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.
p. 286 - 290
(2007/10/03)
SUBSTITUTED 1-(2-THIENYL)CYCLOHEXYLAMINES AND RELATED COMPOUNDS AS POTENTIAL NMDA ANTAGONISTS
Reactions of bisulfite addition compounds prepared in situ from cyclohexanone or 3,4,5,6-tetrahydro-2H-thiopyran-3-one with potassium cyanide and corresponding amines resulted with high yields in amino nitriles type of V and VI.These compounds were subjected to reactions with 2-thienylmagnesium bromide and in the case of the amino nitriles Vc and Vf with 5-bromo-2-thienylmagnesium bromide.Only in the case of compound Vf, a by-product X was isolated in addition to the desired 1-piperidine (VIIf).Compound VIIf was used for the synthesis of the carboxylic acid XI.The compounds prepared were tested by some methods of biochemical and behavioural pharmacology.