Alkylation of an imidazolidine enaminoester: A new sequence for the c(α)-alkylation of 4,5-dihydroimidazoles

Tetrahedron

Volumn 53, Issue 34, 1997, Pages 11781-11790

  Jones, Raymond C F ^a   Patel, Pravin ^a   Hirst, Simon C ^b   Turner, Ian ^b  

^a OPEN UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

IMIDAZOLE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030811539     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00752-7     Document Type: Article

References (18)

1. (a) Anderson, M. W.; Begley, M. J.; Jones, R. C. F.; Saunders, J. J. Chem. Soc., Perkin Trans. 1 1984, 2599-2602;
2. (b) Anderson, M. W.; Jones, R. C. F.; Saunders, J. J. Chem. Soc., Perkin Trans. 1 1986, 205-209;
3. (c) Jones, R. C. F.; Anderson, M. W.; Smallridge, M. J. Tetrahedron Lett. 1988, 29, 5001-5004;
4. (d) Jones, R. C. F.; Schofield, J. J. Chem. Soc., Perkin Trans. 1 1990, 375-383;
5. (e) Jones, R. C. F.; Smallridge, M. J.; Chapleo, C. B. J. Chem. Soc., Perkin Trans. 1 1990, 385-391.
6. See, for example: Grout, R. J. in The Chemistry of Amidines and Imidates; Patai, S. Ed.; Wiley. London, 1975, p. 255 et seq.; Chapleo, C. B. Chem. Br. 1986, 313-314.
7. See, for example: Grout, R. J. in The Chemistry of Amidines and Imidates; Patai, S. Ed.; Wiley. London, 1975, p. 255 et seq.; Chapleo, C. B. Chem. Br. 1986, 313-314.
8. See, for example: Saier, M. H. Enzymes in Metabolic Pathways; Harper & Row: New York, 1990; pp.83-85.
9. For other studies with heterocyclic ketene aminals, see: Yu, C.-Y.; Wang, L.-B.; Li, W.-Y.; Huang, Z.-T. Synthesis 1996, 959-962, and refs. therein.
10. For a preliminary report of this work, see: Jones, R. C. F.; Hirst, S. C.; Turner, I. J. Chem. Soc., Perkin Trans. I 1991, 953-954.
11. (a) Jones, R. C. F.; Anderson, M. W.; Smallridge, M. J. Tetrahedron Lett. 1988, 29, 5001-5004;
12. (b) Jones, R. C. F.; Hirst, S. C. Tetrahedron Lett. 1989, 30, 5361-5364.
13. Cf. Wang, L.-B.; Yu, C.-Y.: Huang, Z.-T. Synthesis 1994, 1441-1444. These authors report N-alkylation of N-unsubstituted ketene aminals with ethyl bromoacetate using a different solvent (DMF vs. THF), but make a comment on the importance of the reaction medium; retention of the H-bonded enaminocarbonyl tautomer is observed, in contrast to the β-iminocarbonyl tautomer found in our jV-benzy! example .
14. For related lactones, see: Jones, R. C. F.; Hirst, S. C. Tetrahedron Lett. 1989, 30, 5365-5368.
15. Anderson, M. W.: Jones, R. C. F.; Saunders, J. J. Chem. Soc., Perkin Trans. 1 1986, 1995-1998.
16. Cf. Jones, R. C. F.; Turner, I.; Howard, K. J. Tetrahedron Lett. 1993, 34, 6329-6332.
17. See, for example: Derome, A. E. Modern NMR Techniques for Chemistry Research; Pergamon: Oxford, 1987; pp. 143-151.
18. Kofron, W. G.; Baclawski, L. M. J. Org. Chem. 1976, 41, 1879-1880.