Developments in the synthesis of α,α-dibromoacetophenones and related compounds

Arora, Loveena; Prakash, Richa; Pundeer, Rashmi

doi:10.1080/00397911.2019.1579915

Cited by 5 publications

(2 citation statements)

References 52 publications

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“…Apart from the aforementioned strategies, several other traditional and non‐traditional protocols were also developed for the synthesis of gem ‐dihaloketones . Recently two extensive reviews have been published with a focus on the synthesis of α,α‐difluoroketones and α,α‐dibromoketones …”

Section: Synthetic Approaches To αα‐Dihaloketonesmentioning

confidence: 99%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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The α,α‐dihalocarbonyl moiety is a bifunctional system with a gem‐dihalocarbon and a carbonyl carbon in 1,2‐fashion. This is one of the privileged scaffolds in medicinal chemistry due to its chemical and metabolic stability and lipophilicity. They have also been found in numerous structurally divergent natural products and most of their fabricated structures have already been in medicinal use. Apart from their important use in medicinal chemistry, the α,α‐dihalocarbonyl groups have been employed as key building blocks for the development of novel synthetic strategies and utilized as intermediates in total synthesis. In addition to the traditional transformations such as oxidations, reductions, and C−C bond formations, recently several new and non‐classical reactions have also been developed. This review provides short description of existing methods for their synthesis and detailed discussion on the efforts for the discovery and development of new reactions by employing α,α‐dihaloketones as synthetic building blocks. We have presented their use as key functional groups for the synthesis of polycyclic systems of medicinal and material importance and natural products.

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Section: Synthetic Approaches To αα‐Dihaloketonesmentioning

confidence: 99%

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

Sadhukhan

Santhi

Baire

2020

Chemistry A European J

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“…Use of α,α‐dibromoketones as efficient precursors for the synthesis of heterocyclic compounds is gaining increasing attention because of their stability and selectivity in the reactions . In the present study, α,α‐dibromoacetophenones are used for the construction of thiazole nucleus applying modified Hantzsch thiazole synthesis (HTS) .…”

Section: Introductionmentioning

confidence: 99%

α,α‐Dibromoketone precursors in the synthesis of some new thiazole derivatives: Thiazol‐2‐yl hydrazonobutanoates, thiazol‐2‐yl pyrazole‐4‐carboxylates and acids

Kiran

Joshi

Pundeer

2020

Journal of Heterocyclic Chem

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In the present study, α,α-dibromoacetophenones are used as efficient precursors for the facile synthesis of several new hydrazonothiazoles, ethyl 3-((4-arylthiazol-2-yl)hydrazono)butanoates, which undergo Vilsmeier-Haack cyclization to obtain thiazolylpyrazole esters, ethyl 3-methyl-1-(4-arylthiazol-2-yl)-1H-pyrazole-4carbxylates, basic hydrolysis of which gives the corresponding acids, 3-methyl-1-(4-arylthiazol-2-yl)-1H-pyrazole-4-carbxylic acids. All these compounds are tested for antibacterial activity against Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis; Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa and antifungal activity against Saccharomyces cerevisiae and Candida albicans.

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A Switchable Protocol for Selective Synthesis of gem‐Dibromo Compounds and Amides from Ketoximes using TsNBr₂

et al. 2022

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A base controlled metal‐free method for selective synthesis of N‐substituted amide and α,α–dibromoketones have been developed by treating ketoximes with N,N‐dibromo‐p‐toluenesulfonamide (TsNBr2) within a very short reaction time. Interesting feature of the process is that the product selectivity can be switched just by addition or exclusion of the base under the identical reaction condition. It was found that addition of a base in the reaction mixture drives the reaction towards a pathway which is completely different from that without having the additive in the medium. Additionally, another novel strategy has also been developed for synthesis of 1‐(dibromomethyl)benzenes directly from aldehyde using TsNHNH2 and TsNBr2 under metal‐free condition.

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Developments in the synthesis of α,α-dibromoacetophenones and related compounds

Cited by 5 publications

References 52 publications

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

α,α‐Dibromoketone precursors in the synthesis of some new thiazole derivatives: Thiazol‐2‐yl hydrazonobutanoates, thiazol‐2‐yl pyrazole‐4‐carboxylates and acids

A Switchable Protocol for Selective Synthesis of gem‐Dibromo Compounds and Amides from Ketoximes using TsNBr₂

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Developments in the synthesis of α,α-dibromoacetophenones and related compounds

Cited by 5 publications

References 52 publications

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

The α,α‐Dihalocarbonyl Building Blocks: An Avenue for New Reaction Development in Organic Synthesis

α,α‐Dibromoketone precursors in the synthesis of some new thiazole derivatives: Thiazol‐2‐yl hydrazonobutanoates, thiazol‐2‐yl pyrazole‐4‐carboxylates and acids

A Switchable Protocol for Selective Synthesis of gem‐Dibromo Compounds and Amides from Ketoximes using TsNBr2

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A Switchable Protocol for Selective Synthesis of gem‐Dibromo Compounds and Amides from Ketoximes using TsNBr₂