Chemoselectivity is the main interest nowadays when it comes to the reduction of amides and many research groups are focusing on the development of protocols that will tolerate other reducible functional groups over the amide moiety. We recently developed an efficient and highly chemoselective protocol for the reduction of tertiary amides catalyzed by Mo(CO)6. The system was tunable by variation of the temperature which enabled for either formation of amines or aldehydes and the silane used were the environmentally friendly and inexpensive 1,1,3,3-tetramethyldisiloxane (TMDS). During the substrate scope evaluation it was observed that the phenyl acetamide was transformed into the corresponding enamine. The enamines were further used without prior isolation in a cycloaddition reaction with phenyl azides, affording the triazoline products in high yields. The triazoline products have been reported as biologically active and as anticonvulsants which makes them an interesting class of compound to synthesize. Furthermore, the reduction of the amides is chemoselective and can actually be performed with high efficiency in ethyl acetate as the solvent. The cyclization of enamines with azides have been studied before, although, to the best of our knowledge, amides have not been used as starting material in a one-pot procedure for the formation of triazolines.

Transformation of amides into highly functionalized triazolines via Mo(CO)6 catalyzed reduction

253rd National Meeting (2017)

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