Reactions of 4-substituted tetrafluoropyridine derivatives with sulfur nucleophiles: SNAr and annelation processes

Reactions of model sulfur centred nucleophiles with 4-nitro-, 4-phenylsulfonyl- and 4-cyano-tetrafluoropyridine gave products arising from substitution of the nitro- and sulfonyl substituent or ring fluorine respectively. Ring fused products are formed upon reaction of 4-cyano-tetrafluoropyridine with mercapto-acetic acid ethyl ester.

Graphical abstractReactions of sulfur centred nucleophiles with tetrafluoropyridine derivatives gave substitution or ring-fused products arising from displacement of the 4-substituent or ring fluorine.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► 4-Tetrafluoropyridine derivatives react with sulfur nucleophiles. ► Ipso substitution of 4-nitro and 4-phenylsulfonyl substituents occur. ► Thieno[2,3-c]pyridine products formed from 4-cyano-tetrafluoropyridine.