An efficient synthesis of tetrasubstituted imidazoles from N-(2-Oxo)- amides

Tetrahedron Letters

Volumn 39, Issue 49, 1998, Pages 8939-8942

  Claiborne, Christopher F ^a   Liverton, Nigel J ^a   Nguyen, Kevin T ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMMONIUM DERIVATIVE; IMIDAZOLE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0032481025     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02058-9     Document Type: Article

References (11)

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2. (b) J. C. Lee, U. Prabhakar, D. E. Griswold, D. Dunnington, P. R. Young, A. Badger Circulatory Shock , 1995, 44, 97.
3. 2. (a) R. Gompper; Chem. Ber. 1957, 90 , 374.
4. (b) E. Beccalli, L. Majori, A. Marchesini, C. Torricelli, Chem. Lett. 1980, 657.
5. (c) H. Alper, S. Amaratunga, J. Org. Chem. 1982, 47, 3595.
6. 3. Substitution of ammonium trifluoroacetate with ammonium acetate lead to decomposition of starting materials. The subdued nucleophilicity of the trifluoroacetate anion results in conditions sufficiently mild to accommodate the fluoropyridine moiety.
7. 4. (a) M. R. Grimmett in Advances in Heterocyclic Chemistry; A. R. Katritzky, A. J. Boulton, Ed.; Academic Press: New York, 1970; Vol 12, p 103.
8. (b) M. R. Grimmett in Advances in Heterocyclic Chemistry; A. R. Katritzky, A. J. Boulton, Ed.; Academic Press: New York, 1980, Vol 27, p 241.
9. 5. The use of these reaction conditions resulted in the decomposition of starting materials. The sole isolated product was characterized as the imidazole pyridone. We suggest that the pyridone is formed via acetate addition to the fluropyridine followed by hydrolysis upon aqueous work up. (formula presented)
10. 2 groups was difficult due to competitive acylation on oxygen (with the exception of acetyl chloride (entry 9)). Attempts to migrate the acyl group in the ester products to nitrogen were unsuccessful.
11. 7. Relative stereochemistry was assigned by formation of the oxazolidinone with phosgene and determined by NOE.