Affiliation:
1. State Key Laboratory of Antiviral Drugs Pingyuan Laboratory Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals Key Laboratory of Green Chemical Media and Reactions Ministry of Education School of Chemistry and Chemical Engineering Henan Normal University Xinxiang Henan 453007 People's Republic of China
Abstract
AbstractPresented herein is a synthesis of indane fused bicyclic pyrazolidinones based on the reactions of aryl azomethine imines with cyclopropanols. Mechanistically, the formation of product involves Rh(III)‐catalyzed direct aryl C(sp2)−H alkylation of aryl azomethine imine with cyclopropanol through in situ ring‐opening, followed by cascade intramolecular C‐ and N‐nucleophilic addition. In this tandem process, cyclopropanol acts as not only an alkylating agent but also masked nucleophile and electrophile to participate in the construction of both the indane and the bicyclic pyrazolidinone scaffolds. To our knowledge, such a cascade reaction pattern has not been disclosed. In general, this synthetic protocol has advantages such as easily obtainable substrates, valuable products, concise synthetic procedure, unique reaction pathway, and good compatibility with diverse functional groups.
Funder
National Natural Science Foundation of China
Henan Key Laboratory of Organic Functional Molecules and Drug Innovation