A new and efficient multicomponent solid-phase synthesis of 2-acylaminomethylthiazoles

Tetrahedron Letters

Volumn 44, Issue 18, 2003, Pages 3679-3682

  Henkel, Bernd ^a   Sax, Michael ^b   Dömling, Alexander ^a  

^a Morphochem AG   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 (N,N DIMETHYLAMINO) 2 ISOCYANOACRYLATE; ALDEHYDE DERIVATIVE; ALIPHATIC CARBOXYLIC ACID; AMIDE; AMINE; AROMATIC CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; CYANOACRYLATE DERIVATIVE; RESIN; THIAZOLE DERIVATIVE; THIOCARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL COMPOSITION; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MULTICOMPONENT REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; SYNTHESIS;

EID: 0037471469     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00662-2     Document Type: Article

References (17)

1. Pettit G.R., Kamano Y., Tuinman A.A., Herald C.L., Baczynskyj L., Schmidt J.M., Boettner F.E., Kizu H., Tomer K.B., Bontems R.J. J. Am. Chem. Soc. 109:1987;6883-6885.
2. Bycroft B.W., Gowland M.S. J. Chem. Soc., Chem. Commun. 1978;256-258.
3. Hara M., Takahashi I., Yoshida M., Asano K., Kawamoto I., Morimoto M., Nakano H. J. Antibiot. 42:1989;333.
4. For a review, see: Konz D., Marahiel M.A. Chem. Biol. 6:1999;R39-R48.
5. Nuss J.M., Wagman A.S. Annu. Rep. Med. Chem. 35:2000;211-220.
6. Rami H.K., Smith S.A. Exp. Opin. Ther. Pat. 10:2000;623-634.
7. El Kazzouli S., Berteina-Raboin S., Mouaddib A., Guillaumet G. Tetrahedron Lett. 43:2002;3193-3196.
8. Baer R., Masquelin T. J. Comb. Chem. 3:2001;16-19.
9. Pons J.-F., Mishir Q., Nouvet A., Brookfield F. Tetrahedron Lett. 41:2000;4965-4968.
10. Goff D., Fernandez J. Tetrahedron Lett. 40:1999;423-426.
11. Heck S., Dömling A. Synlett. 2000;424-426.
12. For other applications of 3-(N,N-dimethylamino)-2-isocyanoacrylates, see: (a) Lau, H.; Schöllkopf, U. Liebigs Ann. Chem. 1982, 2093-2095; (b) Bienaymé, H.; Bouzid, K. Tetrahedron Lett. 1998, 39, 2735-2738; (c) Bienaymé, H. Tetrahedron Lett. 1998, 39, 255-4258; (d) Heldal, C. J.; Lucas, J. C. Org. Lett. 2002, 4, 4133-4134.
13. For other applications of 3-(N,N-dimethylamino)-2-isocyanoacrylates, see: (a) Lau, H.; Schöllkopf, U. Liebigs Ann. Chem. 1982, 2093-2095; (b) Bienaymé, H.; Bouzid, K. Tetrahedron Lett. 1998, 39, 2735-2738; (c) Bienaymé, H. Tetrahedron Lett. 1998, 39, 255-4258; (d) Heldal, C. J.; Lucas, J. C. Org. Lett. 2002, 4, 4133-4134.
14. For other applications of 3-(N,N-dimethylamino)-2-isocyanoacrylates, see: (a) Lau, H.; Schöllkopf, U. Liebigs Ann. Chem. 1982, 2093-2095; (b) Bienaymé, H.; Bouzid, K. Tetrahedron Lett. 1998, 39, 2735-2738; (c) Bienaymé, H. Tetrahedron Lett. 1998, 39, 255-4258; (d) Heldal, C. J.; Lucas, J. C. Org. Lett. 2002, 4, 4133-4134.
15. For other applications of 3-(N,N-dimethylamino)-2-isocyanoacrylates, see: (a) Lau, H.; Schöllkopf, U. Liebigs Ann. Chem. 1982, 2093-2095; (b) Bienaymé, H.; Bouzid, K. Tetrahedron Lett. 1998, 39, 2735-2738; (c) Bienaymé, H. Tetrahedron Lett. 1998, 39, 255-4258; (d) Heldal, C. J.; Lucas, J. C. Org. Lett. 2002, 4, 4133-4134.
16. Kolb, J.; Beck, B.; Herdtweck, Dömling, A., unpublished results.
17. 3): δ 171.6, 167.5, 161.9, 147.1, 134.0, 132.1, 128.9, 127.6, 127.4, 57.0, 52.7, 33.8, 19.8, 18.6.