A new synthesis of anthraquinones using dihydro-oxazoles and Grignard reagents derived from Mg(Anthracene)(THF)31

Teresa M. Nicoletti, Colin L. Raston, Melvyn V. Sargent

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

A general synthesis of anthraquinones which depends on the displacement of the methoxy group from an o-methoxyaryldihydro-oxazole by a methoxy substituted benzylmagnesium chloride, generated by using a magnesium-anthracene complex, has been developed. The masked benzyl-benzoic acids which result from these reactions are deprotected and then ring-closed to anthrones which on oxidation yield anthraquinones. In this way, the following naturally occurring anthraquinones (or derivatives thereof have been synthesized): chrysophanol (9), islandicin (19), digitopurpone (21), tri-O-methylemodin (26), and di-O-methylsoranjidiol (29).

Original languageEnglish
Pages (from-to)133-138
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number1
DOIs
Publication statusPublished - Jan 1990
Externally publishedYes

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