Natural products containing nitrogen-nitrogen (N-N) bonds have been shown to have promising biological activity but are uncommon in nature. This presents the opportunity to effectively synthesize compounds containing N-N bonds in the lab. The current method of synthesis is to add functionality to a protected hydrazine, which can be dangerous, due to hydrazine’s extreme reactivity. This is also inefficient, due to the number of linear steps required to fully derivatize the hydrazine. This research proposes a new method of synthesis using a compound with a chlorinated nitrogen reacting with another compound with a deprotonated nucleophilic nitrogen in an reaction to directly form the N-N bond. This method is convergent, allowing for fewer linear steps, theoretically increasing overall yield. In addition, this method is safer due to the omission of hydrazine.

Novel method of formation of substituted nitrogen-nitrogen bonds

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