Solution-phase parallel oxazole synthesis with TosMIC

Tetrahedron Letters

Volumn 40, Issue 30, 1999, Pages 5637-5638

  Kulkarni, Bheemashankar A ^a   Ganesan, A ^a  

^a INSTITUTE OF MOLECULAR AND CELL BIOLOGY   (Singapore)

Author keywords

Combinatorial chemistry; Isocyanides; Oxazoles; Supported reagents reactions

Indexed keywords

OXAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MINIMUM INHIBITORY CONCENTRATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID PHASE EXTRACTION;

EID: 0033165871     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01050-3     Document Type: Article

References (14)

1. For recent reviews, see: (a) Lamberth, C. J. Praktische Chem. 1998, 340, 483-485.
2. (b) van Leusen, A. M.; van Leusen, D. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; Wiley: New York, 1995; Vol. 7, pp 4973-4979.
3. Kulkarni, B. A.; Ganesan, A., preceding paper in this issue.
4. van Leusen, A. M.; Hoogenboom, B. E.; Siderius, H. Tetrahedron Lett. 1972, 2369-2372.
5. For recent examples, see: (a) Anderson, B. A.; Becke, L. M.; Booher, R. N.; Flaugh, M. E.; Harn, N. K.; Kress, T. J.; Varie, D. L.; Wepsiec, J. P. J. Org. Chem. 1997, 62, 8634-8639.
6. (b) Crowe, E.; Hossner, F.; Hughes, M. J. Tetrahedron 1995, 57, 8889-8900.
7. (c) Horne, D. A.; Yakushijin, K.; Büchi, G. Heterocycles 1994, 39, 139-153.
8. (d) Crozet, M. P.; Sabuco, J.-F.; Tamburlin, I.; Barreau, M.; Giraud, L.; Vanelle, P. Heterocycles 1993, 36, 45-54.
9. (e) Oussaid, B.; Hubert, C.; Fayet, J. P.; Garrigues, B. Bull. Soc. Chim. Fr. 1993, 130, 86-92.
10. For examples of solution-phase library synthesis utilizing ion exchange resins, see: (a) Gayo, L. M. Biotech. Bioeng. (Combinatorial Chem.) 1998, 61, 95-106.
11. (b) Kulkarni, B. A.; Ganesan, A. Angew. Chem. Int. Ed. Engl. 1997, 36, 2454-2455.
12. (c) Kulkarni, B. A.; Ganesan, A. Chem. Commun. 1998, 785-786.
13. van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153-1159.
14. Typical procedure: A solution of aldehyde (0.135 mmol) and TosMIC (1.1 mol equiv) in 1:1 DME/MeOH (4 mL) was refluxed with Ambersep 900 OH resin (250 mg, Fluka, exchange capacity 0.95 meq/mL) for 8 h. The reaction mixture was filtered, the resin washed (MeOH, 3 × 10 mL), and the combined filtrates concentrated. The crude products were purified by preparative TLC (10-30 % EtOAc/hexanes eluent).