European Journal of Chemistry

Synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one from Tessmannia densiflora

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Published: Mar 28, 2011
DOI: https://doi.org/10.5155/eurjchem.2.1.117-119.201
Keywords:
Isocoumarin, Tessmannia densiflora, 3, 5-Dimethoxyhomophthalic acid, Antimalarial, 5-Dimethoxyhomophthalic anhydride, Mechanism
Section
Short Communication
Issue
Vol. 2 No. 1 (2011): March 2011
Dates
Received 2010-07-08
Accepted 2010-10-18
Published 2011-03-28


Main Article Content

Aamer Saeed
Department of Chemistry, Quaid-I-Azam University, Islamabad, PK-45320, Pakistan

Abstract

The synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one (1) isolated from the stem and root bark extracts of Tessmannia densiflora has been described. The reaction of 3,5-dimethoxyhomophthalic anhydride (2) with hexanoyl chloride in the presence of 1,1,3,3-tetramethylguanidine and triethylamine afforded 6,8-dimethoxy-3-pentylisocoumarin (3). Regioselective demethylation of the latter using anhydrous aluminum chloride furnished the title isocoumarin (1).

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Saeed, A. Synthesis of 8-Hydroxy-6-Methoxy-3-Pentyl-1H-Isochromen-1-One from Tessmannia Densiflora. Eur. J. Chem. 2011, 2, 117-119.

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Supporting Agencies

The Higher Education Commission of Pakistan (Project No. 20-Miscel/R&D/00/3834).
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