A. Zare, A. Moosavi‐Zare, Maria Merajoddin
Mar 1, 2012
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Journal
Journal of Molecular Liquids
Abstract
Abstract In this work, the efficiency, generality and applicability of novel Bronsted acidic ionic liquid triethylamine-bonded sulfonic acid {[Et 3 N–SO 3 H]Cl, N , N -diethyl- N -sulfoethanammonium chloride} as homogeneous and green catalyst for organic transformations under various conditions are studied. Herein, the following one-pot multi-component reactions in the presence of {[Et 3 N–SO 3 H]Cl are investigated: (i) the synthesis of β-acetamido ketones from acetophenones, aldehydes, acetonitrile and acetyl chloride in solution and under extremely mild conditions (room temperature), (ii) the preparation of 1,8-dioxo-octahydroxanthenes from dimedone (5,5-dimethyl-1,3-cyclohexanedione) (2 equiv.) and aldehydes (1 equiv.) under solvent-free conditions at moderate temperature (80 °C), and (iii) the synthesis of 14-aryl-14 H -dibenzo[ a,j ]xanthenes from β-naphthol (2 equiv.) and aldehydes (1 equiv.) in harsh conditions (120 °C) in the absence of solvent. High yields, relatively short reaction times, efficiency, generality, clean process, simple methodology, low cost, easy work-up, ease of preparation and regeneration of the catalyst and green conditions (in the synthesis of the xanthene derivatives) are advantages of the application of [Et 3 N–SO 3 H]Cl as catalyst in the above organic reactions. This work is the first report of the ionic liquid.