Process for producing 8-fluoropurines

作者: Nagichettiar Satyamurthy , Michael E. Phelps , Jorge R. Barrio , Mohammad Namavari

DOI:

关键词: Purine metabolismAcetyl hypofluoriteInertSolventOrganic chemistryInert gasFluorineScientific methodChemistry

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

参考文章(33)
Addy Pross, A General Approach to Organic Reactivity: The Configuration Mixing Model Advances in Physical Organic Chemistry. ,vol. 21, pp. 99- 196 ,(1985) , 10.1016/S0065-3160(08)60099-4
Christopher Walsh, Fluorinated Substrate Analogs: Routes of Metabolism and Selective Toxicity Advances in Enzymology - and Related Areas of Molecular Biology. ,vol. 55, pp. 197- 289 ,(1983) , 10.1002/9780470123010.CH3
Jorge R. Barrio, Mohammad Namavari, Michael E. Phelps, Nagichettiar Satyamurthy, Regioselective Fluorination of Substituted Guanines with Dilute F2: A Facile Entry to 8-Fluoroguanine Derivatives Journal of Organic Chemistry. ,vol. 61, pp. 6084- 6085 ,(1996) , 10.1021/JO960761D
Morris J. Robins, S. R. Naik, Nucleic acid related compounds. III. Facile synthesis of 5-fluorouracil bases and nucleosides by direct fluorination Journal of the American Chemical Society. ,vol. 93, pp. 5277- 5278 ,(1971) , 10.1021/JA00749A063
A. Luxen, J.R. Barrio, N. Satyamurthy, G.T. Bida, M.E. Phelps, Electrophilic and nucleophilic approaches to the synthesis of 3-fluorodiazepam Journal of Fluorine Chemistry. ,vol. 36, pp. 83- 92 ,(1987) , 10.1016/S0022-1139(00)82056-4
Ryszard Stolarski, Andrzej Pohorille, Lech Dudycz, David Shugar, Comparison of theoretical and experimental approaches to determination of conformation of nucleosides about the glycosidic bond Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis. ,vol. 610, pp. 1- 19 ,(1980) , 10.1016/0005-2787(80)90051-9
Victor E. Marquez, Christopher K. H. Tseng, Hiroaki Mitsuya, Shizuko Aoki, James A. Kelley, Harry Ford, Jeri S. Roth, Samuel Broder, David G. Johns, John S. Driscoll, Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV. Journal of Medicinal Chemistry. ,vol. 33, pp. 978- 985 ,(1990) , 10.1021/JM00165A015