Acylation of N-p-toluenesulfonylpyrrole under Friedel-Crafts conditions: evidence for organoaluminum intermediates

Tetrahedron

Volumn 64, Issue 9, 2008, Pages 2104-2112

  Huffman, John W ^a   Smith, Valerie J ^a   Padgett, Lea W ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

Acylpyrrole; Friedel Crafts reaction; Organoaluminum intermediates; Reaction mechanism

Indexed keywords

2 (1 NAPHTHOYL) N (4 TOLUENESULFONYL)PYRROLE; 2 PHENYL 4 (1 NAPHTHOYL) N 4 TOLUENESULFONYLPYRROLE; 3 (1 NAPHTHOYL) N (4 TOLUENESULFONYL)PYRROLE; 3 ACETYL N 4 TOLUENESULFONYLPYRROLE; 3 BENZOYL N 4 TOLUENESULFONYLPYRROLE; ACID HALIDE; ALUMINUM CHLORIDE; ALUMINUM DERIVATIVE; LEWIS ACID; N 4 TOLUENESULFONYLPYRROLE; PYRROLE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; FRIEDEL CRAFTS REACTION; PRIORITY JOURNAL;

EID: 38349168986     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.12.043     Document Type: Article

References (43)

1. Anderson H.J., and Loader C.E. Synthesis (1985) 353
2. Muchowski J., and Solas D.R. Tetrahedron Lett. 24 (1983) 3455
3. Bray B.L., Mathies P.H., Naef R., Solas D.R., Tidwell T.T., Artis D.R., and Muchowski J. J. Org. Chem. 55 (1990) 6317
4. Xu R.X., Anderson N.J., Gogan N.J., Loader C.E., and McDonald R. Tetrahedron Lett. 22 (1981) 4899
5. Anderson H.J., Loader C.E., Xu R.X., Le N., Gogan N.J., McDonald R., and Edwards L.G. Can. J. Chem. 63 (1985) 896
6. Rokach J., Hamel P., Kakushima M., and Smith G.M. Tetrahedron Lett. 22 (1981) 4901
7. Kakushima M., Hamel P., Frenette R., and Rokach J. J. Org. Chem. 48 (1983) 3214
8. Lainton J.A.H., Huffman J.W., Martin B.R., and Compton D.R. Tetrahedron Lett. 36 (1995) 1401
9. Reggio P.H., Basu-Dutt S., Barnett-Norris J., Castro M.T., Hurst D.P., Seltzman H.H., Roche M.J., Gilliam A.F., Thomas B.F., Stevenson L.A., Pertwee R.G., and Abood M.E. J. Med. Chem. 41 (1998) 5177
10. Huffman J.W., Mabon R., Wu M.-J., Lu J., Hart R., Hurst D.P., Reggio P.H., Wiley J.L., and Martin B.R. Bioorg. Med. Chem. 11 (2003) 539
11. Huffman J.W., Padgett L.W., Wiley J.L., and Martin B.R. Bioorg. Med. Chem. Lett. 16 (2006) 5432
12. Okauchi T., Itonaga M., Minami T., Owa T., Kitoh K., and Yoshino H. Org. Lett. 2 (2000) 1485
13. Ottoni O., Neder A.V.F., Dias A.K.B., Cruz R.P.A., and Aquino L.B. Org. Lett. 3 (2001) 1005 independently and simultaneously developed a similar procedure for preparing 3-acylindoles
14. Huffman J.W., Zengin G., Wu M.-J., Lu J., Hynd G., Bushell K., Thompson A., Bushell S., Tartal C., Hurst D.P., Reggio P.H., Selley D.E., Cassidy M.P., Wiley J.L., and Martin B.R. Bioorg. Med. Chem. 13 (2005) 89
15. 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
16. Anderson H.J., and Griffiths S.J. Can. J. Chem. 45 (1967) 2227
17. 5, R=Ts).
18. Lainton, J. A. H.; Huffman, J. W. Unpublished work.
19. Sattambolo R., Lazzaroni R., Messeri T., and Salvadori P. J. Org. Chem. 58 (1993) 7899
20. Baddeley G., and Voss D. J. Chem. Soc. (1954) 418
21. Carmona O., Greenhouse R., Landeros R., and Muchowski J.M. J. Org. Chem. 45 (1980) 5336
22. DeSales J., Greenhouse R., and Muchowski J.M. J. Org. Chem. 47 (1982) 3668
23. Carson J.R., and Davis N.M. J. Org. Chem. 46 (1981) 839
24. Arisawa M., Torisawa Y., and Nakagawa M. Synthesis (1995) 1371
25. Arisawa M., Torisawa Y., Kawahara M., Yamanaka M., Nishida A., and Nakagawa M. J. Org. Chem. 62 (1997) 4327
26. Dieter R.K. Tetrahedron 55 (1999) 4177 provides a review of the reaction of acyl chlorides with organometallic reagents
27. Tan L.K., and Brownstein S. J. Org. Chem. (1983) 302
28. Bigi F., Casnati G., Sartori G., and Pridieri G. J. Chem. Soc., Perkin Trans. 2 (1991) 1319
29. Brown H.C., and Jensen F.R. J. Am. Chem. Soc. 83 (1958) 2291
30. Brown H.C., Marino G., and Stock L.M. J. Am. Chem. Soc. 84 (1959) 3310
31. 4
32. Olah G.A., and Kobayashi S. J. Am. Chem. Soc. 93 (1971) 6964
33. Olah G.A., Tashiro M., and Kobayashi S. J. Am. Chem. Soc. 92 (1970) 6371
34. Olah G.A. Acc. Chem. Res. 4 (1971) 240
35. DeHaan F.P., Covey W.D., Delker G.L., Baker N.J., Feigon J.F., Miller K.D., and Stelter E.D. J. Am. Chem. Soc. 101 (1979) 1336
36. Santiago C., Houk K.N., and Perrin C.L. J. Am. Chem. Soc. 101 (1979) 1337
37. Padgett, L. W. Ph.D. Dissertation, Clemson University, 2005.
38. Kimbaris A., and Varvounis G. Tetrahedron 56 (2000) 9675
39. Song C., Knight D.W., and Whatton M.A. Tetrahedron Lett. 45 (2004) 9573
40. Song C., Knight D.W., and Whatton M.A. Org. Lett. 8 (2006) 163
41. Cadamuro S., Degani I., Dughera S., Fochi R., and Gatti A. J. Chem. Soc., Perkin Trans. 1 (1993) 273
42. Knight L.W., Huffman J.W., and Isherwood M.L. Synlett (2003) 1993
43. Chen Q., Wang T., Zhang Y., Wang Q., and Ma J. Synth. Commun. 32 (2002) 1041