Acylation of Grignard reagents mediated by N-methylpyrrolidone: A remarkable selectivity for the synthesis of ketones

Gowda, Maravanhalli Sidde; Pande, Sushanth Sudhir; Ramakrishna, Ramesha; Prabhu, Kandikere Ramaiah

doi:10.1039/c1ob05780d

Cited by 24 publications

(10 citation statements)

References 47 publications

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“…Finally, the synthesis of the mono cationic MB327 analogue 5 could be accomplished in two steps starting from chloropropanone 35 (Scheme ) . Reduction of the keto function with Et 3 SiH in TFA at 75 °C under microwave irradiation following a procedure adapted from Perlmutter et al.…”

Section: Resultsmentioning

confidence: 99%

“…Finally,t he synthesis of the mono cationicM B327 analogue 5 could be accomplished in two steps startingf rom chloropropanone 35 (Scheme 3). [18][19][20][21][22][23][24][25][26][27][28][29] Reduction of the keto function with Et 3 SiH in TFAa t7 58Cu nder microwave irradiationf ollowing ap rocedure adapted from Perlmutter et al led to chloropropylb enzene 36 in 90 %y ield. [21] Subsequent treatment of 36 with 4-tert-butylpyridine in the presence of stoichiometric amountso fN aI (16 h, 90 8C) and ion-exchange reaction with Amberlite IRA-410 in its chloride form provided target compound 5 in 81 %y ield.…”

Section: Entrymentioning

confidence: 99%

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Synthesis of a Series of Non‐Symmetric Bispyridinium and Related Compounds and Their Affinity Characterization at the Nicotinic Acetylcholine Receptor

et al. 2018

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The current standard therapy to counteract organophosphate intoxication is not effective in equal measure against all types of organophosphorus compounds (OPCs), as the outcome of oxime‐induced reactivation of inactivated acetylcholinesterase (AChE) strongly depends on the particular OPC. In case the reactivation is insufficient, acetylcholine concentrations that rise to pathophysiological levels force the nicotinic acetylcholine receptor (nAChR) into a desensitized state and hence a functionally inactive state. As a consequence, neurotransmission is irreversibly disrupted at the neuromuscular junction. Previous electrophysiological studies identified the symmetric bispyridinium compound 1,1′‐(propane‐1,3‐diyl)bis[4‐(tert‐butyl)pyridin‐1‐ium] diiodide (MB327) as a re‐sensitizer of the desensitized nAChR. MB327 is thereby capable of restoring the functional activity. Very recently, in silico modeling studies suggested non‐symmetric derivatives of MB327 as potential re‐sensitizers with enhanced binding affinity and thus possible enhanced efficacy. In this study, 26 novel non‐symmetric bispyridinium compounds and related derivatives were synthesized. For the synthesis of the highly polar target compounds in sufficient quantities, newly developed and highly efficient two‐step procedures were used. Compounds were characterized in terms of their binding affinity toward the MB327 binding site at the nAChR using recently developed mass spectrometry (MS) Binding Assays. Regarding structure–affinity relationships at the MB327 binding site, the presence of two quaternary aromatic nitrogen centers as well as pyridinium systems with a tert‐butyl group at the 4‐position or a NMe2 group at the 3‐ or 4‐positions appeared to be beneficial for high binding affinities.

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Section: Resultsmentioning

confidence: 99%

Section: Entrymentioning

confidence: 99%

Synthesis of a Series of Non‐Symmetric Bispyridinium and Related Compounds and Their Affinity Characterization at the Nicotinic Acetylcholine Receptor

et al. 2018

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“…According to this procedure, higher values for PF and PR indicate fewer problems in the respective domain. In a last step, scores for PF and PR were transformed to values between 0 and 100, according to equation (1) [25]:…”

Section: Methodsmentioning

confidence: 99%

Questionnaire-based approach to assess schoolchildren's physical fitness and its potential role in exploring the putative impact of helminth and Plasmodium spp. infections in Côte d'Ivoire

et al. 2011

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BackgroundDisability weights (DWs) are important for estimating burden of disease in terms of disability-adjusted life years. The previous practice of eliciting DWs by expert opinion has been challenged. More recent approaches employed quality of life (QoL) questionnaires to establish patient-based DWs, but results are ambiguous.MethodsIn early 2010, we administered a questionnaire pertaining to physical fitness to 200 schoolchildren in Côte d'Ivoire. Helminth and Plasmodium spp. infections were determined and schoolchildren's physical fitness objectively measured in a maximal multistage 20 m shuttle run test. Associations between objectively measured and self-reported physical fitness and between self-reported physical fitness and infection status were determined. Spearman rank correlation coefficient, uni- and multivariable linear regression models adjusting for children's age and sex, ambient air temperature and humidity, Fisher's test, χ² and t-test statistics were used for statistical analysis.ResultsThe prevalence of Schistosoma haematobium, Plasmodium spp., Schistosoma mansoni, hookworm and Ascaris lumbricoides in 167 children with complete parasitological results was 84.4%, 74.9%, 54.5%, 14.4% and 1.2%, respectively. High infection intensities and multiple species parasite infections were common. In the 137 children with complete data also from the shuttle run test, we found statistically significant correlations between objectively measured and self-reported physical fitness. However, no statistically significant correlation between the children's parasitic infection status and self-reported physical fitness was identified. An attrition analysis revealed considerably lower self-reported physical fitness scores of parasitized children who were excluded from shuttle run testing due to medical concerns in comparison to parasitized children who were able to successfully complete the shuttle run test.ConclusionsOur QoL questionnaire proofed valid to assess children's physical fitness in the current study area. Reasons why no differences in self-reported physical fitness in children with different parasitic infections were found are manifold, but do not preclude the use of QoL questionnaires in the elicitation of DWs. Indeed, the questionnaire was particularly useful in assessing physical fitness of those children, who were - supposedly due to parasitic infections - unable to complete the shuttle run test. Hence, we encourage others to use QoL questionnaires to determine not only physical fitness, but also more subtle morbidities.

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“…It is also a common catalyst [35][36][37][38] used in the synthesis of acyl halides, in particular, and in the synthesis of acyl chloride from carboxylic acids using oxalyl or thionyl chloride. The catalytic mechanism entails reversible formation of an imidoyl chloride.…”

Section: Introductionmentioning

confidence: 99%

Beyond a solvent: triple roles of dimethylformamide in organic chemistry

2018

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N,N-Dimethylformamide (DMF) is frequently used as an aprotic solvent in chemical transformations in laboratories of academia as well as in those of chemical industry. In the present review, we will reveal that DMF is actually something much more than a solvent. It is a unique chemical since, as well as being an effective polar aprotic solvent, it can play three other important roles in organic chemistry. It can be used as a reagent, a catalyst, and a stabilizer.

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Acylation of Grignard reagents mediated by N-methylpyrrolidone: A remarkable selectivity for the synthesis of ketones

Cited by 24 publications

References 47 publications

Synthesis of a Series of Non‐Symmetric Bispyridinium and Related Compounds and Their Affinity Characterization at the Nicotinic Acetylcholine Receptor

Synthesis of a Series of Non‐Symmetric Bispyridinium and Related Compounds and Their Affinity Characterization at the Nicotinic Acetylcholine Receptor

Questionnaire-based approach to assess schoolchildren's physical fitness and its potential role in exploring the putative impact of helminth and Plasmodium spp. infections in Côte d'Ivoire

Beyond a solvent: triple roles of dimethylformamide in organic chemistry

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