Oxime ethers as versatile precursors in organic synthesis: a review

Abstract

This review is a survey of the literature describing synthetic applications of oxime ethers. The cyclization and metal-catalyzed cross-coupling reactions of oxime ethers in recent years are also highlighted.

Photosensitized Intermolecular Carboimination of Alkenes through the Persistent Radical Effect

“…Unlike carboamination reactions, the carboimination of alkenes is still in its infancy and is mainly limited to intramolecular annulation reactions generating five‐ or six‐membered N‐heterocycles . Additionally, the high reactivity of iminyl radicals has been utilized in a plethora of 1,5‐hydrogen atom transfer (HAT) reactions . In all of these cases, iminyl radicals are first generated from oxime esters through a single electron transfer (SET) event (Figure B, left) .…”

“…[17] Additionally,the high reactivity of iminyl radicals has been utilized in ap lethora of 1,5hydrogen atom transfer (HAT) reactions. [18,19] In all of these cases,i minyl radicals are first generated from oxime esters through as ingle electron transfer (SET) event ( Figure 1B, left). [19] Alternatively,o xime esters have also been employed successfully in the photosensitized generation of iminyl radicals through NÀOb ond homolysis.…”

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

“…Oxime ethers are compounds that are becoming increasingly popular. They are used in organic synthesis, providing valuable reagents to obtain cis ‐1.2‐aminoalcohols, hydroxyloamines, enantioselective synthesis of the amines, and, under specific conditions in cyclization reactions, can lead to the formation of substituted heteroaromatic compounds . However, many oxime ethers are applicable as specified compounds with biological activity.…”

“…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.…”

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 .…”