A Versatile Route to 2-Arylmethyl-1,2,4-oxadiazolidine-3,5-diones via Regiospecific Alkylation of 1,2,4-Oxadiazolidine-3,5-dione

Synlett

Volumn 1997, Issue 3, 1997, Pages 263-264

  Cantello, Barrie C C ^a   Connor, Susan C ^a   Dean, David K ^a   Hindley, Richard M ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542421242     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-772     Document Type: Article

References (15)

1. Kraus, J.L.; Pharmacological Research Communication 1983, 15, 119.
2. See (a) Shinozaki, H.; Konishi, S. Neuropharmacology 1974, 13, 665. (b) Evans, R.H.; Francis, A.A.; Hunt, K.; Martin, M.R.; Watkins, J.C. J. Pharm. Pharmac. 1978, 30, 364. (c) Vankatraman, S.; Boon, R.J.; Schulte, M.K.; Koerner, J.F.; Johnson, R.L. J. Med. Chem. 1994, 37, 3939.
3. See (a) Shinozaki, H.; Konishi, S. Neuropharmacology 1974, 13, 665. (b) Evans, R.H.; Francis, A.A.; Hunt, K.; Martin, M.R.; Watkins, J.C. J. Pharm. Pharmac. 1978, 30, 364. (c) Vankatraman, S.; Boon, R.J.; Schulte, M.K.; Koerner, J.F.; Johnson, R.L. J. Med. Chem. 1994, 37, 3939.
4. See (a) Shinozaki, H.; Konishi, S. Neuropharmacology 1974, 13, 665. (b) Evans, R.H.; Francis, A.A.; Hunt, K.; Martin, M.R.; Watkins, J.C. J. Pharm. Pharmac. 1978, 30, 364. (c) Vankatraman, S.; Boon, R.J.; Schulte, M.K.; Koerner, J.F.; Johnson, R.L. J. Med. Chem. 1994, 37, 3939.
5. Very recently a synthesis of (S)-quisqualic acid 2 via the nucleophilic ring-opening of an optically active aziridine by 1 has been reported by Baldwin's group: Farthing, C.N.; Baldwin, J.E.; Russell, A.T.; Schofield, C.J.; Spivey, A.L. Tetrahedron Letters. 1996, 37, 5225.
6. Lipinski, C.A.; Fiese, E.F.; Korst, R.J. Quant. Struct.-Act. Relat. 1991, 10, 109.
7. (a) Goldstein, S.W.; McDermott, R.E.; Gibbs, E.M.; Stevenson, R.W. J. Med. Chem. 1993, 36, 2238.
8. (b) Patent WO9203425 (Pfizer), Chem. Abstr. 1992, 117, 26553s.
9. (a) US Patent 5,480,896 (American Home Products), Chem. Abstr. 1996; 124, 232471;
10. (b) US Patent 5,420,146 (American Home Products), Chem. Abstr. 1995 123, 112068.
11. Japanese Patent 08059638 (Yamanouchi), Chem. Abstr. 1996, 125, 10826.
12. Renaut, P.; Thomas, D.; Bellamy, F.D. Synthesis 1991, 265.
13. Satisfactory microanalysis and spectroscopic data were obtained for all new compounds.
14. Compound 18 has also been prepared by workers at American Home Products (reference 6a) building up the 1,2,4-oxadiazolidine-3,5-dione ring in a stepwise manner similar to that outlined in Scheme 1. The compounds prepared by the two routes have similar mps (157-8°C and 155-7°C respectively).
15. Cantello, B.C.C.; Cawthorne, M.A.; Cottam, G.P.; Duff, P.T.; Haigh, D.; Hindley, R.M.; Lister, C.A.; Smith, S.A.; Thurlby, P.L. J. Med. Chem., 1994, 37, 3977.