Intramolecular Cyclization of Alkynylheteroaromatic Substrates Bearing a Tethered Cyano Group: A Strategy for Accessing Fused Pyridoheterocycles

Niklas Kraemer, Erin M. Eason, Thomas R. Hoye

Research output: Contribution to journalArticlepeer-review

Abstract

Heterocyclic substrates containing a conjugated alkyne and a pendant nitrile were shown to cyclize in an overall tetradehydro-Diels-Alder reaction to give products in which the initial heterocycle bears a newly fused pyridine ring. Base-promoted tautomerization of the alkyne to its isomeric allene allows this process to occur at ambient temperature. DFT studies support many of the mechanistic interpretations of the overall results.

Original languageEnglish (US)
Pages (from-to)12716-12726
Number of pages11
JournalJournal of Organic Chemistry
Volume88
Issue number17
DOIs
StatePublished - Sep 1 2023

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Publisher Copyright:
© 2023 American Chemical Society

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  • Journal Article

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