NIS-Promoted Chemodivergent and Diastereoselective Synthesis of Pyrrolinyl and Cyclopentenyl Spiropyrazolones via Regulated Cyclization of Alkylidene Pyrazolones with Enamino Esters

An N-iodosuccinimide-promoted annulation of alkylidene pyrazolones with enamino esters has been explored to construct a spiropyrazolone moiety through a Michael addition/iodination/intramolecular nucleophilic substitution sequence. When the reaction was performed in acetonitrile at 100 °C, it furnis...

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Published inJournal of organic chemistry Vol. 89; no. 12; pp. 9051 - 9055
Main Authors Xu, Hui, Weng, Ming-Yue, Xu, Peng, Huang, Ze-Ming, Li, Qing-Hai, Zhang, Ze
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 21.06.2024
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Summary:An N-iodosuccinimide-promoted annulation of alkylidene pyrazolones with enamino esters has been explored to construct a spiropyrazolone moiety through a Michael addition/iodination/intramolecular nucleophilic substitution sequence. When the reaction was performed in acetonitrile at 100 °C, it furnished pyrrolinyl spiropyrazolones exclusively in an anti configuration through N-attacking cyclization. When the reaction was performed in dimethyl sulfoxide at 80 °C in the presence of K2HPO4, it afforded cyclopentenyl spiropyrazolones exclusively in the syn configuration through C-attacking cyclization. A plausible mechanism has also been proposed.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c00424