The Chemistry of N-Substituted Benzotriazoles; Part 11. The preparation of Tertiary Amines Containing Tertiary-Alkyl Groups from Ketones, Secondary Amines, and Organometallic Reagents
The preparation of important pharmaceutically active highly branched tertiary amines by the reaction of Grignard reagents with adducts of cyclic ketones, benzotriazole (or pyrazole) and secondary amines is far superior to previously available routes.
Katritzky, Alan R.,Najzarek, Zbigniew,Dega-Szafran, Zofia
Preparation of tertiary alkyl carbinamines, propargylamines, and α-heteroarylamines by ketone-based aminoalkylation
(Chemical Equation Presented). Ketones 6a-i were converted into their benzotriazolylamine adducts 8a-i either directly from the corresponding ketone 6a or via enamines 7b-i. Adducts 8a-i on treatment with Grignard reagents, lithium phenylacetylide, or heteroaryllithiums gave tertiary alkyl carbinamines 9a-h (47-61%), propargylamines 10a-i (30-98%), and α-heteroarylamines 11a-k (44-85%), respectively.
Katritzky, Alan R.,Yang, Hongfang,Singh, Sandeep K.