One-pot synthesis of highly regioselective β-azido alcohols catalyzed by Brønsted acidic ionic liquids
Journal: Iranian Chemical Communication (Vol.6, No. 4)Publication Date: 2018-10-01
Authors : Sarvin Mohammadi-Aghdam; Hadi Jabbari; Omidali Pouralimardan; Fater Divsar; Issa Amini; Sami Sajjadifar;
Page : 423-436
Keywords : [Cbmim]Cl; [pyridine-SO3H]Cl; epoxide; ring opening; azidoalcohols; water;
Abstract
In this protocol, 3-(2-carboxybenzoyl)-1-methyl-1H-imidazol-3-ium chloride [Cbmim]Cl and sulfonic acid functionalized pyridinium chloride [pyridine-SO3H]Cl as a new, reusable, and green Brønsted acidic ionic liquid (BAIL) catalyst were synthesized and successfully used for the one-pot ring opening of epoxide with sodium azide (NaN3) in water at room temperature. Epoxides under ring-opening easily with NaN3 in the presence of [Cbmim]Cl and [pyridine-SO3H]Cl to afford the corresponding β-azido alcohols as attractive and interesting materials in drug design and pharmaceutics compounds in high yield with good regioselective under mild reaction conditions.In this protocol, 3-(2-carboxybenzoyl)-1-methyl-1H-imidazol-3-ium chloride [Cbmim]Cl and sulfonic acid functionalized pyridinium chloride [pyridine-SO3H]Cl as a new, reusable, and green Brønsted acidic ionic liquid (BAIL) catalyst were synthesized and successfully used for the one-pot ring opening of epoxide with sodium azide (NaN3) in water at room temperature. Epoxides under ring-opening easily with NaN3 in the presence of [Cbmim]Cl and [pyridine-SO3H]Cl to afford the corresponding β-azido alcohols as attractive and interesting materials in drug design and pharmaceutics compounds in high yield with good regioselective under mild reaction conditions.
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