Imidazol-1-yl-acetic Acid as a Green Simple Bifunctional Organocatalyst for the Regioselective Conversion of Epoxides to 1,2-azido Alcohols and β-hydroxythiocyanates
Simin Nazari, Nasir Iravani, Amanollah Zarei Ahmady, Masoumeh Vafaee-nezhad and Mosadegh Keshavarz
Affiliation: Department of Chemistry, Sousangerd Branch, Islamic Azad University, Sousangerd 44181-6189, Iran and Department of Gas and Petroleum, Yasouj University, P.O. Box 353, Yasouj, 75918-74831 Iran.
Imidazol-1-yl-acetic acid is introduced as a new, efficient and recyclable green bifunctional organocatalyst for
the synthesis of β-hydroxythiocyanate and 1,2-azido alcohols under mild conditions. This catalyst can be recovered by
simple filtration and recycled up to 8 consecutive runs without losing any of its efficiency. Various advantages associated
with this protocol include simple workup procedure, short reaction times, high product yields, greater regioselectivity.
Keywords: Imidazol-1-yl-acetic acid, epoxide, ring opening, bifunctional organocatalyst, sodium azide, sodium thiocyanate.
green chemistry, nucleophile, electrophile, regioselective.
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