The synthesis of 2-ketopiperazine acetic acid esters and amides from ethylenediamines with maleates and maleimides

Tetrahedron Letters

Volumn 44, Issue 9, 2003, Pages 1823-1826

  Abelman, Matthew M ^a   Fisher, Karl J ^a   Doerffler, Edward M ^a   Edwards, Paul J ^b  

^a Signature BioScience Inc   (United States)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

Dimethyl fumarate; Dimethyl maleate; Ethylenediamine; Ketopiperazine

Indexed keywords

AMIDE; ETHYLENEDIAMINE DERIVATIVE; FUMARIC ACID DERIVATIVE; MALEIC ACID DERIVATIVE; MALEIMIDE DERIVATIVE; PIPERAZINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DIASTEREOISOMER; DRUG SYNTHESIS; EPIMERIZATION; MICHAEL ADDITION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY;

EID: 0037463521     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00103-5     Document Type: Article

References (16)

1. Shreder K., Zhang L., Gleeson J.-P., Ericsson J.A., Venkatachalapathi V.Y., Goodman M. J. Comb. Chem. 1:1999;383.
2. Dinsmore C.J., Bergman J.M., Bogusky M.J., Culberson J.C., Hamilton K.A., Graham S.L. Org. Lett. 3:2001;865.
3. Petasis N.A., Patel Z.D. Tetrahedron Lett. 41:2000;9607.
4. Beshore D.C., Dinsmore C.J. Org. Lett. 4:2002;1201.
5. Dinsmore C.J., Zartman C.B. Tetrahedron Lett. 41:2000;6309.
6. Cheng J.-F., Chen M., Arrhenius T., Nadzan A. Tetrahedron Lett. 43:2002;6293.
7. Gurjar M.K., Karmakar S., Mohapatra D.K., Phalgune U.D. Tetrahedron Lett. 43:2002;1897.
8. Phillips, A. P. US Pat. 2,958,693, 1960; Chem. Abstr. 1961, 55, 9437i Sheremeteva, T. V.; Sharifov, G. S.; Romashkova, K. A. Dokl. Akad. Nauk SSSR 1968, 182, 859; Chem. Abstr. 1969, 70, 37783d.
9. Masuzawa K., Masaki M., Ohta M. Chem. Pharm. Bull. 14:1966;194.
10. Sharma S., Bindra R., Iyer R.N., Anand N. J. Med. Chem. 18:1975;913.
11. Cantatore G., Borzatta V. Chem. Abstr. 111:1989;116279n.
12. Gubert S., Braojos C., Anglada L., Bolos J., Sacristan A., Ortiz J.A. J. Heterocyclic Chem. 30:1993;275.
13. Sheremeteva T.V., Kudryavtsev V.V. Izv. Akad. Nauk SSSR Ser. Khim. 2:1966;289.
14. Cave C.., Gassama A., Mahuteau J., d'Angelo J., Riche C. Tetrahedron Lett. 38:1997;4773.
15. -1. Generally speaking, ketopiperazines with a secondary amide tended to be solids. The ketopiperazines with a tertiary amide tended to be oils that were easily purified by silica gel chromatography using 10% methanol/ethyl acetate as eluent.
16. -1.