Cesium Carbonate as an Efficient Base for Alkylation of 3-(1H-Imidazol-4-yl)pyridine

REFERENCES

• (a) Agouridas , C. ; Denis , A. ; Auger , J.-M. ; Benedetti , Y. ; Bonnefoy , A. ; Bretin , F. ; Chantot , J.-F. ; Dussarat , A. ; Fromentin , C. ; Gouin D'Ambrières , S. ; Lachaud , S. ; Laurin , P. ; Le Martret , O. ; Loyau , V. ; Tessot , N. Synthesis and antibacterial activity of ketolides (6-O-methyl-3-oxoerythromycin derivatives): A new class of antibacterials highly potent against macrolide-resistant and susceptible respiratory pathogens . J. Med. Chem. 1998 , 41 , 4080 – 4100 ; (b) Denis , A. ; Bretin , F. ; Fromentin , C. ; Bonnet , A. ; Piltan , G. ; Bonnefoy , A. ; Agouridas , C. β-Keto-ester chemistry and ketolides: Synthesis and antibacterial activity of 2-halogeno, 2-methyl, and 2,3 enol-ether ketolides . Bioorg. Med. Chem. Lett. 2000 , 10 , 2019 – 2022 .
   PubMed Web of Science ®Google Scholar
• (a) Denis , A. ; Agouridas , C. ; Auger , J. M. ; Benedetti , Y. ; Bonnefoy , A. ; Bretin , F. ; Chantot , J. F. ; Dussarat , A. ; Fromentin , C. ; D'Ambrieres , S. G. ; Lachaud , S. ; Laurin , P. ; Martret , O. L. ; Loyau , V. ; Tessot , N. ; Pejac , J. M. ; Perron , S. Synthesis and antibacterial activity of HMR 3647, a new ketolide highly potent against erythromycin-resistant and susceptible pathogens . Bioorg. Med. Chem. Lett. 1999 , 9 , 3075 – 3080 ; (b) Ripin , D. H. B. ; Vanderplas , B. C. ; Kaneko , T. ; McMillen , W. T. ; McLaughlin , R. W. (Pfizer Inc). Synthesis of macrolide antibiotic glycoside carbamate ketolides as antibacterial and antiprotozoal agents. US Patent 6,403,776, 2002 ; (c) Chu , D. ; Burger , M. ; Lin , X. ; Law , C. G. ; Plattner , J. ; Rico , A. (Chiron Corp.) Preparation of C12 modified erythromycin macrolides and ketolides having antibacterial activity. WO-Patent 2003004509 ; (d) Andreotti , D. ; Biondi , S. ; Lociuro , S. (GlaxoSmithKline Plc). Preparation of lactone ketolide macrolide erythromycin antibiotics. WO Patent 2002050092 .
   PubMed Web of Science ®Google Scholar
• Wei , H. ; Sudini , R. ; Yin , H. Regioslective synthesis of 1-alkyl-4-(3-pyridyl)-substituted imidazole . Org. Process Res. Dev. 2004 , 8 , 955 – 957 .
   Web of Science ®Google Scholar
• (a) Brown , R. S. ; Manoharan , T. S. 1-(1-Ethoxyethyl): An effective protecting group for imidazole nitrogen . J. Org. Chem. 1988 , 53 , 1107 – 1110 ; (b) Iddon , B. ; Khan , N. ; Lim , B. L. Azoles, part 4: Nucleophilic substitution reactions of halogenoimidazoles . J. Chem. Soc., Perkin Trans. 1 1987 , 1437 – 1443 ; (c) Rao , A. K. S. B. ; Rao , G. ; Singh , B. B. Regioselective alkylation of 4 (5)-Nitro-1H-imidazoles in acidic media: Study of temperature effects . J. Chem. Soc., Perkin Trans. 1 1994 , 2399 – 2402 ; (d) Ichikawa , M. ; Yamamoto , C. ; Hisano , T. Acidic properties of bezimidazoles and substituent effects, V: Protection of benzimidazoles by N-alkyl bond formation using vinylpyridines . Chem. Pharm. Bull. 1981 , 29 , 3042 – 3047 ; (e) Katritzky , A. R. ; Slawinski , J. J. ; Brunner , F. General route to 4-substituted imidazoles . J. Chem. Soc., Perkin Trans. 1 1989 , 1139 – 1145 ; (f) Iddon , B. ; Hartley , D. J. Use of the vinly group as an efficient protecting group for azole N-atoms: Synthesis of polyfuctionalized imidazoles and thieno[2,3-d] = [3,2-d]imidazole . Tetrahedron Lett. 1997 , 38 , 4647 – 4650 ; (g) Khahnadideh , S. ; Rezaei , Z. ; Khalafi-Nezhad , A. ; Bahrinajafi , R. ; Mohamadi , R. ; Farrokhroz , A. A. Synthesis of N-alkylated derivatives of imidazole as antibacterial agents . Bioorg. Med. Chem. Lett. , 2003 , 13 , 2863 – 2865 .
   Web of Science ®Google Scholar
• LaMattina , J. L. The synthesis of 2-amino-4-(4-imidazolyl) pyridines. J. Hetercycl. Chem. 1983, 20, 533–538.
   Web of Science ®Google Scholar