Synthesis and Structure-Activity Relationships of Selected Isomeric Oxime O-Ethers as Anticholinergic Agents

Haney, W.G.; Brown, Robert G.; Isaacson, Eugene I.; Delgado, Jaime N.

doi:10.1002/jps.2600661125

Cited by 17 publications

(6 citation statements)

References 8 publications

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“…The synthesis of the benzaldoxime esters 1 , 2 , and 3 was a simple two‐step process without elaborate reaction conditions. For their preparation, benzaldoxime was synthesized similar to the method of Haney et al18 as starting material in 95% yield. Formation of oxime esters was performed by addition of 1.5 equiv of the corresponding acid chloride to benzaldoxime (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

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Alternative initiators for bimolecular photoinitiating systems

Dworak

Liska

2010

J. Polym. Sci. A Polym. Chem.

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Typical bimolecular photoinitiators (PIs) for radical polymerization of acrylates show only poor photoreactivity because of the unwanted effect of back electron transfer. Therefore, a PI system consisting of benzaldoxime esters and 4-methyl benzophenone was investigated by photo-differential scanning calorimetry experiments. Surprisingly, reactivities are comparable to that of classical monomolecular Type I PIs like Darocur 1173, probably because of an energy transfer from the triplet state of the benzophenone-based sensitizer to the oxime ester initiator. Furthermore, sufficient thermal stability was proven by TGA and storage stability experiments of a resin formulation under elevated temperature. V C 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: [5865][5866][5867][5868][5869][5870][5871] 2010

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Section: Resultsmentioning

confidence: 99%

“…Benzaldoxime,18 O ‐benzoyl benzaldoxime ester 1 ,25 and O ‐methyl benzaldoxime ester 2 15 were synthesized according to procedures described in literature in 95, 33, and 58% yield, respectively. All spectroscopic data were in agreement with the reported data.…”

Section: Methodsmentioning

confidence: 99%

Alternative initiators for bimolecular photoinitiating systems

Dworak

Liska

2010

J. Polym. Sci. A Polym. Chem.

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“…(E)-Acetophenone O-Naphthalen-1-ylmethyl Oxime (2 b) Following the general procedure starting from 2 (0.68 g, 5mmol), oxime ether 2b was obtained as ay ellow oil (1.33 g, 96 %). 1 (E)-Acetophenone O-2-(Dimethylamino)ethyl Oxime (2 c) [24] Following the general procedure starting from 2 (0.68 g, 5mmol), oxime ether 2c was obtained as ay ellow oil (0.96 g, 93 %). 1…”

Section: Methodsmentioning

confidence: 99%

“…[23] In the reactiono fa cetophenone oxime with 2chloro-N,N-dimethylethylamine hydrochloride and NaH in ethanol, the reaction is carriedo ut for 48 ha tr eflux. [24] Reactive benzylc hlorides reactf aster with the oximes (NaH/DMF) and at lower temperatures. [25] For the reactiono fa lkyl bromides with oximes,t he reactions may be carriedo ut at room temperature (NaOH/benzene) [26] and some functionalized alkyl bromides require heatingo ft he reactionm ixture at reflux for 2h (K 2 CO 3 /acetone + toluene).…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2018

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In this study, we present a convenient method for the synthesis of oxime ethers by reacting oximes with various chlorides (alkyl, functionalized alkyl, and benzyl) and with the subsequent use of a super base—pulverized potassium hydroxide in DMSO. The reactions take place at room temperature and the products are obtained in high yields. The final products were received within 2 min to 3 h. In addition, the compounds do not require chromatographic separation. The structure elucidation of the titled compounds was performed by using 1H NMR and 13C NMR spectroscopy as well as mass spectrometry. The presented method of synthesis for oxime ethers is environmentally friendly, because neither water cooling or heating of the reaction mixture/solvents (necessary for chromatographic purification) is required. The synthesis can be carried out very easily on a large scale.

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“…II existe dans la litterature des syntheses qui conduisent au melange des isomeres E et 2 (2). Toutefois, chacun des isomeres a pu &re complexe, soit avec le palladium pour I'isombre Z(3), soit avec le cobalt, le nickel, le cuivre ou I'argent pour I'isomere E(4).…”

Section: Introductionunclassified

Etude De La Conformation D'oximes Thiopheniques

Oussaid

Fayet

Pelletier

et al. 1992

Bulletin des Soc Chimique

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The condensation of 2,5-diformylthiophene with hydroxylamine hydrochloride leads to the formation of three isomers. Two isomers 1' and 1" present a second order axis of symmetry; compound 1' is present with the configuration ZZ and exists in the conformation a and compound 1" is present with the configuration EE and exists in the conformation b. The last isomer 1"' presents the e (2,E) conformation. INTRODUCTIONLa 2-thiophene aldoxime peut exister, soit sous la configuration 2 (ou anti), soit sous la configuration E (ou syn.).

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Synthesis and Structure-Activity Relationships of Selected Isomeric Oxime O-Ethers as Anticholinergic Agents

Cited by 17 publications

References 8 publications

Alternative initiators for bimolecular photoinitiating systems

Alternative initiators for bimolecular photoinitiating systems

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

Etude De La Conformation D'oximes Thiopheniques

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