1-[2'-(trimethylsilyl)ethoxymethyl]-2-phenylsulfonylimidazole: A new reagent for the preparation of C-4 substituted imidazoles

Tetrahedron Letters

Volumn 38, Issue 45, 1997, Pages 7835-7838

  Phillips, James G ^a   Fadnis, Leena ^a   Williams, David R ^b  

^a GUILFORD PHARMACEUTICALS INC   (United States)

^b INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [2' (TRIMETHYLSILYL)ETHOXYMETHYL] 2 PHENYLSULFONYLIMIDAZOLE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; DIAGNOSTIC VALUE; METAL BINDING; PROTON TRANSPORT; REACTION ANALYSIS; RECEPTOR BINDING; X RAY CRYSTALLOGRAPHY;

EID: 0030727524     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10128-9     Document Type: Article

References (15)

1. For an overview: Grimmett, M.R. Imidazoles, In Comprehensive Heterocyclic Chemistry II, Editors; A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Vol. 3 (I. Shinkai) 1996, pages 77-220.
2. Shapiro, G.; Gomez-Lor, B. J. Org. Chem. 1994, 59, 5524.
3. Iddon, B. Heterocycles 1985, 23, 417.
4. Katritzky, A.R.; Slawinski, J.J.; Brunner, F. J. Chem. Soc. Perkin I, 1989, 1139.
5. Rewcastle, G.W.; Katritzky, A.R. Adv. Heterocycl. Chem. 1993, 56, 155.
6. Suzuki, M.; Tanaka, H.; Miyasaka, T. Chem. Pharm. Bull. 1987, 35, 4056.
7. Lipshutz, B.H.; Huff, B.; Hagen, W. Tetrahedron Lett. 1988, 28, 3411.
8. Achab, S.; Guyot, M.; Potier, P. Tetrahedron Lett. 1995, 36, 2615.
9. Complete X-ray diffraction data for the single crystal analysis of 4 have been deposited with the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK. We gratefully thank Professor Henry Rapoport for his assistance in facilitating this diffraction study.
10. 3): 8.03 (m, 2H), 7.62 (m, 2H), 7.54 (m, 3H), 7.23 (s, 1H), 5.75 (s, 2H), ,3.52 (m, 2H), 0.80 (m, 2H), 0.05 (s, 9H).
11. 1H NMR information to distinguish C-4 and C-5 isomers: Matthews, D.P.; Whitten, J.P.; McCarthy, J.R. J. Heterocyclic Chem. 1987, 24, 689.
12. Turner, R.M.; Lindell, S.D.; Ley, S.V. J. Org. Chem. 1991, 5739.
13. 3) for selected products: Compound 1: δ 8.06 (m, 2H), 7.60 (m, 1H), 7.53 (m, 2H), 7.16 (d, 2H), 5.70 (s, 2H), 3.44 (m, 2H), 0.81 (m, 2H), -0.05 (s, 9H). Compound 5 (Table 1): δ 8.6 (d, 2H), 8.02 (m, 2H), 7.66 (m, 1H), 7.56 (m, 2H), 7.32 (d, 2H), 6.76 (s, 1H), 5.90 (br s, 1H), 5.75 (AB quartet, 2H), 4.12 (m, 1H), 3.66 (m, 2H), 0.90 (m, 2H), 0.05 (s, 9H). Compound 6 (Table 1): δ 9.84 (s, 1H), 8.09 (m, 2H), 7.78 (s, 1H), 7.67 (m, 1H), 7.56 (m, 2H), 6.18 (s, 2H), 3.53 (m, 2H), 0.80 (m, 2H), -0.05 (s, 9H). Compound 7 (Table 1): δ 8.02 (m, 2H), 7.60 (m, 1H), 7.52 (m, 2H), 6.90 (s, 1H), 5.66 (s, 2H), 3.51 (m, 2H), 2.60 (t, 2H), 1.68 (m, 6H), 1.53 (m, 2H), 1.18 (m, 4H), 0.88 (m, 1H), 0.82 (m, 2H). Compound 9 (Table 1): δ 8.0 (m, 2H), 7.59 (m, 1H), 7.50 (m, 2H), 7.02 (s, 1H), 5.62 (s, 2H), 3.93 (m, 4H), 3.41 (m, 2H), 2.58 (br s, 1H), 1.96 (m, 4H), 0.78 (m, 2H), 0.05 (s, 9H). Compound 12: δ 8.04 (m, 2H), 7.62 (m, 1H), 7.52 (m, 2H), 7.39 (s, 1H), 5.64 (s, 1H), 3.41 (m, 2H), 0.80 (m, 2H), 0.19 (s, 9H), -0.03 (s, 9H). Compound 14: δ 7.50 (d, 1H, J = 1.2 Hz), 6.88 (d, 1H, J = 1.2 Hz), 5.20 (s, 2H), 3.93 (m, 4H), 3.45 (m, 2H), 2.02 (m, 4H), 0.88 (m, 2H), 0.05 (s, 9H).
14. a) Cliff, M.; Pyne, S.G. J. Org. Chem. 1997, 62, 1023.
15. b) Sonogashira, K. In Comprehensive Organic Synthesis, Trost, B.M.; Fleming, I., Eds., Pergamon Press: New York, 1991, Vol. 3, p. 521.