Selective Bromination of Dehydroacetic Acid with<i>N</i>-Bromosuccinimide

Kumar, Ajay; Lohan, Poonam; Prakash, Om

doi:10.1080/00397911.2011.566461

Cited by 10 publications

(5 citation statements)

References 29 publications

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“…There are several approaches for α-bromination of carbonyl compounds using NBS as the brominating agent. − The use of a radical initiator is a common approach for such α-bromination reactions. ,, However, this particular reaction can also be carried out in strongly basic media − or in acidic media . Lewis acids such as Mg(ClO 4 ) 2 can be used as catalysts for similar transformations.…”

Section: Bromination Reactionsmentioning

confidence: 99%

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: Bromination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…To the best of our knowledge, among the various reagents, which avoid the use of bromine and have been used for selective bromination of other ketones. Only one reagent system, that is, NBS in combination with p ‐TsOH under various conditions has been reported for selective α‐monobromination and α,α‐dibromination of DHA . Based on our recent success on selective dibromination of electron‐rich ketones such as o / p ‐hydroxyacetophenones by the method of King and Ostrum involving heterogeneous reagent system CuBr 2 /CHCl 3 ‐EtOAc, we attempted bromination of DHA by this method.…”

Section: Resultsmentioning

confidence: 99%

“…Because of availability of several reactive sites for nucleophilic and elecrophilic attack, problems of selectivity are generally encountered in the reactions of DHA. For example, bromination of DHA gives different brominated products depending upon the nature of reagent and conditions employed in the reaction. The reported results are summarized in Chart 2.…”

Section: Introductionmentioning

confidence: 99%

Selective Synthesis of 3‐(α,α‐Dibromoacetyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one as an Excellent Precursor for the Synthesis of 2‐Substituted 4‐(4‐Hydroxy‐6‐methyl‐2H‐2‐oxopyran‐3‐yl)thiazoles as Antimicrobial and Antifungal Agents

Kapoor

Prakash

Kumar

et al. 2018

Journal of Heterocyclic Chem

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A selective synthesis of 3-(α,α-dibromoacetyl)-4-hydroxy-6-methyl-2H-pyran-2-one (3) has been achieved by bromination of DHA using CuBr 2 /CHCl 3 -EtOAc. The reaction of 3 with different thioureas/thiomides/thiosemicarbazide offers a convenient and efficient method for the syntheses of 2-substituted 4-(4-hydroxy-6-methyl-2H-2-oxopyran-3-yl)thiazoles. These thiazoles were evaluated for their antimicrobial and antifungal activity.

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“…The IUPAC name of dehydroacetic acid is 3-Acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 40 . Dehydroacetic acid can be utilized for synthesizing several biologically active compounds 41 . The products derived from dehydroacetic acid have multiple applications in the food, cosmetic and pharmaceutical industry 42 .…”

Section: Introductionmentioning

confidence: 99%

Evaluation of antibiofilm properties of dehydroacetic acid (DHA) grafted spiro-oxindolopyrrolidines synthesized via multicomponent 1,3-dipolar cycloaddition reaction

Suresh Babu,

Sharma,

Athira

et al. 2023

Sci Rep

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The current work involves the use of dehydroacetic acid based chalcone derivatives for the synthesis of spirooxindole grafted pyrrolidine moieties. All the synthesized compounds have been characterized using spectroscopic techniques such as NMR (1H-NMR and 13C-NMR), IR, mass and elemental analysis. Molecular mechanics studies were performed to comprehend the regioselectivity in the product formation. Molecular docking of the synthesized compounds was performed with few bacterial proteins of Bacillus subtilis and Pseudomonas aeruginosa responsible for biofilm formation followed by molecular dynamics simulations with the potential lead compound. Further, to corroborate the results obtained via in silico study, anti-biofilm activity etc. of the synthesized compounds (4a–e) was checked for effectiveness against biofilm formation. Taken together, this study opens up to explore these compounds’ multiple roles in diverse fields in the arena of medical sciences.

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Selective Bromination of Dehydroacetic Acid withN-Bromosuccinimide

Cited by 10 publications

References 29 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Selective Synthesis of 3‐(α,α‐Dibromoacetyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one as an Excellent Precursor for the Synthesis of 2‐Substituted 4‐(4‐Hydroxy‐6‐methyl‐2H‐2‐oxopyran‐3‐yl)thiazoles as Antimicrobial and Antifungal Agents

Evaluation of antibiofilm properties of dehydroacetic acid (DHA) grafted spiro-oxindolopyrrolidines synthesized via multicomponent 1,3-dipolar cycloaddition reaction

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