A Convenient Practical Synthesis of Alkyl and Aryl Oxime Esters

Abstract

A facile access to the synthesis of alkyl and aryl oxime esters of ketoximes and aldoximes in high yields (90-97%) is reported. The reactions were performed using N- [3-(methylamino)propyl]-N′-ethylcarbodiimide hydrochloride (EDCI) reagent in the presence of 4-(dimethylamino)pyridine (DMAP) as a catalyst at room temperature. The isolation and purification of products is very simple and in cases where product is solid, column chromatography is avoided.

Betulonic and Platanic Acids as a Basis for the Synthesis of New Therapeutically Effective Substances

“…Kromě dalších možností můžeme oximy dále modifikovat působením acylačních a alkylačních činidel na oximestery nebo oximethery. Jedním ze způsobů přípravy oximesterů je syntéza acylhalogenidů kyselin s oximy za běžných podmínek nebo reakce anhydridů kyselin s oximy v přítomnosti silné kyseliny [21][22][23] . Dalším způsobem je přímá esterifikace mezi karboxylovou kyselinou a alkoholem s využitím karbodiimidových činidel (např.…”

“…Dalším způsobem je přímá esterifikace mezi karboxylovou kyselinou a alkoholem s využitím karbodiimidových činidel (např. EDCI) v přítomnosti DMAP v DCM za pokojové teploty, vedoucí k vysokým výtěžkům v optimálním čase 21,24 . V případě syntézy oximetherových derivátu je realizována nejčastěji reakce oximů s alkyl/arylhalogenidy, nejčastěji chloridy případně bromidy.…”

Ring-Opening of Donor-Acceptor Cyclopropane Diester for the Synthesis of Oxime Esters and 2,3-Dihydroazete Ester

“…The synthesis of oxime esters by one of the most straightforward methods, which involves the treatment of alkyl- or aryl-substituted oximes with aliphatic or aromatic acids in the presence of N -[3-(methylamino)propyl]- N ′-ethyl carbodiimide hydrochloride (EDCI) reagent is shown in Scheme 1 A. 14 Furthermore, traditional methods often require a similar carbonyl ester substrate and an amine group to synthesize target oxime esters (Scheme 1 B, left). 15 In contrast, we have developed an approach for the construction of oxime esters by using strained ring systems as one of the precursors along with hydroxylamine derivatives (Scheme 1 B, right).…”

Oxime derivatives of betulonic acid and platanic acid as novel cytotoxic or antiviral agents

“…36 To synthesize other target oxime ester derivatives of 1, i.e., compounds 9-13, oxime 5 was reacted with the appropriate carboxylic acids, using either T3P in pyridine as the condensation reagent (to prepare 9; path iv) or N-ethyl-N′-(3dimethylaminopropyl)carbodiimide hydrochloride (EDC•HCl) as the condensation reagent, in DCM with DMAP (to prepare 10-13; path iv). 37 The benzyl protecting group in 5 was removed by transfer hydrogenation, using 10% Pd on charcoal as a catalyst and 1,4-cyclohexadiene as a hydrogen donor, in an ethanol/THF (1 : 1) mixture yielding 3 by the indirect way to compare the yields of 3 (path v). Last but not least, product 14 was prepared from 12 by the same transfer hydrogenation as described above (path vi), which was more effective than that mentioned above (path i).…”