Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

8-fluoropurine compounds

Patent ·
OSTI ID:873863

An efficient, regiocontrolled approach to the synthesis of 8-fluoropurines by direct fluorination of purines with dilute elemental fluorine, or acetyl hypofluorite, is provided. In a preferred embodiment, a purine compound is dissolved in a polar solvent and reacted with a dilute mixture of F.sub.2 in He or other inert gas.

Research Organization:
University of California
DOE Contract Number:
FC03-87ER60615
Assignee:
Regents of Univ. of California (Oakland, CA)
Patent Number(s):
US 6262254
OSTI ID:
873863
Country of Publication:
United States
Language:
English

References (46)

Activating unreactive sites of organic molecules using elemental fluorine journal June 1987
Synthesis and biological evaluations of certain 2-halo-2'-substituted derivatives of 9-.beta.-D-arabinofuranosyladenine journal February 1988
Regioselective Fluorination of Substituted Guanines with Dilute F 2 :  A Facile Entry to 8-Fluoroguanine Derivatives journal January 1996
Fluorinated Substrate Analogs: Routes of Metabolism and Selective Toxicity book January 1983
Introduction of Fluorine Into the C8 Position of Purine Nucleosides journal February 1990
Nucleic acid related compounds. III. Facile synthesis of 5-fluorouracil bases and nucleosides by direct fluorination journal October 1971
Comparison of theoretical and experimental approaches to determination of conformation of nucleosides about the glycosidic bond journal November 1980
Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV journal March 1990
Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds journal October 1983
Nucleic acid related compounds. 47. Synthesis and biological activities of pyrimidine and purine "acyclic" nucleoside analogs journal November 1984
The Formation of the CF Bond: The Last Twelve Years book September 1995
Functionalization of Organic Molecules by Xenon Fluorides book September 1995
Elemental Fluorine to 8-Fluoropurines in One Step journal January 1996
Synthesis of 6-[18F] and 4-[18F]fluoro-l-m-tyrosines via regioselective radiofluorodestannylation journal March 1993
Substrate selectivity and orientation in aromatic Substitution by molecular fluorine journal May 1980
Studies of Nucleosides and Nucleotides. XLIX. Synthesis of 8-Fluoroadenosine journal January 1971
The Direct Conversion of Chloropurines to Fluoropurines 1 journal September 1963
Site-selective fluorination of organic compounds using 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts (selectfluor reagents) journal May 1993
A General Approach to Organic Reactivity: The Configuration Mixing Model book January 1985
Methods of Fluorination in Organic Chemistry journal August 1981
Studies of nucleosides and nucleotides. journal February 1974
Power- and structure-variable fluorinating agents. The N-fluoropyridinium salt system journal November 1990
Tetrahedron report number 221 journal January 1987
Preparation of some 2'-deoxy-5-fluorouridine derivatives by a direct fluorination journal January 1976
Novel route to 3(5)-fluoro-1,2,4-triazoles and 8-fluoropurines by displacement of the nitro group journal December 1973
Regioselective radiofluorodestannylation with [18F]F2 and [18F]CH3COOF: A high yield synthesis of 6-[18F]fluoro-l-dopa
  • Namavari, Mohammad; Bishop, Allyson; Satyamurthy, N.
  • International Journal of Radiation Applications and Instrumentation. Part A. Applied Radiation and Isotopes, Vol. 43, Issue 8 https://doi.org/10.1016/0883-2889(92)90217-3
journal August 1992
Functionalisation including fluorination of caffeine, guanosine tetraacetate, and uridine triacetate using electrochemical oxidation journal December 1994
Functionalization Including Fluorination of Nitrogen-Containing Compounds Using Electrochemical Oxidation. journal January 1996
Activation of tertiary paraffins by elemental fluorine journal January 1984
Synthesis of 2′,3′,5′-tris-O-acetyl-8-fluoroadenosine journal January 1976
2-Fluoroformycin and 2-aminoformycin. Synthesis and biological activity journal November 1985
Nucleic acid related compounds. 21. Direct fluorination of uracil and cytosine bases and nucleosides using trifluoromethyl hypofluorite. Mechanism, stereochemistry, and synthetic applications journal October 1976
A direct method for the preparation of 2-hydroxyethoxymethyl derivatives of guanine, adenine, and cytosine journal May 1980
Regiospecific aromatic fluorodemetallation of group IVb metalloarenes using elemental fluorine or acetyl hypofluorite journal June 1987
Direct liquid phase fluorination of aromatic compounds journal March 1970
Application of elemental fluorine in organic synthesis journal December 1986
Elemental fluorine as a legitimate reagent for selective fluorination of organic compounds journal August 1988
Controlled, regiospecific oxidation of pyridine carboxylic acids and esters with elemental fluorine journal January 1988
Electrophilic and nucleophilic approaches to the synthesis of 3-fluorodiazepam journal June 1987
Substitutions and Additions in the Heterocyclic Rings of Nucleic Acid Bases and their Derivatives book January 1972
A direct synthesis of 5-fluorocytosine and its nucleosides using trifluoromethyl hypofluorite journal January 1972
Bimanes. 21. syn-(Methyl fluoro)bimane formation via acetyl hypofluorite journal October 1985
Quantum Chemical Study of the Electronic and Conformational Characteristics of Adenosine and 8-Substituted Derivatives: Functional Implications in the Mechanism of Reaction of Adenosine Deaminase journal February 1990
Remote and selective electrophilic fluorinations at the carbon-hydrogen single bond journal October 1980
Nucleic acid related compounds. 34. Non-aqueous diazotization with tert -butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleosides journal September 1981
Synthesis and biochemical properties of 8-amino-6-fluoro-9-.beta.-D-ribofuranosyl-9H-purine journal October 1986