A new copper catalysed intramolecular C-H amination of C(sp3)-H bond adjacent to N-atom has been developed for the synthesis of quinazolin-4(3H)-one derivatives from commercially available isatoic anhydride with primary and secondary amines. This protocol involves an unusual and unexpected cleavage of N-C bond afforded the quinazolin-4(3H)-one derivatives along with quinazolin-4(1H)-one derivatives, while using N-methylisatoic anhydride. The synthetic utility of this strategy was illustrated by the convenient synthesis of rutaecarpine via Ring-Opening Cyclization (ROC) of isatoic anhydride by tryptoline under the same reaction conditions.

Copper-catalyzed intramolecular C-H amination for the synthesis of quinazolinone derivatives and rutaecarpine via ring-opening cyclization (ROC) strategy

254th National Meeting (2017)

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