Amidine derivatives are structurally unique and possess interesting chemical properties since are found in many bioactive natural products and were found as important pharmacophores. In addition, amidines containing sulfonyl group were identified as numerous osteoclast differentiation inhibitors and antiresorptive agents. Traditionally the preparation of amidine derivatives has involved complicated function group transformations. Therefore, it is still desirable to continue the development of new methodologies, more efficient reactions, and more accessible and cheaper reagents for the preparation of these interesting compounds. To the best our knowledge, amides have not been used as starting material in one-pot procedure for the formation of amidines. During las years, our research group has developed efficient protocols for the chemoselective reduction of amides to amines, aldehydes and enamines catalyzed by Mo(CO)6. In this project, we present a novel methodology for the reduction of tertiary amides into enamines and subsequent reaction with sulfonyl azides to N-sulfonyl amidines in a one pot procedure. The amide reduction is highly effective under mild reaction conditions and the protocol tolerates sulfonyl azides with reducible groups such as nitrile, ketone, ester, and cyano, obtaining the corresponding N-sulfonyl amidines in good yields.

Synthesis of N-sulfonyl amidines through Mo(CO)6 catalyzed amide reduction to enamines

253rd National Meeting (2017)

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