A Convenient Synthesis of Psoralen Derivatives Oxygenated in the Pyrone Ring: 4-Methoxypsoralen and 3,4-Dimethoxypsoralen (Halkendin)

descriptionPublicationkeyboard_double_arrow_right Article 01 Jun 1979 English Publisher:CSIRO PublishingJournal:Australian Journal of Chemistry, volume 32, pages 1,361-1,367 (issn: 0004-9425, eissn: 1445-0038,

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Authors: VK Ahluwalia; C Prakash; RP Singh;

doi: 10.1071/ch9791361

A Convenient Synthesis of Psoralen Derivatives Oxygenated in the Pyrone Ring: 4-Methoxypsoralen and 3,4-Dimethoxypsoralen (Halkendin)

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Abstract

A convenient synthesis of psoralen derivatives oxygenated in the pyrone ring, viz. 5-methoxy-7 H -furo[3,2-g][l]benzopyran-7-one (4-methoxypsoralen) and 5,6-dimethoxy-7 H -furo[3,2-g][l]benzopyran-7-one (3,4-dimethoxypsoralen or halkendin), has been achieved by blocking the 8-position of the coumarin ring with an iodo group, Claisen migration, and subsequent cyclization.

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