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

doi:10.1039/P19900000133

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 journal › Article › peer-review

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 language	English
Pages (from-to)	133-138
Number of pages	6
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	1
DOIs	https://doi.org/10.1039/P19900000133
Publication status	Published - Jan 1990
Externally published	Yes

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

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).",

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