Efficient Oxidation of Alcohols to Carbonyl Compounds by <i>N,N</i>‐Dichloro‐4‐Methylbenzenesulfonamide under Mild Conditions

Khazaei, Ardeshir; Raiatzadeh, Ayeh; Rostami, Amin

doi:10.1002/jccs.200700065

Cited by 7 publications

(7 citation statements)

References 22 publications

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“…2 The preparation of tetrahydrobenzo [b]pyrans are important due to their significant anti-coagulant, diuretic, spasmolytic, anti-cancer, antihypertensive, calcium antagonists spasmolytic, pharmaceuticals and anti-anaphylactic properties. [10][11][12] Having above facts and in continuation of our previous studies on the applications of N-halo reagents in organic synthesis, [13][14][15][16][17][18][19][20][21] we [1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD) (Figure 1) as an efficient and homogeneous catalyst for the synthesis of 4H-pyran and pyrazolo [1,2-b] phthalazine and pyranopyrazole derivatives. However, some reported methods for the synthesis of mentioned compounds suffer from one or more of disadvantages such as using toxic, corrosive, expensive and/or large amount of catalysts, long reaction time, toxic and corrosive solvents and strong acidic media.…”

Section: Introductionmentioning

confidence: 87%

N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media

et al. 2015

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An international journal to further the chemical sciencesRSC Advances is an international, peer-reviewed, online journal covering all of the chemical sciences, including interdisciplinary fields.The criteria for publication are that the experimental and/or theoretical work must be high quality, well conducted and demonstrate an advance by adding to the development of the field . It is essential that all research work reported in RSC Advances is well-carried out and wellcharacterised. There should be enough supporting evidence for the claims made in the manuscript. When preparing your report, please:• comment on the originality and scientific reliability of the work;• comment on the characterisation of the compounds/materials reported -has this been accurately interpreted and does it support the conclusions of the work;

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Section: Introductionmentioning

confidence: 87%

N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media

et al. 2015

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“…Some specific features of N-halo reagents including the high activity of the N-X bond and the various modes of splitting of this bond have led to their wide application in organic synthesis. 22 Based on the above facts and in continuation of our previous studies on the application of N-halo reagents in organic synthesis, [23][24][25][26][27][28][29][30][31] we have recently introduced a new N-halo reagent, namely N,2-dibromo-6-chloro-3,4-dihydro-2Hbenzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD), as an efficient and novel catalyst (Scheme 1 and Fig. 1).…”

Section: Introductionmentioning

confidence: 91%

Tandem cyclocondensation-Knoevenagel–Michael reaction of phenyl hydrazine, acetoacetate derivatives and arylaldehydes

2014

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In this work, a novel N-bromo sulfonamide reagent, namely N,2-dibromo-6-chloro-3,4-dihydro-2Hbenzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide (DCDBTSD), is synthesized and fully characterized by IR, UV, 1 H and 13 C NMR, XRD, TG/DTG as well as mass spectra. The presented N-bromo sulfonamide is used as a new and highly efficient catalyst for the synthesis of 4,4 0 -(arylmethylene)-bis(3-methyl-1phenyl-1H-pyrazol-5-ol)s via one-pot pseudo five component condensation reaction of phenylhydrazine, acetoacetate derivatives and arylaldehydes. Mechanistically, Br + ions, which are generated by the catalyst, can catalyze this reaction in neutral media. This methodology offers several advantages, such as use of non-toxic and inexpensive materials, high yields, short reaction times and clean workup.

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“…All products were identified by their GC-MS (GC-Mass, Agilent 5975C) and 1 HNMR spectra (Bruker-Avance AQS 400 MHz spectrometer; in CDCl 3 ) with authentic samples. 23,28,47,49,51 A comparison of the catalytic efficiency of ZPZn with selected previously known catalysts is collected in Table 5. BnOH was oxidized to BzH in less than 30 min at 60°C in 89% isolated yield using the present protocol (Table 5 entry 12).…”

Section: Oxidation Reaction and Expected Mechanismmentioning

confidence: 99%

An Efficient Selective Oxidation of Alcohols with Zinc Zirconium Phosphate under Solvent‐free Conditions

Karimi

2015

J Chinese Chemical Soc

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Zinc zirconium phosphate (ZPZn) nanoparticles have been used as an efficient catalyst for the selective oxidation of a wide range of alcohols to their corresponding ketones or aldehydes using H 2 O 2 as an oxidizing agent without any organic solvent, phase transfer catalyst, or additive. The steric factors associated with the substrates had a significant influence on the reaction conditions. The results showed that this method can be applied for chemoselective oxidation of benzyl alcohols in the presence of aliphatic alcohols. The catalyst used in the current study was characterized by ICP-OES, XRD, N 2 adsorptiondesorption, NH 3 -TPD, Py-FTIR, SEM, and TEM. These analyses revealed that the interlayer distance in the catalyst increased from 7.5 to 8.7 Å when Zn 2+ was intercalated between the layers, whereas the crystallinity of the material was reduced. This nanocatalyst could also be recovered and reused at least seven times without any discernible decrease in its catalytic activity. This new method for the oxidation of alcohols has several key advantages, including mild and environmentally friendly reaction conditions, excellent yields and a facile work-up.

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Efficient Oxidation of Alcohols to Carbonyl Compounds by N,N‐Dichloro‐4‐Methylbenzenesulfonamide under Mild Conditions

Abstract: A number of aldehydes and ketones were prepared by oxidation of alcohol by N,N‐dichloro‐4‐methylbenzenesulfonamide under mild and neutral conditions in good to high yield in dichloromethane at room temperature.

Cited by 7 publications

References 22 publications

N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media

N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media

Tandem cyclocondensation-Knoevenagel–Michael reaction of phenyl hydrazine, acetoacetate derivatives and arylaldehydes

An Efficient Selective Oxidation of Alcohols with Zinc Zirconium Phosphate under Solvent‐free Conditions

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