Base-induced Sommelet–Hauser rearrangement of N-(pyridinylmethyl) tetraalkylammonium salts
نویسندگان
چکیده
The base-induced Sommelet–Hauser (S–H) rearrangement of various types N -(pyridinylmethyl) tetraalkylammonium salts 2 to produce , -dialkyl-?-pyridinylamino acid esters 4 was investigated. For example, a treatment -(2-pyridinylmethyl) glycine tert -butyl ester-derived salt 2a with 1.2 equivalents potassium -butoxide in THF at ?40 °C gave the corresponding S–H product, 2-(dimethylamino)-2-(2-methylpyridin-3-yl)acetate ( 4a ), 93% yield. Our method is an efficient C–H functionalization pyridines under simple and mild conditions.
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ژورنال
عنوان ژورنال: Tetrahedron
سال: 2022
ISSN: ['0040-4020', '1464-5416']
DOI: https://doi.org/10.1016/j.tet.2022.132721