Synthesis and purification of 3-N-acylaminopyrazolinones using a sequence of functionalized polymers

Tetrahedron Letters

Volumn 44, Issue 19, 2003, Pages 3843-3845

  Fu, Jiasheng ^a   Shuttleworth, Stephen J ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 N ACYLAMINOPYRAZOLINONE; CHEMICAL COMPOUND; POLYMER; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL PROCEDURES; PURIFICATION; STOICHIOMETRY; SYNTHESIS;

EID: 0037420788     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00738-X     Document Type: Article

References (11)

1. For a review, see: Wiley, R. H.; Wiley, P. Pyrazolones, Pyrazolidones and Derivatives; Weissberger, A., Ed.; Interscience: New York, 1964; Chapter VIII., Volume 20 of the Series The Chemistry of Heterocyclic Compounds.
2. Cocco M.T., Congiu C., Onnis V. J. Het. Chem. 31:1994;925.
3. Elgemeie G.E.H., Elghandour A.H., Elzanate A.M. J. Chem. Res. Synop. 7:1997;256.
4. Vanden Eynde J.J., Rutot D. Tetrahedron. 55:1999;2687.
5. Barr C.R., Salminen I.F., Weissberger A. J. Am. Chem. Soc. 73:1951;4131.
6. Graham B., Porter H.D., Weissberger A. J. Am. Chem. Soc. 71:1949;983.
7. Polymer-supported Hünig's base was purchased from Polymer Laboratories Ltd., catalogue # 3413-4679. Polymer-supported N-methylmorpholine and 4-dimethylaminopyridine were both purchased from Argonaut Technologies Inc., catalogue # 800282 and # 800288, respectively.
8. Polymer-supported sulfonic acid is commercially-available from Polymer Laboratories Ltd., catalogue # 3404-4679.
9. N-(2-Aminoethyl)aminomethylpolystyrene is commercially available from Novabiochem Inc., catalogue # 01-64-0178.
10. 2 requires 217.23.
11. As a typical example, for Table 1, entry 2, treatment of 8 with methanolic ammonia enabled 27% of amine 1 to be recycled, corresponding to a 63% overall account of mass balance; the loss of material in this experiment is attributed to sub-optimal resin washing in step 3.