Synthesis of Spiro 3,3'-Cyclopropyl Oxindoles Via N-Bromosuccinimide-Mediated Ring-Closing and Contraction Cascade.

J Org Chem

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science and Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. China.

Published: January 2021

An N-bromosuccinimide-mediated cascade reaction involving the cyclization/oxygen-migration/ring-contraction process of 3-(β, β-diaryl) indolylethanol was disclosed. A variety of spiro 3,3'-cyclopropyl oxindole derivatives were efficiently synthesized in good yields under mild reaction conditions. A possible mechanism was suggested based on intermediate isolation and computational studies.

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http://dx.doi.org/10.1021/acs.joc.0c02610DOI Listing

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