Bromamine-T/RuCl3 as an efficient system for the oxidation of tertiary amines to N-oxides

Sharma, Vishal B.; Jain, Suman L.; Sain, Bir

doi:10.1016/j.tetlet.2004.04.014

Cited by 26 publications

(8 citation statements)

References 26 publications

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“…1668 Bromamine-T is a good oxidant which can be prepared by treating an aqueous solution of chloramine-T trihydrate with bromine at room temperature followed by the addition of aqueous NaOH to the precipitate of dibromamine-T. 1669 A variety of tertiary amines were efficiently and selectively oxidized to the corresponding N-oxides by bromamine-T using ruthenium trichloride as the catalyst at 80 °C (Scheme 593). 1670 The reaction was highly dependent on the pH of the reaction. The best condition was pH 8.4.…”

Section: Oxidation Reactions Using Other Bromo-organic Compoundsmentioning

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: Oxidation Reactions Using Other Bromo-organic Compoundsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…The reaction gives high yields with both electron-rich and electron-deficient pyridines (Eq. The same research group had previously reported a related Re-catalyzed N-oxidation with bromamine-T as the terminal oxidant [126]. The latter system also worked well with N,N-dialkylated anilines to give the corresponding N-oxides.…”

Section: ð8:26þmentioning

confidence: 75%

Selective Oxidation of Amines and Sulfides

Bäckvall

2010

Modern Oxidation Methods

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A large number of methods are known in the literature for the oxidation of sulfides (thioethers) to sulfoxides by electrophilic reagents. These include the use of peracids [10], NaIO 4 , hypochlorites, MnO 2 , CrO 3 , SeO 2 , and iodosobenzene. The use of these reagents has been reviewed up to 2005 [3, 4]. Hydrogen peroxide can also be used as a direct oxidant, although this reaction is slow in the absence of catalyst. Its use in catalytic reactions is discussed below in Section 8.2.2. 7 5 9 9 5 Ph S 8 15 94 280j 8 Selective Oxidation of Amines and Sulfides

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“…Although the exact mechanism of this synthetic protocol is not clear, the mechanism depicted in Figure 9 shows the role of nanocatalyst in promoting the synthesis of minoxidil in a two-step procedure. The figure shows that due to the Lewis acidity of transition metals existing in spinel ferrites, 6-chloro-2,4-diaminopyrimidine interacted with the surafce of nanocatalyst [27][28][29][30][31][32]. Then, by the addition of H 2 O 2 and its interaction with the surface of nanocatalyst, N -oxidation of pyrimidine ring was carried out giving 2,6-diamino-4-chloro-pyrimidine N -oxide.…”

Section: Synthesis Of 24-diamino-6-piperidinopyrimidine 3-oxidementioning

confidence: 99%

The promoted synthesis of minoxidil by magnetic nanoparticles of cobalt ferrite(CoFe2O4) as a heterogeneous reusable catalyst

Eisavi¹,

Ahmadi²,

Zeynizadeh³

et al. 2019

Turk J Chem

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Minoxidil (2,4-diamino-6-piperidinopyrimidine 3-oxide) was primarily recognized as a drug for reducing vascular resistance to blood flow. It was later introduced as a more important medicine for topical stimulation of hair growth and baldness reverting as well as treatment of androgenic alopecia through increasing prostaglandin endoperoxide synthesis. In this study, magnetic nanoparticles (MNPs) of spinel ferrites (MFe 2 O 4 , M = Co, Ni, Fe, Cu, and Zn) via solid-state grinding procedure were prepared and then characterized using X-ray diffraction, scanning electron microscopy, transmission electron microscopy, vibrating sample magnetometer, and Fourier transform infrared techniques. The prepared nanoferrites were utilized as efficient and green heterogeneous catalysts for N-oxidation of 2,6-diamino-4chloro-pyrimidine with H 2 O 2 in refluxing ethanol giving 2,6-diamino-4-chloro-pyrimidine N-oxide as a starting material for the synthesis of 2,4-diamino-6-piperidinopyrimidine 3-oxide (minoxidil). Among the examined nanoferrites, CoFe 2 O 4 MNPs exhibited prominent catalytic activity giving the product in 95% yield within 60 min. Moreover, the reusability of nano-CoFe 2 O 4 was examined for 6 consecutive cycles without significant loss of catalytic activity and magnetic property.

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Bromamine-T/RuCl3 as an efficient system for the oxidation of tertiary amines to N-oxides

Cited by 26 publications

References 26 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Selective Oxidation of Amines and Sulfides

The promoted synthesis of minoxidil by magnetic nanoparticles of cobalt ferrite(CoFe2O4) as a heterogeneous reusable catalyst

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