Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

In Situ Generated TEMPO Oxoammonium Salt Mediated Tandem Cyclization of β-Oxoamides with Amine Hydrochlorides for the Synthesis of Pyrrolin-4-ones

In Situ Generated TEMPO Oxoammonium Salt Mediated Tandem Cyclization of β-Oxoamides with Amine Hydrochlorides for the Synthesis of Pyrrolin-4-ones
Nana Ma, Tong-Xin Liu, Xuna Zhao, Guisheng Zhang
A novel in situ generated TEMPO oxoammonium salt mediated one-pot tandem reaction has been developed for the straightforward construction of pyrrolin-4-ones from readily available β-oxoamides with amine hydrochlorides. The reaction tolerates various functional groups and represents a reliable method for the synthesis of highly substituted pyrrolin-4-ones in good yields under mild conditions. Detailed mechanistic studies disclosed that TEMPO oxoammonium salt generated in situ was crucial for the transformation involving the formation of enaminone precursors in situ by condensation of the β-oxoamides with amines, followed by sequential oxidative coupling with β-oxoamides, intramolecular cyclization, and 1,2-alkyl migration steps.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00686

DOI: 10.1021/acs.joc.7b00686

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