CFSOH-enabled cascade ring-opening/dearomatization of indole derivatives to polycyclic heterocycles.

Org Biomol Chem

College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620, China.

Published: May 2021

AI Article Synopsis

  • A novel process for producing fused polycyclic indolines involves a CF3SO3H-mediated cascade that opens β-lactams and undergoes hydroaminative cyclization.
  • This method efficiently synthesizes valuable polycyclic indoline-2-amine derivatives with yields ranging from moderate to excellent, while being tolerant to various functional groups.
  • The products can be easily transformed into related compounds such as acids, alcohols, and amides.

Article Abstract

A novel dearomatization process to produce fused polycyclic indolines via a CF3SO3H-mediated cascade ring-opening of a β-lactam and hydroaminative cyclization is demonstrated. It provides a new strategy for the synthesis of important polycyclic indoline-2-amine derivatives in moderate to excellent yields, as well as with good functional group tolerance. Moreover, transformation of the product was performed to deliver the corresponding acid, alcohol and amide smoothly.

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http://dx.doi.org/10.1039/d1ob00712bDOI Listing

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