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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

A Novel Route to the Dibenzofuran Ring System: Possible Applications as a Rigid Thyroid Hormone Template

CJ Chandler, DJ Craik and KJ Waterman

Australian Journal of Chemistry 42(8) 1407 - 1413
Published: 1989

Abstract

Photochemical cyclization reactions of iodinated diphenyl ethers to produce dibenzofuran derivatives have been studied. While U.V. irradiation of the thyroid hormone thyroxine produces a complex mixture of products, treatment of the thyroid hormone analogue 3,5-diiodo-4-(4'-methyoxphenoxy)nitrobenzene with U.V. light yielded 4-iodo-8-methoxy-2-nitrodibenzofuran (34%) in a clean reaction. The functionalized dibenzofuran framework produced in this reaction has considerable potential for the development of novel, rigid thyroid hormone analogues.

https://doi.org/10.1071/CH9891407

© CSIRO 1989

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