Inspired by the heterocyclic structure of an active pharmaceutical compound, a nickel catalyzed synthesis of quinazolinediones was explored and developed. Iterative rounds of catalyst screening resulted in the discovery of conditions that allowed for reaction of a broad range of isocyanates with isatoic anhydrides to form <i>N</i>-alkyl and <i>N</i>-aryl quinazolinediones as well as constitutionally isomeric benzoxazinone imines. Good levels of selectivity have been demonstrated when using chiral ligands for the formation atropisomeric quinazolinediones. The structure of the isocyanate has a major impact on reactivity and selectivity. Substrate control in this reaction is rationalized through mechanistic studies.

Nickel catalyzed synthesis of quinazolinediones and benzoxazinone imines

256th National Meeting (2018)

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