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Programmed Sequential Additions to Halogenated Mucononitriles

preprint
submitted on 04.09.2020 and posted on 07.09.2020 by Adam Zahara, Elsa Hinds, Andrew Nguyen, Sidney Wilkerson-Hill
Dihalomucononitriles were synthesized and their reactivity evaluated to assess their ability to function as linchpin reagents. Bis(2-chloroacrylonitrile) and bis(2-bromoacrylonitrile) were synthesized from 2,13-benzothiadiazole and shown to undergo conjugate addition reactions with both nitrogen (40–95% yield) and carbon nucleophiles (72–93% yield). Secondary amines were found to undergo monoadditions while carbon nucleophiles added twice. The sequence of addition of the nucleophiles could be controlled giving mixed addition products. The multicomponent coupling products could then be converted to natural product-like motifs using intramolecular cyclization reactions.

History

Email Address of Submitting Author

smwhill@email.unc.edu

Institution

The University of North Carolina at Chapel Hill

Country

United States

ORCID For Submitting Author

0000-0002-4396-5596

Declaration of Conflict of Interest

The authors declare no competing financial interest.

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