کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
5217022 | 1383283 | 2014 | 5 صفحه PDF | دانلود رایگان |
A variety of N-(1-methoxyalkyl)amides react with benzotriazole in the presence of PPh3·HBF4 and organic bases (Hünig's base, DBU or DABCO) or solid-state-supported bases (SiO2-Pip or IRA-67) in CHCl3 to give N-[1-(benzotriazol-1-yl)alkyl]amides in good yields. The most convenient and efficient procedure for obtaining N-[1-(benzotriazol-1-yl)alkyl]amides consists, however, of the addition of benzotriazole sodium salt to a solution of crude 1-(N-acylamino)alkyltriphenylphosphonium salt, obtained in situ from N-(1-methoxyalkyl)amides and PPh3·HBF4. A combination of these reactions with the recently described electrochemical decarboxylative α-methoxylation of N-acyl-α-amino acids in the presence of SiO2-Pip enables an effective two-pot transformation of N-acyl-α-amino acids to N-[1-(benzotriazol-1-yl)alkyl]amides.
Journal: Tetrahedron - Volume 70, Issue 35, 2 September 2014, Pages 5725-5729