ChemInform Abstract: Synthesis and Characterization of para‐Substituted N,N′‐Dihydroxybenzamidines and Their Derivatives as Model Compounds for a Class of Prodrugs.

Schwarz, Laura; Girreser, Ulrich; Clement, Bernd

doi:10.1002/chin.201505098

Cited by 2 publications

(3 citation statements)

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“…Attempts to obtain X-ray quality single crystals of the oxime intermediates or target products proved unsuccessful in this study. However, the oxime geometry was considered to be in the E-configuration, an assumption that is in agreement with published data [ 24 ].…”

Section: Resultssupporting

confidence: 66%

“…Upon addition of sodium hydride, the mixture was placed in an ice bath due to the release of a large amount of heat as the reaction progressed. Next, intermediate 3 was directly converted to the key intermediate, 4 , by treatment with hydroxylamine hydrochloride [ 24 ]. Finally, the corresponding target oxime esters ( 5a – 5s ) were obtained via intermediate 4 and reactions with carboxylic acid functionalities in the presence of dicyclohexylcarbodiimide (DCC) and 4-dimethylaminopyridine (DMAP).…”

Section: Resultsmentioning

confidence: 99%

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Ovicidal and Insecticidal Activities of Pyriproxyfen Derivatives with an Oxime Ester Group

Sun

Shuhui

et al. 2017

Molecules

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Based on the structural framework of a pyriproxyfen metabolite, nineteen oxime ester derivatives were synthesized via reaction of the carboxylic acids with 4-(2-(2-pyridinyloxy)ethoxy)benzaldehyde oxime. The corresponding structures were comprehensively characterized by 1H-nuclear magnetic resonance (NMR), 13C-NMR, and electrospray ionization high-resolution mass spectrometry (ESI-HRMS). All of the compounds were screened for their insecticidal activities against Plutella xylostella and Myzus persicae, and for their ovicidal activities against Helicoverpa armigera eggs. The results obtained show that most of the oxime ester derivatives displayed moderate to high insecticidal activities and ovicidal activities at a concentration of 600 μg/mL. In particular, the ovicidal activity of compounds 5j, 5o, 5p, 5q, and 5s was determined to be 100%. Importantly, some of the compounds presented even higher biological activities than the reference compound pyriproxyfen. For example, compound 5j displayed an insecticidal activity value of 87.5% against Myzus persicae, whereas the activity value of pyriproxyfen was 68.3% at a concentration of 600 μg/mL. Among the synthesized compounds 5j and 5s exhibited broad biological activity spectra.

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Section: Resultssupporting

confidence: 66%

Section: Resultsmentioning

confidence: 99%

Ovicidal and Insecticidal Activities of Pyriproxyfen Derivatives with an Oxime Ester Group

Sun

Shuhui

et al. 2017

Molecules

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“…10 The nitriles have also been extensively explored as the precursors for the synthesis of a wide range of functional groups including carboxylic acids, 11 carboxamides, 12 tetrazoles, 13 amines, 14 imidazoles, 15 and oximes. 16 Usually, the preparation of nitriles from aryl halides was carried out using (i) a stoichiometric amount of CuCN at 150−250 °C17,18 and (ii) by the reaction of toluene derivative with oxygen and ammonia at high temperature (300−550 °C) using a fixed-bed heterogeneous catalytic approach. 19,20 In some cases, the aryl halides were used as the precursors and the cyanation was performed by using highly toxic reagents such as KCN, 20 NaCN, 21,22 CuCN, 23,24 Zn(CN) 2 , 25−27 and acetone cyanohydrins.…”

Section: ■ Introductionmentioning

confidence: 99%

Hybrid Cobalt Doped-Cerium Oxide as a Multifunctional Nanocatalyst for Various Organic Transformations

Ghosh

Mohammad

Mobin

2019

ACS Sustainable Chem. Eng.

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Development of a low-cost, environmentally benign and robust catalyst for multipurpose industrially relevant organic transformations is highly desirable for the sustainable future of chemical industries. A hybrid cobalt doped-cerium oxide nanocatalyst (Co@CeO2NC) was prepared via simple coprecipitation method using water as the solvent. The characterization of Co@CeO2NC was performed using different techniques such as XRD, TGA, FE-SEM, HR-TEM, EDAX-mapping, BET, and XPS analysis. The structural characterization of the prepared sample by XRD and XPS analysis revealed the presence of the mixed phase of cobalt oxide and cobalt doped-cerium oxide as a hybrid (Co@CeO2NC). Industrially relevant organic transformations such as (i) nitrile formation using aldehyde with hydroxylamine hydrochloride, (ii) reductive amination of aldehydes to form tertiary N,N-dimethyl amines, and (iii) direct acetylation of alcohols/amines with acetic acid were achieved in an excellent manner using Co@CeO2NC hybrid as the multifunctional catalyst. Excellent catalytic activity of Co@CeO2NC was noticed for the conversion of 4-chlorobenzaldehyde to 4-chlorobenzonitrile with 99% conversion and 99% selectivity and 100% conversion of benzaldehyde to N,N-dimethylbenzylamine using DMF as NMe2 source, reductant, and solvent. Moreover, acetylation of 4-methoxybenzyl alcohol and 2-methyl aniline gave excellent conversion and selectivity toward the formation of −O and −N acetyl. The scope of the Co@CeO2NC was further evaluated for other aldehydes, alcohols, and amines with an excellent conversion and high selectivity.

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ChemInform Abstract: Synthesis and Characterization of para‐Substituted N,N′‐Dihydroxybenzamidines and Their Derivatives as Model Compounds for a Class of Prodrugs.

Cited by 2 publications

References 1 publication

Ovicidal and Insecticidal Activities of Pyriproxyfen Derivatives with an Oxime Ester Group

Ovicidal and Insecticidal Activities of Pyriproxyfen Derivatives with an Oxime Ester Group

Hybrid Cobalt Doped-Cerium Oxide as a Multifunctional Nanocatalyst for Various Organic Transformations

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