Trapping of Hexadehydro-Diels-Alder Benzynes with Exocyclic, Conjugated Enals as a Route to Fused Spirocyclic Benzopyran Motifs

Tao Wang, Christian J. Oswood, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

Exocyclic, conjugated enals react with benzynes generated by heating various triyne-containing substrates to produce spirocyclic benzopyran derivatives. These products are consistent with a mechanistic sequence that involves initial net [2+2] cycloaddition of the benzyne and aldehyde followed by 4π-electrocyclic ring opening and 6π ring closing.

Original languageEnglish (US)
Pages (from-to)2933-2935
Number of pages3
JournalSynlett
Volume28
Issue number20
DOIs
StatePublished - Dec 18 2017

Bibliographical note

Publisher Copyright:
© Georg Thieme Verlag Stuttgart. New York.

Keywords

  • arynes
  • benzoxetenes
  • cascades
  • electrocyclizations
  • spirocycles

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