Regiocontrolled cyclization reaction of N-(2-hydroxyethyl)ureas by transfer of activation: One-pot synthesis of 2-imidazolidinones

Journal of Organic Chemistry

Volumn 64, Issue 8, 1999, Pages 2941-2943

  Kim, Taek Hyeon ^a   Lee, Gue Jae ^a  

^a Chonnam National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

2 IMIDAZOLIDINONE DERIVATIVE; N (2 HYDROXYETHYL)UREA DERIVATIVE; PHOSGENE; PROTEINASE INHIBITOR; SEROTONIN 3 ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; THIN LAYER CHROMATOGRAPHY;

EID: 0000100042     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9820061     Document Type: Article

References (25)

1. (a) Lam, P. Y. S.; Jadhav, P. K.; Eyermann, C. J.; Hodge, C. N.; Ru, Y.; Bacheler, L. T.; Meek, J. L.; Otto, M. J.; Rayner, M. M.; Wong, Y. N.; Chang, C.-H.; Weber, P. C.; Jackson, D. A.; Sharpe, T. R.; Erickson-Viitanen, S. Science 1994, 263, 380.
2. (b) Wilkerson, W. W.; Dax, S.; Cheatham, W. W. J. Med. Chem. 1997, 40, 4079.
3. (c) Patel, M.; Bacheler, L. T.; Rayner, M. M.; Cordova, B. C.; Klabe, R. M.; Erickson-Viitanen, S.; Seitz, S. P. Bioorg. Med. Chem. Lett. 1998, 8, 823.
4. Heidempergher, F.; Pillan, A.; Pinciroli, V.; Vaghi, F.; Arrigoni, C.; Bolis, G.; Caccia, C.; Dho, L.; McArthur, R.; Varasi, M. J. Med. Chem. 1997, 40, 3369.
5. (a) Forbes, I. T.; Ham, P.; Booth, D.; Martin, R. T.; Thompson, M.; Baxter, G. S.; Blackburn, T. P.; Glen, A.; Kennett, G. A.; Wood, M. D. J. Med. Chem. 1995, 38, 2524.
6. (b) Lewis, R. T.; Macleod, A. M.; Merchant, K. J.; Kelleher, F.; Sanderson, I.; Herbert, R. H.; Cascieri, M. A.; Sadowski, S.; Ball, R. G.; Hoogsteen, K. J. Med. Chem. 1995, 38, 923.
7. (a) (4R,5S)-1,5-Dimethyl-4-phenyl-2-imidazolidinone: Guillena, G.; Najera, C. Tetrahedron: Asymmetry 1998, 9, 1125 and references therein.
8. (b) (4S)-4-(1-Methylethyl or phenymethyl)-1-phenyl-2-imidazolidinone: Taguchi, T.; Shibuya, A.; Sasaki, H.; Endo, J.; Morikawa, T.; Shiro, M. Tetrahedron: Asymmetry 1994, 5, 1423 and references therein.
9. (c) trans-4,5-Tetramethylene-2-imidazolidinone: Davies, S. G.; Evans, G. B.; Mortlock, A. A. Tetrahedron: Asymmetry 1994, 5, 585.
10. (d) Camphor-derived 2-imidazolidinone: Palomo, C.; Oiarbide, M.; Gonzalez, A.; Garcia, J. M.; Berree, F. Tetrahedron Lett. 1996, 37, 4565.
11. (e) (4S)-4-Carboxylate-2-imidazolidinone: Kubota, H.; Kubo, A.; Takahashi, M.; Shimizu, R.; Da-te, T.; Okamura, K.; Nunami, K. J. Org. Chem. 1995, 60, 6776.
12. Kim, J.-M.; Wilson T. E.; Norman, T. H.; Schultz, P. G. Tetrahedron Lett. 1996, 37, 5309.
13. Davies, S. G.; Mortlock, A. A. Tetrahedron 1993, 49, 4419.
14. (a) Vorbruggen, H.; Krolikiewicz, K. Tetrahedron 1993, 49, 9353.
15. (b) Burrell, G.; Evans, J. M.; Jones, G. E.; Stemp, G. Tetrahedron Lett. 1990, 31, 3649.
16. Heine, H. W.; Kenyon, W. G.; Johnson, E. M. J. Am. Chem. Soc. 1961, 83, 2570.
17. Helmut, T. Ger. Patent 1,126,392, 1962; Chem. Abstr. 1962, 57, 9859i.
18. Recently, Prasad reported that chiral N-acylated 2g and 2f were prepared from the ring opening of oxazolines with aniline followed by cyclization with phosgene and used for highly diastereoselective benzylations and methylations; see: Konigsberger, K.; Prasad, K.; Repic, O.; Blacklock, T. J. Tetrahedron: Asymmetry 1997, 8, 2347. We found these compounds were readily prepared from a convenient short course via acylation of 2g and 2f, and its results will be published in another paper.
19. (a) Charette, A. B.; Chua, P. J. Org. Chem. 1998, 63, 908.
20. (b) Sisti, N. J.; Foeler, F. W.; Grierson, D. S. Synlett 1991, 816.
21. (c) Sisti, N. J.; Zeller, E.; Grierson, D. S.; Fowler, F. W. J. Org. Chem. 1997, 62, 2093.
22. (d) Thomas, E. W. Synthesis 1993, 767.
23. For a general discussion of the transfer of activation, see: (a) Sobolov, S. B.; Sun, J.; Cooper, B. A. Tetrahedron Lett. 1998, 39, 5685.
24. (b) Eissenstat, M. A.; Weaver, J. D. Tetrahedron Lett. 1995, 36, 2029.
25. Akester, J.; Cui, J.; Fraenkel, G. J. Org. Chem. 1997, 62, 431.