Glucose promoted facile reduction of azides to amines under aqueous alkaline conditions

Chandna, Nisha; Kaur, Fatehjeet; Kumar, Shobhna; Jain, Nidhi

doi:10.1039/c7gc01593c

Cited by 18 publications

(14 citation statements)

References 24 publications

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“…To the best of our knowledge, there is only one case of reduction reported in a low melting mixture: the catalytic hydrogenation of methyl α‐cinnamate run in the melt citric acid‐dimethyl urea using the Wilkinson's catalyst (15 mol %) (90 °C, 1 atm H 2 ) A survey of conditions was undertaken to optimise this step in the above DES. A complex mixture always formed when azide 2a was treated at r.t. with Zn/ammonium formate, Zn/HCl, Zn/NH 4 Cl, Ph 3 P, or d ‐glucose/KOH as reducing agents (Table , entries 1–5). Pleasingly, when SnCl 2 · 2H 2 O was alternatively used the reduction of the azide moiety to the corresponding α‐amino ketone this time took place, but the latter spontaneously underwent dimerisation/cyclisation in the same eutectic mixture leading to the isolation of 2,5‐diphenylpyrazine 4a as the sole product in 48 % yield (Table , entry 6).…”

Section: Resultsmentioning

confidence: 99%

Streamlined Routes to Phenacyl Azides and 2,5‐Diarylpyrazines Enabled by Deep Eutectic Solvents

et al. 2019

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A Deep Eutectic Solvent like choline chloride/glycerol (1:2 mol mol–1) proved to be an effective, sustainable reaction medium to easily synthesize both phenacyl azides and symmetrical 2,5‐diarylpyrazines of interest in pharmacology and in coordination chemistry. Notable features of our report include: (i) nucleophilic substitution reactions of α‐halo carbonyl compounds to the corresponding phenacyl azides compatible with the eutectic mixture, (ii) the reduction of phenacyl azides to α‐amino carbonyl compounds, which undergo spontaneous dimerisation/cyclisation/aromatisation in the same eutectic mixture to provide valuable pyrazines. Telescoped, one‐pot, two‐steps stoichiometric/catalytic processes have also been successfully developed to furnish 2,5‐diarylpyrazines in up to 95 % yield.

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Section: Resultsmentioning

confidence: 99%

Streamlined Routes to Phenacyl Azides and 2,5‐Diarylpyrazines Enabled by Deep Eutectic Solvents

et al. 2019

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“…[ 1–3 ] Moreover, they have been employed as abundant renewable carbon sources in the preparation of N‐heterocycles [ 4,5 ] and as hydrogen sources in mild and eco‐friendly reduction processes. [ 6–8 ] In particular, d ‐glucose is an extremely abundant natural product which can be easily obtained from lignocellulosic biomass (e.g. wood) via enzymatic treatment or acid hydrolysis.…”

Section: Figurementioning

confidence: 99%

“…Under avoidance of strong bases such as potassium hydroxide or sodium hydroxide which were regularly applied in reductions with glucose, [ 6,12,25 ] an environmentally benign and inexpensive base, potassium carbonate, [ 26 ] was chosen in conjunction with an aqueous glucose solution (Table 1). Initially, by setting the temperature to 100 °C and the solvent volume to 0.8 mL with 0.8 mmol (4 equiv.)…”

Section: Figurementioning

confidence: 99%

Glucose as an Eco‐Friendly Reductant in a One‐Pot Synthesis of 2,3‐Dihydroquinazolin‐4(1H)‐ones

et al. 2020

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Carbohydrates such as glucose are an abundant renewable resource that can be employed in synthetic processes as a source of carbon and/or hydrogen to yield products of high economical and biological impact. Herein, we report a versatile and environmentally friendly protocol for the one‐pot synthesis of 2,3‐dihydroquinazolin‐4(1H)‐ones, a privileged scaffold in medicinal chemistry, based on the use of glucose as an eco‐friendly reductant in alkaline aqueous medium. This method can be viewed as a blueprint for the development of further one‐pot sequences involving glucose as a reductant.

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“…Reducing sugars nowadays are viewed as green, reducing agents for reduction of nitro, azide, nitroso etc. functionality in the synthesis of compounds [4] .…”

Section: Introductionmentioning

confidence: 99%

A novel spot test for Differentiating between reducing and nonreducing sugar

2020

jcbsc

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The carbohydrates alternatively called, "saccharides," and "sugars" are classified as reducing and nonreducing sugars. Reducing sugars like glucose, mannose and fructose derived from natural resources, can reduce varied functional groups including nitro, nitroso, azide etc., thereby, viewed as green reducing agents in synthetic chemistry. Nonreducing sugars in plants like sucrose and trehalose play a significant role in carbohydrates storage, carbon transport, photosynthesis, and protect against stress. The distinction between reducing and nonreducing sugar is an integral part of carbohydrate qualitative and quantitative analysis in the research field of plant food science. The most common conventional reagents known for the differentiation between reducing and nonreducing sugars include Tollen's, Fehling's, Benedicts, Barfoed's etc. However, these reagents consist of nitrate and sulphate of heavy metals like silver and copper. Copper sulphate in Fehling's and Benedict's reagent drain into the water bodies and are responsible for Wilson's disease. Tollen's reagent is expensive and requires excessive use of hazardous liquid ammonia. Use of Potassium ferrocyanide required in Hagedorn-Jenson Method is associated with renal effect and releases poisonous hydrogen cyanide gas on heating. In present work, we newly introduced a more convenient spot test, which utilizes inexpensive and readily available m-dinitrobenzene (MDN) reagent. The reagent can be easily prepared and distinguish sugars within 60 seconds as compared to the mentioned conventional reagents that take a longer time of differentiation and tedious in their preparation. Therefore, MDN may be a promising reagent for a spot test of sugars. The test is beneficial to both chemist and biochemist.

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Glucose promoted facile reduction of azides to amines under aqueous alkaline conditions

Abstract: A quick and efficient method for the reduction of azides to amines in water using d-glucose and KOH as green reagents is reported.

Cited by 18 publications

References 24 publications

Streamlined Routes to Phenacyl Azides and 2,5‐Diarylpyrazines Enabled by Deep Eutectic Solvents

Streamlined Routes to Phenacyl Azides and 2,5‐Diarylpyrazines Enabled by Deep Eutectic Solvents

Glucose as an Eco‐Friendly Reductant in a One‐Pot Synthesis of 2,3‐Dihydroquinazolin‐4(1H)‐ones

A novel spot test for Differentiating between reducing and nonreducing sugar

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