کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1315116 | 976004 | 2010 | 5 صفحه PDF | دانلود رایگان |
The regiochemistry of nucleophilic substitution of 4-phenylsulfonyl tetrafluoropyridine with unequal bidentate nucleophiles was investigated. The first nucleophilic substitution occurs at the 2-position of the pyridine ring by nitrogen nucleophile site (secondary or primary amine) followed by intermolecular ring closure at the geometrically accessible 3-position of the pyridine ring (by S, O and N nucleophiles). From this investigation, difluorinated tetrahydropyrido[3,4-b][1,4]oxazine, thiazine and pyrazine scaffolds were synthesized very readily by a one-pot annelation reaction of 4-phenylsulfonyl tetrafluoropyridine with appropriate unequal bidentate nucleophiles.
Reaction of 4-phenylsulfonyl tetrafluoropyridine with unequal bidentate nucleophiles in the presence of sodium bicarbonate and acetonitrile as solvent give difluorinated tetrahydropyrido[3,4-b][1,4]oxazine, thiazine and pyrazine systems.Figure optionsDownload as PowerPoint slide
Journal: Journal of Fluorine Chemistry - Volume 131, Issue 5, May 2010, Pages 587–591