Synthesis of Azulenone Skeletons by Reaction of 2-Phenyl-2-acylketenes [RCO(Ph)C=C=O] with Alkynyl Ethers: Mechanistic Aspects and Further Transformations

Dean G. Brown, Thomas R Hoye, Ronald G. Brisbois

Research output: Contribution to journalArticlepeer-review

23 Scopus citations

Abstract

A method is described for a mild and efficient synthesis of azulenone skeletons via the addition reactions of 2-phenyl-2-acylketenes with 1-alkynyl ethers. A mechanism is presented to account for both azulenone formation as well as the solvent and substrate dependency of a competitive pyrone formation. The azulenone rings have been subsequently transformed into both substituted azulenes or hydroazulenes by derivatization and/or decarboxylation of an angular carboxyl substituent or by hydrogenation.

Original languageEnglish (US)
Pages (from-to)1630-1636
Number of pages7
JournalJournal of Organic Chemistry
Volume63
Issue number5
DOIs
StatePublished - Mar 6 1998

Fingerprint

Dive into the research topics of 'Synthesis of Azulenone Skeletons by Reaction of 2-Phenyl-2-acylketenes [RCO(Ph)C=C=O] with Alkynyl Ethers: Mechanistic Aspects and Further Transformations'. Together they form a unique fingerprint.

Cite this