Fe-Catalyzed Domino Intramolecular Nucleophilic Substitution of 4-Hydroxychromen-2-one and Pyran-2-one/Ring Opening of Activated Arene: An Easy Access to 2,3-Disubstituted Furo[3,2,-c]coumarins and Furo[3,2,-c]pyran-4-ones via Nonsymmetric Triarylmethanes

Wayland E. Noland, Honnaiah Vijay Kumar, Arjun Sharma, Binyuan Wei, Selamawit Girmachew

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

A one-pot synthesis of functionalized 2,3-disubstituted furo[3,2,-c]coumarins and furo[3,2,-c]pyran-4-ones under hydrated ferric sulfate catalysis was performed. It was revealed that the reaction proceeds with intramolecular cyclofunctionalization of nonsymmetric triarylmethanes via ring opening of 2-methylfuran followed by recyclization, resulting in the selective formation of desired products. The versatility of this method was demonstrated via the succinct synthesis of an anticoagulant agent analogue and 2,3-disubstituted benzofurans.

Original languageEnglish (US)
Pages (from-to)1801-1806
Number of pages6
JournalOrganic Letters
Volume22
Issue number5
DOIs
StatePublished - Mar 6 2020

Bibliographical note

Funding Information:
The authors thank Victor G. Young Jr., Ph.D. (X-ray Crystallographic Laboratory, University of Minnesota), for assistance with the crystal structure, and the Wayland E. Noland Research Fellowship Fund at the University of Minnesota Foundation for generous financial support of this project.

Publisher Copyright:
Copyright © 2020 American Chemical Society.

Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.

PubMed: MeSH publication types

  • Journal Article
  • Research Support, Non-U.S. Gov't

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