Abstract
A highly efficient synthesis of carbamatoalkyl naphthols has been performed by a one-pot three-component condensation of 2-naphthol, aldehydes, and methyl/ethyl/benzyl carbamates in the presence of cerium ammonium nitrate under solvent-free conditions at 70 oC. The solvent, optimal amounts of raw materials and catalyst, and reaction temperature are investigated. Experimental results show that only 0.1 mmol catalyst is enough to induce the conversion. Most reactions are performed within a short reaction time. The structures of all products were characterized by IR, 1H NMR, 13C NMR, MS, and elemental analysis. A mechanism to rationalize the reaction has been proposed. KEY WORDS: Carbamatoalkyl naphthols, Cerium ammonium nitrate, One-pot synthesis, Solvent-free conditions Bull. Chem. Soc. Ethiop. 2013, 27(3), 421-426.DOI: http://dx.doi.org/10.4314/bcse.v27i3.11
Highlights
Compounds bearing 1,3-amido oxygenated functional groups are ubiquitous to a variety of biologically important natural products and potent drugs including a number of nucleoside antibiotics and HIV protease inhibitors such as ritonavir, lipinavir, and the hypotensive [1]
1-carbamatoalkyl-2-naphthols can convert to 1-aminomethyl-2-naphthols by a carbamate hydrolysis reaction. 1-Aminomethyl-2-naphthols have been reported to show cardiovascular activity [2]
Though carbamatoalkyl naphthols are very important, only a few literatures focused on their synthesis have been published
Summary
Compounds bearing 1,3-amido oxygenated functional groups are ubiquitous to a variety of biologically important natural products and potent drugs including a number of nucleoside antibiotics and HIV protease inhibitors such as ritonavir, lipinavir, and the hypotensive [1]. Most of these methods suffer from drawbacks including low yields, expensive reagents and catalysts. We describe the catalytic activity of CAN for the efficient threecomponent synthesis of carbamatoalkyl naphthols (4a-r) under solvent-free conditions
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