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SYNTHESIS OF DIHETEROARYL SULFIDES VIA CHEMOSELECTIVE REACTION OF 4,6-DIAMINOPYRIMIDINE-2(1H)-THIONE WITH HALOHETEROARYL COMPOUNDS

Tayebeh Davodian, Reza Ranjbar-Karimi, Hossein Mehrabi
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Abstract


A series of substituted diheteroaryl sulfides was synthesized by the reaction of 4,6-diaminopyrimidine-2(1H)-thione with fluoro- and chloroheteroaromatic compounds in the presence of Na2CO3 in acetonitrile under reflux conditions. Our study indicated that 4,6-diaminopyrimidine-2(1H)-thione reacts with fluoro- and chloroheteroaromatic compounds chemoselectively as S- rather than N-nucleophile. The structures of the synthesized compounds were confirmed by IR, 1H, 19F, and 13C NMR spectroscopy, as well as elemental analysis and X-ray structural analysis.


Keywords


perhalo compounds; sulfide; aromatic nucleophilic substitution; chemoselectivity; synthesis

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