Review of the synthesis of acyclic and cyclic oxime ethers

Abstract

Oxime ethers have attracted much attention due to their potential biological activities and wide variety of synthetic applications.

An Enantioselective CpxRh(III)‐Catalyzed C−H Functionalization/Ring‐Opening Route to Chiral Cyclopentenylamines

“…Given its relevance in biologically active compounds [16] and its versatility as afunctional group in organic synthesis, [17] we initiated our investigation with oxime ethers as the directing group using phenyl ketoxime ether 1a and diazabicycle 2a as model substrates (Table 1). We opted for ac ombination of easily accessible chiral Cp x Rh I (diene) complexes [18] and bis(benzoyl) peroxide as the activating oxidant for the generation of Cp x Rh III (OBz) 2 catalysts.B oth tested Cp x Rh I (ethylene) 2 complexes Rh1 and Rh2 provided product 3a only in low yields and moderate selectivities of 78.5:21.5 and 77:23 er (entries 1a nd 2).…”

Study of the Room‐Temperature Synthesis of Oxime Ethers by using a Super Base

“…They are used in organic synthesis, providing valuable reagentst oo btain cis-1.2-aminoalcohols, [1] hydroxyloamines, [2] enantioselectives ynthesis of the amines, [3] and,u nder specific conditions in cyclization reactions, can lead to the formation of substituted heteroaromatic compounds. [4,5] However,m any oxime ethers are applicable as specifiedc ompounds with biological activity.T hey exhibit anticancer, [6] anti-aggregation, [7] antidepressant, [8,9] anticonvulsant, [10] antimicrobial, [11] antiviral, [12] acaricidal, [13] anti-protozoal, [14] and herbicidal [15] effects. There has also been research performed on the use of oxime ethers as fragrances.…”

“…There has also been research performed on the use of oxime ethers as fragrances. [16] Oxime ethers can be obtained from the aminohydroxylation reaction of ketones [17,18] and reactions of the oximes with alcohols with triphenylphosphine, [9,19] alkenes, [9] aryl halogens, [20,21] appropriate alkyl halogens, functionalized alkyl halogens, and benzylh alogens. For the synthesis of oxime ethers in latter method,b ases in different solvents are usually used, for example CH 3 ONa in CH 3 OH, [14] NaH in DMF, [22] K 2 CO 3 in acetone/ DMF, [6] NaOH (aq) /toluene, [15] as the halogensu sed are cheap and readily available chlorides.…”

“…However, many oxime ethers are applicable as specified compounds with biological activity. They exhibit anticancer, anti‐aggregation, antidepressant, anticonvulsant, antimicrobial, antiviral, acaricidal, anti‐protozoal, and herbicidal effects. There has also been research performed on the use of oxime ethers as fragrances …”

Design, Synthesis, and Bioassay of Novel Compounds of Isolongifolenone Oxime Derivatives

“…Based on the natural products to synthesize novel compounds for application in medicine or agriculture, this study has been carried out as a result of biological and pharmacological properties of these compounds. Oxime ether derivatives, known as important precursors and intermediates for natural products and various drugs , have been the hot topic for research workers due to their bioactivity against antibacterial , antifungal , larvicidal , antiretroviral , antineoplastic , BK channel‐opening , and acaricidal activities. In addition, oxime ether derivatives have also been reported as potent anti‐inflammatory agents and inhibitors of monocyte‐to‐macrophage transformation , β ‐adrenergic blocking , anticancer agents , sugar surfactants , and ethylene inhibitor .…”