Synthetic elaboration of N-substituents in thioamides

Article abstract of DOI:10.1016/0040-4020(95)00483-O

N-(Benzotriazol-1-ylmethyl)arylthioamides, readily prepared from arylthioamides, formaldehyde and benzotriazole, undergo lithiation followed by reactions with alkyl halides, aldehydes and ketones to introduce the expected N-substituents into the N-methylene group. Subsequent displacements of the benzotriazolyl group by Grignard reagents, alkoxide or thioalkoxide anions provide general access to a wide variety of N-substituted thioamides in good yields.