Turkish Journal of ChemistryA Concise Synthesis and the Antibacterial Activity of 5,6-Dimethoxynaphthalene-2-carboxylic Acid
Hasan ÖZDEMİR1, Hasan SEÇEN1
1Department of Chemistry, Faculty of Arts and Sciences, Atatürk University,
2Department of Microbiology, Faculty of Medicine, Atatürk University,
Abstract: 5,6-Dimethoxynaphthalene-2-carboxylic acid was synthesized in 7 steps and with an overall yield of 46%. Bromination of 2-naphthol, and methylation with dimethyl sulfate followed by Friedel-Crafts acylation with AcCl gave 2-acetyl-5-bromo-6-methoxynaphthalene. 2-Acetyl-5-bromo-6-methoxynaphthalene was converted to 5-bromo-6- methoxynaphthalene-2-carboxylic acid by a haloform reaction. The esterification of the acid with methanol, methoxylation with NaOCH3 in the presence of CuI and subsequent de-esterification with NaOH afforded 5,6-dimethoxynaphthalene-2-carboxylic acid. The 5-bromo-6-methoxynaphthalene-2-carboxylic acid and 5,6-dimethoxynaphthalene-2-carboxylic acid were found to have in vitro antibacterial activity against some pathogenic bacteria.
Key Words: Naphthalene-2-carboxylic acids, 2-naphthol, bromination, haloform, antibacterial activity
Turk. J. Chem., 29, (2005), 199-205.
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Other articles published in the same issue: Turk. J. Chem.,vol.29,iss.2.