European Journal of Chemistry 2011, 2(1), 117-119 | doi: https://doi.org/10.5155/eurjchem.2.1.117-119.201 | Get rights and content






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


Aamer Saeed (1,*)

(1) Department of Chemistry, Quaid-I-Azam University, Islamabad, PK-45320, Pakistan
(*) Corresponding Author

Received: 08 Jul 2010 | Revised: 07 Nov 2010 | Accepted: 18 Oct 2010 | Published: 28 Mar 2011 | Issue Date: March 2011

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).

2_1_117_119_800


Keywords


Isocoumarin; Tessmannia densiflora; 3,5-Dimethoxyhomophthalic acid; Antimalarial; 3,5-Dimethoxyhomophthalic anhydride; Mechanism

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DOI: 10.5155/eurjchem.2.1.117-119.201

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Funding information


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

Citations

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[1]. Hidefumi Makabe, Masaki Asai, Yasunao Hattori
Synthesis of Isocoumarin Compounds, 8-Hydroxy-6-methoxy-3-Pentyl-1H-Isochromen-1-one and Fusariumin Analog Using Palladium-Catalyzed Carbonylation Trapping with O-Enolate
HETEROCYCLES  94(8), 1542, 2017
DOI: 10.3987/COM-17-13746
/


[2]. Aisha SADDIQA, Muhammad USMAN, Osman ÇAKMAK
Isocoumarins and 3,4-dihydroisocoumarins, amazing natural products: a review
TURKISH JOURNAL OF CHEMISTRY  41, 153, 2017
DOI: 10.3906/kim-1604-66
/


[3]. Aamer Saeed
Isocoumarins, miraculous natural products blessed with diverse pharmacological activities
European Journal of Medicinal Chemistry  116, 290, 2016
DOI: 10.1016/j.ejmech.2016.03.025
/


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How to cite


Saeed, A. Eur. J. Chem. 2011, 2(1), 117-119. doi:10.5155/eurjchem.2.1.117-119.201
Saeed, A. Synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one from Tessmannia densiflora. Eur. J. Chem. 2011, 2(1), 117-119. doi:10.5155/eurjchem.2.1.117-119.201
Saeed, A. (2011). Synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one from Tessmannia densiflora. European Journal of Chemistry, 2(1), 117-119. doi:10.5155/eurjchem.2.1.117-119.201
Saeed, Aamer. "Synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one from Tessmannia densiflora." European Journal of Chemistry [Online], 2.1 (2011): 117-119. Web. 1 Oct. 2020
Saeed, Aamer. "Synthesis of 8-hydroxy-6-methoxy-3-pentyl-1H-isochromen-1-one from Tessmannia densiflora" European Journal of Chemistry [Online], Volume 2 Number 1 (28 March 2011)

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DOI Link: https://doi.org/10.5155/eurjchem.2.1.117-119.201

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