto K., Yoshida H., Suzuki Y., Morohashi N., and Hattori T. Chem. Lett. 35 (2006) 820
19. 1H NMR analysis of the residue left by the evaporation of the chloroform extract.
20. Baiocchi L., and Giannangeli M. J. Heterocycl. Chem. 25 (1988) 1905
21. Konishi K., Aida T., and Inoue S. J. Org. Chem. 55 (1990) 816
22. Okauchi T., Itonaga M., Minami T., Owa T., Kitoh K., and Yoshino H. Org. Lett. 2 (2000) 1485
23. Huffman J.W., Szklennik P.V., Almond A., Bushell K., Selley D.E., He H., Cassidy M.P., Wiley J.L., and Martin B.R. Bioorg. Med. Chem. Lett. 15 (2005) 4110
24. Huffman J.W., Smith V.J., and Padgett L.W. Tetrahedron 64 (2008) 2104
25. Mingoia Q. Gazz. Chim. Ital. 60 (1930) 509
26. Boev V.I., Denisov S.P., Moskalenko A.I., Stamova L.G., and Gulin A.V. Russ. J. Gen. Chem. 70 (2000) 1812
27. Conway B., Hevia E., Kennedy A.R., and Mulvey R.E. Chem. Commun. (2007) 2864
28. Seggio A., Lannou M.-I., Chevallier F., Nobuto D., Uchiyama M., Golhen S., Roisnel T., and Mongin F. Chem. Eur. J. 13 (2007) 9982
29. Wunderlich S.H., and Knochel P. Angew. Chem., Int. Ed. 46 (2007) 7685
30. Naka H., Uchiyama M., Matsumoto Y., Wheatley A.E.H., McPartlin M., Morey J.V., and Kondo Y. J. Am. Chem. Soc. 129 (2007) 1921
31. Usui S., Hashimoto Y., Morey J.M., Wheatley A.E.H., and Uchiyama M. J. Am. Chem. Soc. 129 (2007) 15102
32. L'Helgoual'ch J.-M., Bentabed-Ababsa G., Chevallier F., Yonehara M., Uchiyama M., Derdour A., and Mongin F. Chem. Commun. (2008) 5375