کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5224114 | 1383507 | 2010 | 9 صفحه PDF | دانلود رایگان |
Suzuki-Miyaura cross-coupling processes on N-pyridinium bromoazinyl aminides allow access to 3,5-disubstituted N-alkyl-2-aminopyridines. The synthetic pathway involves a regioselective bromination of pyridinium N-(pyridin-2-yl)aminide and a subsequent reaction with boronic acids to afford monosubstituted aminides in good yields. An additional bromination in the 5-position of the pyridine ring followed by a coupling reaction gives pyridinium N-(3,5-diarylpyridin-2-yl)aminides. Finally, a regioselective alkylation on the exo-nitrogen and reduction of the N-N bond yields highly substituted 2-aminopyridines.
The N-(pyridin-2-yl)pyridinium aminide allows, through two regioselective brominations followed by Suzuki-Miyaura cross-coupling processes together with a selective alkylation on the exo-nitrogen and reduction of the N-N bond, the access to 3,5-disubstituted N-alkyl-2-aminopyridines.
Journal: Tetrahedron - Volume 66, Issue 14, 3 April 2010, Pages 2624-2632