A novel traceless solid-phase Friedländer synthesis

Organic Letters

Volumn 5, Issue 17, 2003, Pages 3061-3063

  Patteux, Claudine ^a   Levacher, Vincent ^a   Dupas, Georges ^a  

^a IRISA   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE; KETONE DERIVATIVE; POLYMER; QUINOLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; SOLID;

EID: 0141855373     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035049z     Document Type: Article

References (15)

1. Franzén, R. G. J. Comb. Chem. 2000, 2, 195.
2. (a) Cheng, C. C.; Yan, S. J. Organic Reactions; John Wiley and Sons: New York, 1982; Vol. 28, p 37.
3. (b) Dormer, P. G.; Eng, K. K.; Farr, R. N.; Humphrey, G. R.; McWilliams, J. C.; Reider, P. J.; Sager, J. W.; Volante, R. P. J. Org. Chem. 2003, 467.
4. (a) Friedländer, P.; Henriques, S. Chem. Ber. 1882, 15, 2572.
5. (b) McGeachin, S. G. Can. J. Chem. 1966, 44, 2323.
6. (c) Abert, A.; Yamamoto, H. J. Chem. Soc B 1966, 956.
7. (a) Borsche, W.; Ried, W. Liebigs Ann. Chem. 1943, 554, 269.
8. (b) Borsche, W.; Barthenheier, J. Liebigs Ann. Chem. 1941, 548, 50.
9. Porter, H. K. Org. React. 1973, 20, 455.
10. For reviews on cyclative cleavage strategies, see: (a) van Maarseveen, J. H. Comb. Chem. High Throughput Screening 1998, 1, 185. (b) Tzschucke, C. C.; Market, C.; Bannwarth, W.; Roller, S.; Hebel, A.; Haag, R. Angew. Chem., Int. Ed. 2002, 41, 3964. (c) Park, K. H.; Kurth, M. J. Drug Future 2000, 25, 1265. (d) Blaney, P.; Grigg, R.; Sridharan, V. Chem. Rep. 2002, 102, 2607.
11. For reviews on cyclative cleavage strategies, see: (a) van Maarseveen, J. H. Comb. Chem. High Throughput Screening 1998, 1, 185. (b) Tzschucke, C. C.; Market, C.; Bannwarth, W.; Roller, S.; Hebel, A.; Haag, R. Angew. Chem., Int. Ed. 2002, 41, 3964. (c) Park, K. H.; Kurth, M. J. Drug Future 2000, 25, 1265. (d) Blaney, P.; Grigg, R.; Sridharan, V. Chem. Rep. 2002, 102, 2607.
12. For reviews on cyclative cleavage strategies, see: (a) van Maarseveen, J. H. Comb. Chem. High Throughput Screening 1998, 1, 185. (b) Tzschucke, C. C.; Market, C.; Bannwarth, W.; Roller, S.; Hebel, A.; Haag, R. Angew. Chem., Int. Ed. 2002, 41, 3964. (c) Park, K. H.; Kurth, M. J. Drug Future 2000, 25, 1265. (d) Blaney, P.; Grigg, R.; Sridharan, V. Chem. Rep. 2002, 102, 2607.
13. For reviews on cyclative cleavage strategies, see: (a) van Maarseveen, J. H. Comb. Chem. High Throughput Screening 1998, 1, 185. (b) Tzschucke, C. C.; Market, C.; Bannwarth, W.; Roller, S.; Hebel, A.; Haag, R. Angew. Chem., Int. Ed. 2002, 41, 3964. (c) Park, K. H.; Kurth, M. J. Drug Future 2000, 25, 1265. (d) Blaney, P.; Grigg, R.; Sridharan, V. Chem. Rep. 2002, 102, 2607.
14. Gordon, K. H.; Balasubramanian S. Org. Lett. 2001, 3, 53.
15. During the cyclative cleavage process, the resulting resin 6 may react with ketones 2 still present in solution to give the corresponding imines. To ensure the complete removal of ketones 2a-f, which could have been scavenged, the recovered resin 6 was thus treated under acidic conditions (2 M HCl/THF/water) prior to regenerating resin 1b.