Regioselectivity in free radical bromination of unsymmetrical dimethylated pyridines

Thapa, Rajesh; Brown, Jordan; Balestri, T.; Taylor, Richard T.

doi:10.1016/j.tetlet.2014.08.069

Cited by 9 publications

(5 citation statements)

References 76 publications

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“…653 The Taylor group recently reran the NBS-mediated free radical bromination of picolines along with lutidines to establish a better understanding of the mechanism and regioselectivity of the bromination process. 654 Bromination of cumene with NBS yielded 1,2-dibromo-2phenylpropane, whereas 4-hydroxycumene gave 3-bromo-4hydroxycumene, 3,5-dibromo-4-hydroxycumene, or 1,3-dibromo-2-(3,5-dibromo-4-hydroxyphenyl)propene depending on the amount of reagent used. 655 Similarly, 4-hydroxy-3,5-di-tertbutylcumene gave either 1,3-dibromo-2-(4-hydroxy-3,5-di-tertbutylphenyl)propene or 1,3-dibromo-2-(2-bromo-4-oxo-3,5-ditert-butylcyclohexa-2,5-dienyl)propene.…”

Section: Saldabols Et Al Carried Out Bromination Of Imidazothiazolesmentioning

confidence: 99%

“…In the case of picolines, photobromination in an aqueous biphasic medium occurs more efficiently in dichloromethane or benzene as compared to classical carbon tetrachloride . The Taylor group recently reran the NBS-mediated free radical bromination of picolines along with lutidines to establish a better understanding of the mechanism and regioselectivity of the bromination process …”

Section: Bromination Reactionsmentioning

confidence: 99%

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Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

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Section: Saldabols Et Al Carried Out Bromination Of Imidazothiazolesmentioning

confidence: 99%

Section: Bromination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…This is common to numerous radical bromination protocols. [41] It was found that if 1.2 equiv. of NBS was added in batches in the amount of 1/3 portions every 1.5 h to the gently refluxing CCl 4 solution, 22% increase in the product 71% yield was achieved after the reaction was complete with a small amount of byproduct.…”

Section: Resultsmentioning

confidence: 99%

A Facile Synthesis and M. tuberculosis Leucyl-tRNA Synthetase Inhi-bitory Activity of Novel 3-Arylvinylquinoxaline-2-carboxylic Acids

Li¹,

Dong²,

Qin³

et al. 2020

Chin. J. Org. Chem.

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In the present work, a simple and facile synthesis of a new series of 3-arylvinylquinoxaline-2-carboxylic acids has been achieved using the newly-synthesized ethyl 3-bromomethylquinoxaline-2-carboxylate as substrate through one-pot sequential Arbuzov/Horner-Wadsworth-Emmons (HWE)/ester hydrolysis reaction procedure. A primary in vitro evaluation for their inhibitory activity against Mycobacterium smegmatis (M. smegmatis) Leucyl-tRNA synthetase (Mtb LeuRS) revealed that (E)-3-(3-nitrostyryl)quinoxaline-2-carboxylic acid (5j) represented the most active compound in this round of effort with the IC 50 value of 14.7 μmol•L-1 , which was much superior to the reference drug AN2679, indicating the potential medicinal value for the exploration of novel Mtb LeuRS inhibitor. The results of molecular docking analyses using CDOCKER module of Discovery Studio (DS) software suggested that it could bind well to the active site of Mtb LeuRS. Moreover, the antitubercular assay against M. smegmatis also revealed that the nitro-substituted 5j has the best anti-tubercular activity with the minimum inhibitory concentration (MIC) value 15.6 μg/mL, being comparable with the reference rifampicin.

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“…More difficulty has been experienced in finding a symmetrical molecule to serve as solvent in Raman spectroscopy, and as a solvent for reactions of N-bromosuccinimide. Benzotrifluoride (a,a,a-trifluorotoluene, C 6 H 5 CF 3 ) has been touted as a replacement for carbon tetrachloride in this application [4] but it has not been widely adopted. Another use of carbon tetrachloride that is hard to substitute is its use in very small quantities as a liver toxicant in studies of liver function and alcoholism.…”

Section: Laboratory and Analytical Uses Of Carbon Tetrachloridementioning

confidence: 99%

Substance Abuse: Carbon Tetrachloride and the Ozone Layer

Rae¹

2016

Aust. J. Chem.

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Each year, ~200000 tonnes of carbon tetrachloride are produced and consumed as a solvent, a starting material for synthesis, or in standard methods of analysis. Because it is an ozone-depleting substance, this information is reported on an annual basis to the Montreal Protocol, under which it is a ‘controlled’ substance. Replacing emissive uses of carbon tetrachloride with ozone-friendly chemicals is proceeding slowly. One example is the use of tetrachloroethylene as a replacement for carbon tetrachloride in oil and grease analysis by infrared spectroscopy. Overall, however, there is more carbon tetrachloride in the upper atmosphere than can be accounted for in terms of known uses and emissions. The discrepancy is the subject of intensive and repeated investigation by atmospheric scientists.

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Regioselectivity in free radical bromination of unsymmetrical dimethylated pyridines

Cited by 9 publications

References 76 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

A Facile Synthesis and M. tuberculosis Leucyl-tRNA Synthetase Inhi-bitory Activity of Novel 3-Arylvinylquinoxaline-2-carboxylic Acids

Substance Abuse: Carbon Tetrachloride and the Ozone Layer

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