The Use of N-Bromosuccinimide and Pyridinium Bromide Perbromide in the Conversion of Flavonones Into Flavones

Lorette, N. B.; Gage, Thomas B.; Wender, Simon H.

doi:10.1021/jo01146a016

Cited by 18 publications

(7 citation statements)

References 4 publications

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“…Lorette et al used this reagent in flavonoid chemistry. 967 They converted acetylated hesperidin and naringin into diosmin and apigenin-7-rhamnoglucoside, respectively, by bromination with pyridinium bromide perbromide. The method presented, in addition to giving satisfactory yields, had additional advantages over older procedures from the standpoint of the ease of handling of the brominating agent, the simple equipment required, and the ease of purification of the product.…”

Section: -Bromo-55-dimethylhydantoinmentioning

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: -Bromo-55-dimethylhydantoinmentioning

confidence: 99%

“…They also brominated phenol and aniline in the 2-, 4-, and 6-positions. Lorette et al used this reagent in flavonoid chemistry . They converted acetylated hesperidin and naringin into diosmin and apigenin-7-rhamnoglucoside, respectively, by bromination with pyridinium bromide perbromide.…”

Section: Bromination Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…The dehydrogenation of flavanones and flavanone glycosides to the corresponding flavone compounds has been achieved in several instances (9,23,24,106,107,137,138).…”

Section: LVII Lixmentioning

confidence: 99%

Oxidations and Dehydrogenations with N-Bromosuccinimide and Related N-Haloimides.

Filler¹

1963

Chem. Rev.

210

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“…4 It was purified by separation in large scale vapor phase chromatographic equipment. 6 Its properties were: b.p.…”

Section: Methodsmentioning

confidence: 99%

“…The application of N-bromosuccinimide (NBS) to dehydrogenation of flavanone derivatives has been reported by Lorette,Gage,and Wender,4 who converted flavanone glycosides to flavone glycosides, sild subsequently by a number of workers5 to dehydrogenation OF other flavanone derivatives. I n each case, the essential steps were bromination with N-bromosuccinimide and dehydrohalogenation of the bromination product with an organic or inorganic base.…”

Section: Received October 17 I958mentioning

confidence: 99%

Notes- Pyrolysis of Perfluorothioxane Tetrafluoride

Dresdner¹,

Young²

1959

J. Org. Chem.

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NOTESyol. 24 and the oxidation procedure used for the preparation of 4,6-benzindoIe (V) was followed. The product (IV) was recovered from the steam distillate as white crystals; 0.45 g• (27%), m.p. 170-171°. By recrystallization from dilute ethanol an analytically pure sample (m.p. 172°) was prepared which gave a very strong positive test with Ehrlich's reagent. Its infrared spectrum in the 2.9 µ and 6.1 µ regions was similar to that of V.

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The Use of N-Bromosuccinimide and Pyridinium Bromide Perbromide in the Conversion of Flavonones Into Flavones

Cited by 18 publications

References 4 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Oxidations and Dehydrogenations with N-Bromosuccinimide and Related N-Haloimides.

Notes- Pyrolysis of Perfluorothioxane Tetrafluoride

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