Efficient and Facile Method for the Nitration of Aromatic Compounds by Nitric Acid in Micellar Media

Sana, Sariah; Tasneem,; Ali, M. M.; Rajanna, K. C.; Saiprakash, P. K.

doi:10.1080/00397910802711318

Cited by 24 publications

(12 citation statements)

References 2 publications

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“…DHP 6 was synthesized by starting from the well‐known 2,7‐di‐ tert ‐butyl‐DHP 7 in 14 % yield over five steps. After nitration with Cu(NO 3 ) 2 in the 4‐position and subsequent reduction with Zn in the presence of acetic anhydride, a second nitration step provided 4‐amido‐9‐nitro‐DHP 10 . Deprotection using 1,8‐diazabicyclo[5.4.0]undec‐7‐ene (DBU) gave the free amine 11 , which can be methylated with MeI and K 3 PO 4 (Scheme ).…”

Section: Figurementioning

confidence: 99%

Dihydropyrene as an Aromaticity Probe for Partially Quinoid Push–Pull Systems

2017

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Although aromaticity is a key concept in chemistry that is frequently used to explain the structure and reactivity of organic compounds, it remains challenging to actually measure this property. Proper probes allow for an experimental quantification of aromaticity using nuclear magnetic resonance (NMR) spectroscopy and in this study 15,16‐dimethyl‐15,16‐dihydropyrene (DHP) is demonstrated to be particularly well suited for this purpose. DHP has two internal methyl groups, which are positioned within the π cloud of this bridged, planar, and rigid [14]annulene, and are therefore shifted to higher field in proton NMR spectra owing to ring‐current effects. A specific DHP derivative bearing strongly electron‐donating dimethylamino and strongly electron‐accepting nitro groups in a relative pseudo‐para orientation has been synthesized and characterized with respect to its quinoid character. Solvatochromism as well as a reduced ring current show that the partial quinoid character in this push–pull DHP derivative is about 12 %. This study extends the scope of DHP as an aromaticity probe and aids in the better understanding of the phenomenon of aromaticity.

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Section: Figurementioning

confidence: 99%

Dihydropyrene as an Aromaticity Probe for Partially Quinoid Push–Pull Systems

2017

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“…Mukherjee and Boshaff [18] explored that nitroimidazoles could be effectively used for the treatment of TB. During the past two decades our research group is also actively involved to achieve nitration using eco-friendly reagents and catalysts [19][20][21][22][23][24][25][26][27][28][29].…”

Section: Introductionmentioning

confidence: 99%

Trichloroisocyanuric acid and NaNO2 mediated nitration of indoles under acid-free and Vilsmeier–Haack conditions: synthesis and kinetic study

et al. 2019

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This study deals with the synthetic and kinetic aspects of trichloroisocyanuric acid (TCCA) and NaNO 2 mediated nitration of indoles in aqueous acetonitrile media under acid-free and Vilsmeier-Haack conditions (using N,N′-dimethyl amides) conditions. Nitration of indoles revealed second order kinetics, with a first order dependence on [indole] and [nitrating agent] ([TCCA]/[NaNO 2 ], [(TCCA-DMF)]/[NaNO 2 ] or [(TCCA-DMA)]/[NaNO 2 ], in which [NaNO 2 ] far excess over other reagents). Reactions followed overall second order kinetics with first order in [reagent] and [indole] under the experimental conditions. Isokinetic temperature (β) values were obtained from Leffler's equation for different kinetic protocols (β = 303 K (TCCA-NaNO 2 ); 303 K (TCCA-DMF)/NaNO 2 ; and 244 K (TCCA-DMA)/NaNO 2 ). These values are the experimental temperature range (303-323 K) indicating that the entropy factors are probably more important in controlling the reaction.

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“…Owing to the widespread presence of nitro compounds in pharmaceuticals, natural products, organic intermediates, catalysts, and high energy density materials, the application of this process has been exceptionally broad. However, based on the principles of green chemistry, most industrial nitration processes are less environmentally‐friendly because they use nitric acid, nitrates, and nitrous esters as nitrating agents . For the time being, the greenest reagents for nitration are nitrogen oxides (N x O y ), especially nitrogen dioxide (NO 2 ), because they are able to maximize the utilization of nitrogen atoms and oxygen atoms to prepare nitro compounds …”

Section: Introductionmentioning

confidence: 99%

The application of nitrogen oxides in industrial preparations of nitro compounds

2018

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Nitrogen oxides of atomic economy are promising nitrating agents instead of common nitric and sulphuric acids in the industrial preparations of nitro compounds. This review provides recent developments of nitration using nitrogen oxides found in applied research. Novel nitration involving three classes of nitrogen oxides is described for the synthesis of organic intermediates, medicinally relevant compounds, natural products, high energy density materials, and some catalytic materials.

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Efficient and Facile Method for the Nitration of Aromatic Compounds by Nitric Acid in Micellar Media

Cited by 24 publications

References 2 publications

Dihydropyrene as an Aromaticity Probe for Partially Quinoid Push–Pull Systems

Dihydropyrene as an Aromaticity Probe for Partially Quinoid Push–Pull Systems

Trichloroisocyanuric acid and NaNO2 mediated nitration of indoles under acid-free and Vilsmeier–Haack conditions: synthesis and kinetic study

The application of nitrogen oxides in industrial preparations of nitro compounds

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