Rice scientists simplify the incorporation of nitrogen into molecules

Rice University News & Media

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David Ruth713-348-6327david@rice.edu
Mike Williams713-348-6728mikewilliams@rice.edu

Rice University lab’s reagents ease chemical design for drugs, agriculture
HOUSTON – (July 12, 2017) – A Rice University laboratory that specializes in synthesizing reagents and intermediate molecules for the design and manufacture of drugs and other fine chemicals has delivered on a promise to generalize the synthesis of electrophilic (electron-poor) aminating agents.
Aminating agents are valuable building blocks that can incorporate nitrogen atoms into molecules in a single efficient step without the use of contaminating metals or catalysts.
Rice researchers, from left, László Kürti, Surached Siriwongsup and Padmanabha Kattamuri stand by the custom reactor they use to produce a nitrogen polarity-reversal agent in bulk. The aminating agents derived from it are meant to simplify the process by which chemists design drugs and other compounds. Photo by Jeff Fitlow
In his lab, Rice synthetic organic chemist László Kürti showed a tray piled high with the new reactivity-modifying agent, a nitrogen umpolung reagent used to synthesize aminating agents. An umpolung reverses the polarity of nitrogen atoms, which allows them to react differently with other atoms.
Kürti expects the robust umpolung reagent will give chemists easy access to highly sought-after, electron-poor nitrogen atoms when condensed with virtually any electron-rich primary amine.
The process is the subject of a paper in the Journal of the American Chemical Society.
When the design of a new drug involves trial and error and each trial may take hundreds of chemical steps over days and weeks, any effort to simplify existing synthetic routes is worthwhile, Kürti said. “This novel approach represents an operationally simple, scalable and environmentally friendly alternative to transition metal-catalyzed, carbon-nitrogen cross-coupling methods that are currently used to access structurally diverse amines,” he said.
Padmanabha Kattamuri holds a ...

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