Title of article :
Synthesis of 3-cyano-2-fluoropyridines
Author/Authors :
Shestopalov، نويسنده , , Anatoliy M. and Rodinovskaya، نويسنده , , Ludmila A. and Fedorov، نويسنده , , Alexander E. and Kalugin، نويسنده , , Victor E. and Nikishin، نويسنده , , Kirill G. and Shestopalov، نويسنده , , Alexandr A. and Gakh، نويسنده , , Andrei A.، نويسنده ,
Issue Information :
روزنامه با شماره پیاپی سال 2009
Abstract :
The synthesis of 3-cyano-2-fluoropyridines from readily available precursors was achieved via nucleophilic substitution of a leaving group in the 2-postion with KF or Bu4NF in polar aprotic solvents such as DMF and DMSO. Ionic tetrahydrothiophenium fragment is the most effective leaving group, the methanesulfonyl moiety is a somewhat less effective, and Br- and Cl- are the least effective. Relatively mild conditions of the reaction between (2-pyridyl)-tetrahydrothiophenium salts and KF, as well as the convenience of one-step synthesis of these salts from 2(1H)-pyridinethiones, make these salts the compounds of choice for the preparation of ring-fluorinated pyridines.
Keywords :
Fluoropyridines , Synthesis , nucleophilic substitution
Journal title :
Journal of Fluorine Chemistry
Journal title :
Journal of Fluorine Chemistry