Green High-Yielding One-Pot Approach to Biginelli Reaction under Catalyst-Free and Solvent-Free Ball Milling Conditions

M’hamed, Mohamed Ould; Alshammari, Abdulrahman G.; Lemine, O.M.

doi:10.3390/app6120431

Cited by 24 publications

(9 citation statements)

References 37 publications

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“…After work-up, the desired Biginelli compounds 12 – 15 were obtained in high yields without the need for any additional solvent (Table , entries 1–4). This SSD device allowed the synthesis of dihydropyrimidinones 12 – 14 via a multicomponent reaction, in yields similar to those previously reported, avoiding the use of solvents and decreasing energy consumption since the reaction is performed in very short reaction times.…”

Section: Resultssupporting

confidence: 57%

Advanced Mechanochemistry Device for Sustainable Synthetic Processes

et al. 2020

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Mechanochemistry is an alternative for sustainable solvent-free processes that has taken the big step to become, in the near future, a useful synthetic method for academia and the fine chemical industry. The apparatus available, based on ball milling systems possessing several optimizable variables, requires too many control and optimization experiments to ensure reproducibility, which has limited its widespread utilization so far. Herein, we describe the development of an automatic mechanochemical single-screw device consisting of an electrical motor, a drill, and a drill chamber. The applicability and versatility of the new device are demonstrated by the implementation of di- and multicomponent chemical reactions with high reproducibility, using mechanical action exclusively. As examples, chalcones, dihydropyrimidinones, dihydropyrimidinethiones, pyrazoline, and porphyrins, were synthesized with high yields. The unprecedented sustainability is demonstrated by comparison of EcoScale and E-factor values of these processes with those previously described in the literature.

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Section: Resultssupporting

confidence: 57%

Advanced Mechanochemistry Device for Sustainable Synthetic Processes

et al. 2020

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“…21 This equipment was successfully employed for di-and tri-component reactions to prepare several chalcones 78 (71% to 99% yields) (Scheme 18, Eqn 1), 3 with the custom custom-made SSD device (except for pyrazoline formation) afforded equal or superior yields than other mechanochemical-or solution-based methods. 102,103,104,105,106,107,108,109,110,100,111 For diphenyl chalcone 78, the E-Factor score was significantly better using the SSD device (0.17) than any green procedures (solvent-free procedure ground with mortar and pestle) previously reported (E-Factor: 0.39 to 0.51). 102,103,104 In contrast, the Ecoscale (74.5) was slightly worse than the solvent-free protocol (grinding with mortar and pestle) developed by Shan et al (Ecoscale score of 78).…”

Section: Scheme 17: Metalloporphyrin Synthesis By Mechanochemistrymentioning

confidence: 88%

Green metrics in Mechanochemistry

Fantozzi

Volle

Porcheddu

et al. 2022

Preprint

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The development of new green methodologies and their broader adoption for promoting sustainable development in chemistry laboratories and industry play a significant role in society, due to the economic importance of chemistry and its and widespread presence in everyday life. Therefore, a sustainable approach to chemistry contributes to the well-being of worldwide population and comply with the United Nations Sustainable Development Goals (UN SDGs) and the European Green Deal. The review highlights how mechanochemical methods in batch and in continuous are an eco-friendly approach for organic synthesis, with a lower environmental footprint in most cases, compared to solution-based procedures. The assessment is objectively based on the use of green metrics (e.g. atom and real atom economy, E-factor, Process Mass Intensity, Material Parameter Recovery, Eco-scale, Stoichiometric Factor, etc.) and indicators (e.g. DOZN tool and Life Cycle Assessment, LCA, studies) applied to organic transformations such as synthesis of amide bond, carbamates, heterocycles, Active Pharmaceutical Ingredients (APIs), porphyrins, Porous Organic Polymers (POPs), metal- or acid-catalysed processes, multicomponent and condensation reactions, rearrangements, etc. The generalized absence of bulk solvents, the precise control over the stoichiometry (i.e., using agents in a stoichiometrically rather than in excess), and the more selective reactions enabling simplified work-up procedures are the distinctive factors marking the superiority of mechanochemical processes over solution-based chemistry.

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“…As temperature increased Dihydropyrimidones are synthesized under solvent -free and milling conditions. [46] The reaction performed using 1 (0.02 mol), 3 (0.02 mol) and 5 (0.02 mol) was placed into tempered steel vials with 47.36 g of tempered steel balls (22 balls of in 10 mm diameter). The different balls to reagents weight ratios (BRR) were investigated.…”

Section: Homogeneous Catalystmentioning

confidence: 99%

Recent Advances in Homogeneous and Heterogeneous Catalyst in Biginelli Reaction from 2015‐19: A Concise Review

Chopda

Dave

2020

ChemistrySelect

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In the chemistry world, the year 1891 was considered as milestone year for the discovery of new type of heterocyclic compounds by Pietro Biginelli. The Biginelli protocol provides 3,4-dihydropyrimidin-2(1H)-ones/thiones in the presence of Bronsted acids and Lewis acids. Multifunctional Dihydropyrimidones (DHPMs) are displayed wide medicinal properties. Several of homogeneous and heterogeneous catalysts have been reported to improve the yield of product. This review includes the progress of ionic liquids, combination of ionic liquids with homogeneous & heterogeneous catalyst, homogeneous, heterogeneous and asymmetric catalyst took place in last five year (2015-2019) for Biginelli reaction. Most of catalysts showed good catalytic activity (more than 80 %) towards the synthesis of Biginelli adducts. [a] Mr. Scheme 1. Biginelli reaction. ChemistrySelect Reviews Figure 1. Structure of ionic liquids. Scheme 2. Synthesis of DHPMS by [C 3 SO 3 HDoim]HSO 4. Scheme 3. Synthesis of 7 by L-proline nitrate.ChemistrySelect Reviews

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Green High-Yielding One-Pot Approach to Biginelli Reaction under Catalyst-Free and Solvent-Free Ball Milling Conditions

Cited by 24 publications

References 37 publications

Advanced Mechanochemistry Device for Sustainable Synthetic Processes

Advanced Mechanochemistry Device for Sustainable Synthetic Processes

Green metrics in Mechanochemistry

Recent Advances in Homogeneous and Heterogeneous Catalyst in Biginelli Reaction from 2015‐19: A Concise Review

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