O‐Alkylation of Pyridine Aldo‐ and Ketoximes with Dihalohydrins under Phase‐Transfer Conditions

Abstract

Phase‐transfer‐catalyzed alkylation of (E)‐pyridine aldo‐ and (E)‐ketoximes with dihalohydrins in the benzene (or DMSO)/10% aq. NaOH system in the presence of tetradecylammonium bromide proceeds regiospecifically to afford the corresponding O‐halohydrins in good yields. In this study, first O‐halohydrin derivatives were converted into glycidyl ether derivatives, and then a new series of amino alcohols were synthesized by the condensation of amines with these glycidyl ethers.

Keywords:

• amino alcohols
• condensation
• dihalohydrins
• epoxides
• pyridine aldo‐ and ketoximes