Novel one-pot microwave assisted Gewald synthesis of 2-acyl amino thiophenes on solid support

Synlett

Volumn , Issue 1, 2003, Pages 63-66

  Frutos Hoener, Annabelle P ^a   Henkel, Bernd ^b   Gauvin, Jean Christophe ^a  

^a Morphochem AG Basel   (Switzerland)

^b Morphochem AG   (Germany)

Author keywords

Acylations; Combinatorial chemistry; Gewald synthesis; Microwave chemistry; Solid phase thiophene synthesis

Indexed keywords

THIOPHENE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL REACTION; MICROWAVE RADIATION; SYNTHESIS;

EID: 0037238407     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (17)

1. Gewald, K. Angew. Chem. 1961, 73, 114.
2. Sabnis, R. W.; Rangnekar, D. W.; Sonawane, N. D. J. Heterocycl. Chem. 1999, 36, 333.
3. Buchstaller, H.-P.; Siebert, C. D.; Lyssy, R. H.; Frank, I.; Duran, A.; Gottschlich, R.; Noe, C. R. Monatsh. Chem. 2001, 132, 279.
4. Castanedo, G. M.; Sutherlin, D. P. Tetrahedron Lett. 2001, 42, 7181.
5. Pinto, I. L.; Jarvest, R. L.; Serafinowska, H. T. Tetrahedron Lett. 1999, 41, 1597.
6. Koike, K.; Jia, Z.; Nikaido, T.; Liu, Y.; Zhao, Y.; Guo, D. Org. Lett. 1999, 1, 197.
7. Gottschlich, R.; Leibrock, J.; Noe, C. R.; Berger, M.; Buchstaller, H.-P. Eur. Pat. Appl. EP 717044, 1996; Chem. Abstr. 1996, 125, 114585.
8. Modica, M.; Santiagati, M.; Russo, F.; Parotti, L.; Gioia, L. D.; Selvaggini, C.; Salmona, M.; Mennini, T. J. Med. Chem. 1997, 40, 574.
9. Gutschow, M.; Kuerschner, L.; Neumann, U.; Peitsch, M.; Loser, R.; Koglin, N.; Eger, K. J. Med. Chem. 1999, 42, 5437.
10. Iversen, L. F.; Anderson, H. S.; Branner, S.; Mortensen, S. B.; Peters, G. H.; Norris, K.; Olsen, O. H.; Jeppesen, C. B.; Lundt, B. F.; Ripka, W.; Moller, K. B.; Moller, N. P. H. J. Biol. Chem. 2000, 275, 10300.
11. Webb, T. R.; Melman, N.; Ji, X.; Jacobson, K. A. Chem. Lett. 2000, 10, 31.
12. Fujita, M.; Hirayama, T.; Ikeda, N. Bioorg. Med. Chem. 2002, 10, 3113.
13. McKibben, B. P.; Cartwright, C. H.; Castelhano, A. L. Tetrahedron Lett. 1999, 40, 5471.
14. Arya, V. P.; Ghate, S. P. Indian J. Chem. 1971, 9, 1209.
15. Peet, N. P.; Sunder, S.; Barbuch, R. J. J. Heterocycl. Chem. 1985, 23, 129.
16. 2:TFA to obtain 37 mg of the acylated thiophene (90% yield) after filtration and evaporation.
17. 6): δ = 165.94, 160.28, 154.44, 145.225, 140.25, 136.28, 129.81, 129.65, 129.49, 126.08, 114.72, 62.32, 54.96, 34.027, 15.02.