Cyanamides and alkynamides are important intermediates in the synthesis of more elaborate structures. While these functional groups are similar in structure, they have remarkably different reactivities. We have been exploring new reactivity modes of these intermediates that allow us to create a wide array of nitrogen-containing small molecules. This research project involving undergraduate students will describe two new directions in this area: 1) transition metal-mediated intramolecular reaction methodology to make α-carbolines from cyanamides, and 2) stereoselective synthesis of functionalized imides from alkynamides. We will report a wide substrate scope for these reactions in moderate to good yield, describe our efforts to increase diastereoselectivity in imide synthesis, and demonstrate that these reactions reduce the number of steps required to synthesize more complex structures.

New reactions of cyanamides and alkynamides for the synthesis of nitrogen-containing small molecules

256th National Meeting (2018)

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