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Dimethyl Sulfoxide and N-Iodosuccinimide Promoted 5-exo-dig Oxidative Cyclization of Yne-Tethered Ynamide: Access to Pyrrolidones and Spiro-pyrrolidones

B. Prabagar, Sanatan Nayak, Rangu Prasad and Akhila K. Sahoo*

*School of Chemistry, University of Hyderabad, Hyderabad 500046, India, Email: aksscuohyd.ac.in

B. Prabagar, S. Nayak, R. Prasad, A. K. Sahoo, Org. Lett., 2016, 18, 3066-3069.

DOI: 10.1021/acs.orglett.6b01149 (free Supporting Information)


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Abstract

Dimethyl sulfoxide (DMSO) and N-iodosuccinimide mediate a metal-free regioselective 5-exo-dig oxidative cyclization of propargyl-substituted ynamides via in situ generated enol equivalents. The reaction allows easy access to functionalized pyrrolidone skeletons. The role of DMSO as oxidant in the transformation is clarified, and a tentative reaction pathway is proposed.

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Key Words

3-pyrrolin-2-ones, DMSO, NIS


ID: J54-Y2016