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, 72 (25), 9761-4

Knorr Cyclizations and Distonic Superelectrophiles

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Knorr Cyclizations and Distonic Superelectrophiles

Kiran Kumar Solingapuram Sai et al. J Org Chem.

Abstract

The acid-catalyzed Knorr cyclization has been studied by experimental and theoretical methods. The results of these studies indicate that beta-ketoamides such as acetoacetanilide undergo diprotonation at the two carbonyl oxygen atoms to form distonic superelectrophiles. Direct observation of a dicationic superelectrophile was achieved by low-temperature 1H, 15N, and 13C NMR from FSO3H-SbF5-SO2ClF solutions. In synthetic studies, the Brønsted superacid CF3SO3H is found to be an effective acid catalyst for the Knorr cyclization.

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