Synthesis of Azocane-and Oxocane-Annulated Furans by a [2+2]Â Photocycloaddition-Ring-Opening Cascade

Xinyao Li, Christian Jandl, Thorsten Bach

Research output: Contribution to journalReview articlepeer-review

5 Scopus citations

Abstract

The title compounds were synthesized from readily available quinolone and coumarin derivatives by a cascade reaction (12 examples, 90-98% yield). The cascade comprised a [2+2] photocycloaddition which occurred upon sensitized irradiation at λ = 420 nm (or direct UV irradiation at λ = 366 nm) and a subsequent acid-catalyzed ring-opening reaction. A variety of substituents are compatible with the conditions and a 3-Alkyl group in the coumarin (or quinolone) is crucial to achieve a high chemoselectivity. Key to the success of the ring opening is the formation of a 4,5,5a-Trihydrocyclobuta-2 H-furan containing a strained bridgehead double bond which stems from the allenyl group tethered to the 4-position of the starting materials.

Original languageEnglish
Pages (from-to)723-730
Number of pages8
JournalSynthesis
Volume53
Issue number4
DOIs
StatePublished - 16 Feb 2021

Keywords

  • azocane
  • cycloaddition
  • domino reaction
  • heterocycles
  • oxocane
  • photochemistry
  • ring expansion

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