General synthesis of 1-substituted 2-methylbenzimidazoles from ketones and 2-aminoacetanilide

Synthetic Communications

Volumn 37, Issue 18, 2007, Pages 3029-3039

  Burova, Svetlana A ^a   Davis, Roman ^a   Fitzgerald, Russ N ^a   Johnson, Byron S ^a   Matsuoka, Richard T ^a  

^a GLAXOSMITHKLINE   (United States)

Author keywords

Benzimidazoles; Cyclization; Reductive amination

Indexed keywords

1,2 METHYLBENZIMIDAZOLE DERIVATIVE; 2 AMINOACETANILIDE; ACETANILIDE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CYCLIZATION; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROSPRAY; MASS SPECTROMETRY;

EID: 34548596627     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701542996     Document Type: Article

References (22)

1. (a) Examples of benzimidazoles in active pharmaceutical ingredients include antisecretory omeprazole (Prilosec), antihypertensive telmisartan (Micardis), and anthelminthic albendazole (Zentel);
2. (b) Nishiyama, Y.; Fujimoto, M.; Sonoda, N. Synlett 2006, 109, and references cited therein;
3. (c) Preston, P. N. The Chemistry of Heterocyclic Compounds: Benzimidazoles and Congeneric Tricyclic Compounds; John Wiley & Sons: New York, vol. 40, 1980.
4. (a) Yang, D.; Fokas, D.; Li, J.; Yu, L.; Baldino, C. M. Synthesis 2005, 1, 47;
5. (b) Rueckle, T.; Biamonte, M.; Grippi-Valloton, T.; Arkinstall, S.; Cambet, Y.; Camps, M.; Chabert, C.; Church, D. J.; Halazy, S.; Jiang, X.; Martinous, I.; Nichols, A.; Sauer, W.; Gotteland, J.-P. J. Med. Chem. 2004, 47, 6921;
6. (c) Wu, Z.; Rea, P.; Wickahm, G. Tetrahedron Lett. 2000, 41, 9871;
7. (d) Thomas, A. P.; Allott, C. P.; Gibson, K. H.; Major, J. S.; Masek, B. B.; Oldham, A. A.; Ratcliffe, A. H.; Roberts, D. A.; Russell, S. T.; Thomason, D. A. J. Med. Chem. 1992, 35, 377.
8. (a) Lin, S.-Y.; Isome, Y.; Stewart, E.; Liu, J.-F.; Yohannes, D. Tetrahedron Lett. 2006, 47, 2883, and references cited therein;
9. (b) Wright, J. B. Chem. Rev. 1951, 48, 397;
10. (c) Preston, P. N. Chem. Rev. 1974, 74, 279;
11. (d) Gray, D. N. J. Heterocycl. Chem. 1970, 7, 947;
12. (e) Hudkins, R. L. Heterocycles 1995, 41, 1045;
13. (f ) Brain, C. T.; Brunton, S. A. Tetrahedron Lett. 2002, 43, 1893;
14. (g) Brain, C. T.; Steer, J. T. J. Org. Chem. 2003, 68, 6814;
15. (h) Howarth, J.; Hanlon, K. Tetrahedron Lett. 2001, 42, 751;
16. (i) Hendrickson, J. B.; Hussoin, S. M. J. Org. Chem. 1989, 54, 1144.
17. Salehi, P.; Dabiri, M.; Zolfigol, M.; Otokesh, S.; Baghbanzadeh, M. Tetrahedron Lett. 2006, 47, 2557.
18. DiCesare, J. C.; White, C. E.; Rasmussen, W. E.; White, B. M.; McComas, C. B.; Craft, L. E. Synth. Commun. 2005, 35, 663.
19. McLaughlin, M.; Palucki, M.; Davies, I. W. Org. Lett. 2006, 8, 3307.
20. Abdel-Magid, A. F.; Carson, K. G.; Harris, B. D.; Maryanoff, C. A.; Shah, R. D. J. Org. Chem. 1996, 61, 3849.
21. Paul, S. F. US Patent 5,697,987, December 16, 1997.
22. Fitzpatrick, S. W. US Patent 4,897,497, January 30, 1990. Methyl tetrahydrofuran can be derived from cellulosic materials, including agricultural waste, coffee grounds, leaves, and sawdust, and can be blended with ethanol and alkanes to make homegrown transportation fuels. The MTHF-alkane mother liquors (filtrates and wash) are presumably suitable for direct recycling as transportation fuels.