An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives

Mocci, Rita; Luca, Lidia De; Delogu, Francesco; Porcheddu, Andrea

doi:10.1002/adsc.201600350

Cited by 27 publications

(17 citation statements)

References 101 publications

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“…As a representative and successful example of this approach, Teriflunomide, an API indicated in the treatment of multiple sclerosis, 13 was isolated in 81% overall yield (Scheme 1). This approach was further applied by various research groups to the synthesis of a large array of benzoylhydrazides, 14 hydroxamic acids, 15 and glycoamides, 16 with strong emphasis on the efficiency, user-friendliness, and low environmental impact of the method. Of note, the capacity of this strategy to avoid traditional solubility and purification concerns was highlighted.…”

Section: ■ Discussionmentioning

confidence: 99%

1,1′-Carbonyldiimidazole and Mechanochemistry: A Shining Green Combination

Métro

Martinez

Lamaty

2017

ACS Sustainable Chem. Eng.

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The application of mechanical forces to enable a chemical reaction, also known as mechanochemistry, is actually experiencing an impressive renewal of interest among the chemists community. One major advantage of this approach in organic synthesis lies in the possibility to run essentially solvent-free reactions. In recent years, some research groups have combined these types of solvent-free processes with the use of an eco-friendly reagent: 1,1′-carbonyldiimidazole (CDI). Thus, a wide range of molecules, including carboxylic acids, amines, and alcohols, could react efficiently with CDI under ball-milling conditions. By providing a vast array of products (amides, carboxylic acids, esters, ureas, hydantoins, etc.) in an efficient, fast, user-friendly, and green manner, this approach presents all the prerequisites to soon become a first choice methodology for all organic chemists. The reasons for the past and future successes of this combination are summarized, analyzed, and discussed herein.

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Section: ■ Discussionmentioning

confidence: 99%

1,1′-Carbonyldiimidazole and Mechanochemistry: A Shining Green Combination

Métro

Martinez

Lamaty

2017

ACS Sustainable Chem. Eng.

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“…Furthermore, energy dispersive xray spectroscopy (EDX) analysis with a scanning electron microscope (SEM) of pristine and milled benzohydroxamic acid samples confirmed the presence of iron and chromium in the latter sample, both of which are contained within the steel jars that were used ( Figure 1). It is interesting to note that Mocci et al [26] do not mention leaching of iron during their hydroxamic acid mechanochemical synthesis. We can only speculate that ageing of the steel-constructed jars may be the cause of our observation of leaching and we advise when using mechanochemistry to be aware of this issue with steel grinding jars, as leaching of iron or chromium may not only interfere with the reactants but also catalyse reactions [27,28] both of which may lead to inaccurate results.…”

Section: Resultsmentioning

confidence: 99%

Mechanochemical Synthesis of N‐Aryl Amides from O‐Protected Hydroxamic Acids

et al. 2020

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Two robust and efficient mechanochemical protocols for the synthesis of an array of N‐arylamides have been developed. This was achieved by a C−N cross‐coupling between O‐pivaloyl hydroxamic acids and aryl iodides or aryl boronic acids, in the presence of a stoichiometric amount of a copper mediator. The effectiveness of this method is highlighted by the high‐yielding (up to 94 %), scalable (up to 8 mmol), and rapid (20 minutes) synthesis of N‐aryl amides (15 examples), using a variety of deactivated and sterically encumbered substrates, whilst employing mild conditions and in the absence of solvents. In addition, it was determined that whilst the O‐pivaloyl hydroxamic acid precursors can be synthesised mechanochemically, iron contamination originating from the steel jars was found to occur which can hinder the efficacy of this process. Furthermore, 3D printing was used to produce custom milling jars that could successfully accommodate a scaled‐up version of the two protocols.

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“…This procedure does not require any aqueous workup and it is potentially scalable, economical and environmentally friendly. N -sulfohydroxamic acids are isolated at high yield and purity after a simple filtration [ 68 , 69 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Nitric Oxide Donors Derived from Piloty’s Acid and Study of Their Effects on Dopamine Secretion from PC12 Cells

et al. 2017

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This study investigated the mechanisms and kinetics of nitric oxide (NO) generation by derivatives of Piloty’s acid (NO-donors) under physiological conditions. In order to qualitatively and quantitatively measure NO release, electron paramagnetic resonance (EPR) was carried out with NO spin trapping. In addition, voltammetric techniques, including cyclic voltammetry and constant potential amperometry, were used to confirm NO release from Piloty’s acid and its derivatives. The resulting data showed that Piloty’s acid derivatives are able to release NO under physiological conditions. In particular, electron-withdrawing substituents favoured NO generation, while electron-donor groups reduced NO generation. In vitro microdialysis, performed on PC12 cell cultures, was used to evaluate the dynamical secretion of dopamine induced by the Piloty’s acid derivatives. Although all the studied molecules were able to induce DA secretion from PC12, only those with a slow release of NO have not determined an autoxidation of DA itself. These results confirm that the time-course of NO-donors decomposition and the amount of NO released play a key role in dopamine secretion and auto-oxidation. This information could drive the synthesis or the selection of compounds to use as potential drugs for the therapy of Parkinson’s disease (PD).

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An Environmentally Sustainable Mechanochemical Route to Hydroxamic Acid Derivatives

Cited by 27 publications

References 101 publications

1,1′-Carbonyldiimidazole and Mechanochemistry: A Shining Green Combination

1,1′-Carbonyldiimidazole and Mechanochemistry: A Shining Green Combination

Mechanochemical Synthesis of N‐Aryl Amides from O‐Protected Hydroxamic Acids

Synthesis of Nitric Oxide Donors Derived from Piloty’s Acid and Study of Their Effects on Dopamine Secretion from PC12 Cells

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