Imidazole Transfer from 1,1′-Carbonyldimidazole and 1,1′-(Thiocarbonyl)diimidazole to Alcohols. A New Protocol for the Conversion of Alcohols to Alkylheterocycles

Journal of Organic Chemistry

Volumn 62, Issue 21, 1997, Pages 7319-7323

  Totleben, Michael J ^a   Freeman, Jeremiah P ^a   Szmuszkovicz, Jacob ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' (THIOCARBONYL)DIIMIDAZOLE; ALCOHOL DERIVATIVE; CARBONYLDIIMIDAZOLE; CIMETIDINE; CLOTRIMAZOLE; ETOMIDATE; HETEROCYCLIC COMPOUND; HISTAMINE; HISTIDINE; IMIDAZOLE DERIVATIVE; KETOCONAZOLE; MICONAZOLE; UNCLASSIFIED DRUG;

ALCOHOL METABOLISM; ARTICLE; CARBON DIOXIDE MEASUREMENT; CHEMICAL REACTION KINETICS; DRUG ELIMINATION; DRUG MECHANISM; ORGANIC CHEMISTRY; REACTION ANALYSIS;

EID: 0030864333     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9708811     Document Type: Article

References (21)

1. For a review of the chemistry of imidazoles, see: Katritzky, A. R.; Rees, C. W. Comprehensive Heterocyclic Chemistry; Potts, K. T., Ed.; Pergamon: New York, 1984; Vol. 5, Part 4A, p 345, 373, 457.
2. For a review of medicinally important imidazoles, see: Roth, H. J.; Kleeman, A. Pharmaceutical Chemistry; John Wiley: New York, 1988; p 218.
3. For reviews of GDI and TCDI, see: (a) Staab, H. A. Angew. Chem., Int. Ed. Engl. 1962, 1, 351. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: New York, 1995; Vol. 7, p 1006, 4862.
4. For reviews of GDI and TCDI, see: (a) Staab, H. A. Angew. Chem., Int. Ed. Engl. 1962, 1, 351. (b) Staab, H. A.; Rohr, W. In Newer Methods of Preparative Organic Chemistry; Foerst, W., Ed.; Academic Press: New York, 1968; Vol. 5, p 61. (b) Staab, H. A.; Rohr, W. In Newer Methods of Preparative Organic Chemistry; Foerst, W., Ed.; Academic Press: New York, 1968; Vol. 5, p 61.
5. For reviews of GDI and TCDI, see: (a) Staab, H. A. Angew. Chem., Int. Ed. Engl. 1962, 1, 351. (b) Staab, H. A.; Rohr, W. In Newer Methods of Preparative Organic Chemistry; Foerst, W., Ed.; Academic Press: New York, 1968; Vol. 5, p 61. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: New York, 1995; Vol. 7, p 1006, 4862. Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A., Ed.; John Wiley: New York, 1995; Vol. 7, p 1006, 4862.
6. Rigo, B.; Kolocouris, N. J. Heterocycl. Chem. 1983, 20, 893.
7. (a) Barton, D. H. R.; McCombie, S. W. J. Chem. Soc., Perkin Trans. 1 1975, 1574.
8. (b) Barton, D. H. R.; Motherwell, W. B. Pure Appl. Chem. 1981, 53, 15 and references cited therein.
9. Compound previously reported: Hirsch, K. S.; Jones, C. D.; Taylor, H. M. U.S. Patent 4 659 730, 1987.
10. 1H NMR spectrum matches Sadtler Standard Spectra 18210M (1974).
11. Hagiwara, H.; Ohtsubo, S.; Kato, M. Tetrahedron 1997, 53, 2415.
12. 4,4′-Dimethoxybenzhydrol (5%) was recovered.
13. Compound previously reported: Baggaley, K. H.; Heald, M.; Hindley, R. M.; Morgan, B.; Tee, J. L.; Green, J. J. Med. Chem. 1975, 18, 833.
14. A peak at m/z 323 (64%) in the FAB mass spectrum correlates with the M + H of the 4-nitrobenzyl carbonate resulting from reaction of the carbonylimidazole 12 with 4-nitrobenzyl alcohol used as the FAB matrix.
15. Ford, M. J.; Ley, S. V. Synlett 1990, 255.
16. March, J. Advanced Organic Chemistry, 2nd ed.; McGraw Hill: New York, 1977; p 302.
17. For a review of 1,1′-carbonyldi-1,2,4-triazole, see ref 3c, p 1010.
18. (a) Jones, C. D.; Winter, M. A.; Hirsch, K. S.; Stamm, N.; Taylor, H. M.; Holden, H. E.; Davenport, J. D.; Krumkalns, E. V.; Suhr, R. G. J. Med. Chem. 1990, 33, 416.
19. (b) Staab, H. A.; Mannschreck, A. Chem. Ber. 1962, 55, 1284.
20. Mandrou, A. M.; Potin, P.; Wylde-Lachazette, R. Bull. Soc. Chim. Fr. 1962, 1546.
21. The salts from reaction of 4 with ethereal HCl, maleic, methanesulfonic, and oxalic acids gave only oils or noncrystalline solids.