1,3‐Dibromo‐5,5‐dimethylhydantoin (DBH) as an efficient promoter for acetylation of 3‐arylsydnones in the presence of acetic anhydride under neutral conditions

Azarifar, Davood; Bosra, Hassan Ghasemnejad; Tajbaksh, Mahmood

doi:10.1002/jhet.5570440231

Cited by 24 publications

(5 citation statements)

References 24 publications

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“…2245 DBH has also found applications as a catalyst in the oxidations of pyrazolines. 2246 Conversion of various 3-arylsydnones to their corresponding 4-acetyl derivatives was achieved using DBH as the catalyst (Scheme 840). 2247 The products were achieved by treating the precursor 3-arylsydnones with acetic anhydride in the presence of a catalytic amount of DBH at reflux temperature.…”

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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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confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…DBH has been found to efficiently catalyze the conversion of various 3-arylsydnones to their corresponding 4-acetyl derivatives in the presence of acetic anhydride under neutral conditions in satisfactory yields (Scheme 94) [110]. …”

Section: Scheme 92mentioning

confidence: 99%

Application of N-halo reagents in organic synthesis

Kolvari

Ghorbani‐Choghamarani

Salehi

et al. 2007

JICS

157

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This review article summarizes published data on the application of N-halo reagents (such as N-halo amines, N-halo amides and/or imides, N-halo sulfonamides and/or imides, and etc.) in various organic functional group transformations such as: oxidation reactions, deprotection and protection of different functional groups, halogenation of saturated and unsaturated compounds, acylation of alcohols, phenols, amines or thiols, epoxidation of alkenes, aziridination and etc. The main purpose of writing this review is encouraging of active researchers interested to this field for the synthesis of new N-halo reagents specially with different halogens and applications of these new N-halo reagents in organic reactions or finding more and more applications of existing N-halo reagents in organic synthesis.

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“…Thirdly, other researchers proved that acetic anhydride can convert the dextro-rotary N-nitroso-N-phenylalanine into the optically inactive N-phenyl-C-methylsydnone (IV). The loss of optical activity implies either racemization or a change in the hybridization of C4 from a chiral sp 3 . The oxygen atom attached to C5 was proved to be in an enolate form due to the rapid formation of a monobromo derivative (V) in glacial acetic acid and bromine [10].…”

Section: Definition Of Sydnonementioning

confidence: 99%

“…The most potent agents were found to have a chloride or methyl substituent on the stilbene moiety with a phenyl or methyl group at C4 of the sydnone ring like in structures XXXVIII and XXXIX [61]. Others reported a significant anticancer activity for new sydnones derivatized with imidazo [2,1-b] [1,3,4] thiadiazole and coumarin at C4 of the sydnone ring (XL) against HT-29 human colorectal adenocarcinoma cell line. They found that the hydrophobicity of R was crucial for the cytotoxic activity and the existence of a chlorine atom on the coumarin ring (R 1 ) sharply raised the activity to be comparable to that of cisplatin [62].…”

Section: Cytotoxic and Anticancer Activitymentioning

confidence: 99%

“…Many reports stated that one covalent structure is not sufficient to represent the sydnone molecule satisfactorily [1,2]. However, 1,2,3-oxadiazolium bearing a carbonyl function has recently been the major representative of sydnones because FTIR spectroscopy showed a carbonyl stretch frequency attached to C5 of the ring like in 4-acetyl-3-tolylsydnone which exhibited a strong band at 1783 cm -1 Chemistry of sydnone [3]. X-ray analysis revealed a bond length of 1.196 Å which corresponds to an exocyclic C=O double bond [4].…”

Section: Introductionmentioning

confidence: 99%

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Mesoionic Sydnone: A Review in Their Chemical and Biological Properties

Abdualkader

Taher

Yusoff

2017

Int J Pharm Pharm Sci

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Various literature sources have documented sydnones as important molecules with exclusive chemical properties and a wide spectrum of bioactivities. Sydnone can be defined as a five-membered pseudo-aromatic heterocyclic molecule. Classically, 1,2,3-oxadiazole forms the main skeleton of sydnone. The molecule has delocalized balanced positive and negative charges. The five annular atoms share the positive charge and the enolate-like exocyclic oxygen atom bears the negative charge. The hydrogen atom at the position C4 was proved to have acidic and nucleophilic functionalities making the sydnone ring reactive towards electrophilic reagents. These unique chemical features enable sydnones to interact with biomolecules resulting in important therapeutic effects like anticancer, antidiabetic, antimicrobial, antioxidant and anti-inflammatory. Consequently, we aim from the current article to review the available chemical and pharmacological information on sydnone and its derivatives.

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1,3‐Dibromo‐5,5‐dimethylhydantoin (DBH) as an efficient promoter for acetylation of 3‐arylsydnones in the presence of acetic anhydride under neutral conditions

Abstract: 1,3‐Dibromo‐5,5‐dimethylhydantoin (DBH) has been found to efficiently promote the conversion of various 3‐arylsydnones to their 4‐acetyl congeners in the presence of acetic anhydride under neutral conditions in satisfactory yields.

Cited by 24 publications

References 24 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Application of N-halo reagents in organic synthesis

Mesoionic Sydnone: A Review in Their Chemical and Biological Properties

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