One-pot synthesis of highly regioselective β-azido alcohols catalyzed by Brønsted acidic ionic liquids

Authors

  • Fater Divsar Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
  • Hadi Jabbari Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
  • Issa Amini Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
  • Sami Sajjadifar Department of Chemistry, Payame Noor University, PO BOX 19395-4697 Tehran, Iran
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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Journal title

volume 6  issue Issue 4, pp. 325-460

pages  423- 436

publication date 2018-10-01

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