Access the full text.
Sign up today, get DeepDyve free for 14 days.
Loading next page...
/lp/wiley/microwave-mediated-pyrazole-fluorinations-using-selectfluor-FKpKG0lrvK
References (21)
-
Ji-Chang Xiao, J. Shreeve (2005)
Microwave-assisted rapid electrophilic fluorination of 1,3-dicarbonyl derivatives with Selectfluor®Journal of Fluorine Chemistry, 126
-
W. Ried, Gerhard Mühle (1962)
Zur Spaltbarkeit von Aryl‐ und Acyl‐hydrazonen mit AcetylacetonEuropean Journal of Organic Chemistry, 656
-
A. Guzman-Perez, R. Wester, M. Allen, J. Brown, A. Buchholz, E. Cook, W. Day, E. Hamanaka, S. Kennedy, D. Knight, P. Kowalczyk, R. Marala, C. Mularski, W. Novomisle, R. Ruggeri, W. Tracey, R. Hill (2001)
Discovery of zoniporide: a potent and selective sodium-hydrogen exchanger type 1 (NHE-1) inhibitor with high aqueous solubility.Bioorganic & medicinal chemistry letters, 11 6
-
J. Reid, M. Calvin (1950)
Some New β-Diketones Containing the Trifluoromethyl Group1aJournal of the American Chemical Society, 72
-
T. Norris, Roberto Colon-Cruz, D. Ripin (2005)
New hydroxy-pyrazoline intermediates, subtle regio-selectivity and relative reaction rate variations observed during acid catalyzed and neutral pyrazole cyclization.Organic & biomolecular chemistry, 3 10
-
A. Pace, S. Buscemi, N. Vivona (2005)
THE SYNTHESIS OF FLUORINATED HETEROAROMATIC COMPOUNDS. PART 1. FIVE-MEMBERED RINGS WITH MORE THAN TWO HETEROATOMS. A REVIEWOrganic Preparations and Procedures International, 37
-
G. Lal, G. Pez, R. Syvret (1996)
Electrophilic NF Fluorinating Agents.Chemical reviews, 96 5
-
Joseph Sloop, C. Bumgardner, W. Loehle (2002)
Synthesis of fluorinated heterocyclesJournal of Fluorine Chemistry, 118
-
M. Doyle, William Bryker (1979)
Alkyl nitrite-metal halide deamination reactions. 6. Direct synthesis of arenediazonium tetrafluoroborate salts from aromatic amines, tert-butyl nitrite, and boron trifluoride etherate in anhydrous mediaJournal of Organic Chemistry, 44
-
M. Haddadin, M. Taha, A. Jarrar, C. Issidorides (1976)
Reaction of benzofurazan oxide with unsymmetrical 1,3-diketones; steric and polar effectsTetrahedron, 32
-
Shiv Singh, Dalip Kumar, H. Batra, R. Naithani, I. Rozas, J. Elguero (2000)
The reaction between hydrazines and β-dicarbonyl compounds: proposal for a mechanismCanadian Journal of Chemistry, 78
-
M. Genin, Carolyn Biles, B. Keiser, Susan Poppe, Steven Swaney, W. Tarpley, Yoshihiko Yagi, Donna Romero (2000)
Novel 1,5-diphenylpyrazole nonnucleoside HIV-1 reverse transcriptase inhibitors with enhanced activity versus the delavirdine-resistant P236L mutant: lead identification and SAR of 3- and 4-substituted derivatives.Journal of medicinal chemistry, 43 5
-
C. Stephens, J. Blake (2004)
Nuclear fluorination of 3,5-diarylisoxazoles with Selectfluor®Journal of Fluorine Chemistry, 125
-
J. Ichikawa, Masakuni Kobayashi, Yasuharu Noda, N. Yokota, K. Amano, T. Minami (1996)
Regiocontrolled Syntheses of 3- or 5-Fluorinated Pyrazoles from 2,2-Difluorovinyl Ketones(1).The Journal of organic chemistry, 61 8
-
C. Bumgardner, Joseph Sloop (1992)
Ring-fluorinated pyrazolesJournal of Fluorine Chemistry, 56
-
O. Brady (1931)
CIII.—The use of 2 : 4-dinitrophenylhydrazine as a reagent for carbonyl compoundsJournal of The Chemical Society (resumed)
-
R. Katoch-Rouse, A. Horti (2003)
Synthesis of N‐(piperidin‐1‐yl)‐5‐(4‐methoxyphenyl)‐1‐(2‐chlorophenyl)‐4‐[18F]fluoro‐1H‐pyrazole‐3‐carboxamide by nucleophilic [18F] fluorination: a PET radiotracer for studying CB1 cannabinoid receptorsJournal of Labelled Compounds and Radiopharmaceuticals, 46
-
S. Dilli, Kevin Robard (1984)
Spectroscopic properties and gas chromatographic behaviour of aryl β-diketones and selected chelatesJournal of Chromatography A, 312
-
R. Butler, John Hanniffy, J. Stephens, L. Burke (2008)
A ceric ammonium nitrate N-dearylation of N-p-anisylazoles applied to pyrazole, triazole, tetrazole, and pentazole rings: release of parent azoles. generation of unstable pentazole, HN5/N5-, in solution.The Journal of organic chemistry, 73 4
-
R. Linderman, K. Kirollos (1989)
An efficient method for the synthesis of trifluoromethyl substituted heterocyclesTetrahedron Letters, 30
-
T. Penning, J. Talley, S. Bertenshaw, J. Carter, P. Collins, S. Docter, M. Graneto, L. Lee, James Malecha, J. Miyashiro, R. Rogers, D. Rogier, S. Yu, G. Anderson, E. Burton, J. Cogburn, S. Gregory, C. Koboldt, W. Perkins, K. Seibert, A. Veenhuizen, Yan Zhang, P. Isakson (1997)
Synthesis and biological evaluation of the 1,5-diarylpyrazole class of cyclooxygenase-2 inhibitors: identification of 4-[5-(4-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-1-yl]benze nesulfonamide (SC-58635, celecoxib).Journal of medicinal chemistry, 40 9
- Publisher
- Wiley
- Copyright
- Copyright © 2009 Wiley Subscription Services
- ISSN
- 1042-7163
- eISSN
- 1098-1071
- DOI
- 10.1002/hc.20556
- Publisher site
- See Article on Publisher Site
Abstract
Microwave‐mediated electrophilic fluorinations and a new single‐pot condensation en route to ring‐fluorinated pyrazoles were examined: The monofluorination by these methods was successful for a variety of pyrazoles, with yields ranging from 13% to 75%. While electrophilic aromatic fluorination of 3‐CF3 pyrazoles proved largely ineffective, development of a single‐pot process overcame this limitation. The microwave‐mediated reaction is regioselective; ring fluorination of the heterocycle occurs preferentially over phenyl and alkyl substituents. Alkyl side chain fluorination, when desired, can be modulated by reactant ratios. The single‐pot method, which involves acid catalysis by H‐TEDA, produces 4‐fluoropyrazoles products. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:341–345, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20556
Journal
Heteroatom Chemistry – Wiley
Published: Jan 1, 2009