Green one-pot multicomponent synthesis of pyrrolidinones using planetary ball milling process under solvent-free conditions

Khaligh, Nader Ghaffari; Mihankhah, Taraneh; Johan, Mohd Rafie

doi:10.1080/00397911.2019.1601225

Cited by 14 publications

(11 citation statements)

References 19 publications

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“…As expected, higher yield of cyclization products was reached upon employing ortho-para aldehyde derivatives particularly those containing electron donating groups (Table 3, entries 1-14) due to activation of the carbonyl by electronic resonance effect of the ortho-para electron donating groups. Similar observation was reported for the milling-ball mechanochemical process [14]. However, using benzylamine in the same process led to low yield of the product (Table 3, entry 14).…”

Section: Resultssupporting

confidence: 84%

“…However, using benzylamine in the same process led to low yield of the product (Table 3, entry 14). All synthesized compounds had spectral and physical characteristics consistent with those reported earlier [14,15].…”

Section: Resultssupporting

confidence: 84%

“…Poor solubility and multiple reactive sites of 1a could cause multiple side-reactions and result in moderate yield of products. For this reason we switched from nucleophilic diethyl oxaloacetate (1a) to the more reactive diethylacetylene dicarboxylate (1b) which was known as a reagent in cyclization of pyrrolidinone under various reaction protocols including planetary ball-mill process [14]. Unfortunately, 1b still led to poor yield of cyclization products (Table 1, entries 12-14).…”

Section: Resultsmentioning

confidence: 99%

“…Accordingly, combination of aniline with citric acid catalyst [14] gave the title compound 2b in high yield of 89%. Similarly the switch from aldehyde to 4-chlorobenzaldehyde led to 2b in 88% yield (Table 1, entries 15,16).…”

Section: Resultsmentioning

confidence: 99%

“…Simple separation and purification of products without use of column chromatography with minimum solvents used are attractive points of this protocol. Similar approach to the title compounds by means of mechano-chemical process involving complicated planetary ball milling equipment and expensive binuclear Brønsted acid ionic liquids catalyst had been reported earlier [14]. The same researchers later presented synthesis of the same compounds via MW irradiation approach [15].…”

Section: Introductionmentioning

confidence: 97%

See 4 more Smart Citations

Synthesis of Ethyl 3-Methyl-4,5-dioxo-1,2-diphenylpyrrolidine-3-carboxylate Analogues Using Green and Expeditious Grinding Method

et al. 2021

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A specific efficient method of synthesis of biologically active analogues of the title compound from acetylene dicarboxylate, aniline and various aromatic aldehydes catalyzed by citric acid by one-pot mortar-pestle grinding is described. The short time synthesis is characterized by high yields and comparable with the similar mechano-chemical process of planetary ball-milling. Easy isolation of the products without involving separation methods makes this green synthesis to be cost-efficient.

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Section: Resultssupporting

confidence: 84%

Section: Resultssupporting

confidence: 84%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 97%

See 3 more Smart Citations

Synthesis of Ethyl 3-Methyl-4,5-dioxo-1,2-diphenylpyrrolidine-3-carboxylate Analogues Using Green and Expeditious Grinding Method

et al. 2021

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Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

2022

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Dialkyl acetylenedicarboxylates (DAAD) are the class of acetylenic compounds that are broadly used in organic synthesis in a noticeable quantity. Their wide application has made them an important moiety in heterocyclic compounds and drug discovery programs. Dialkyl acetylenedicarboxylate is a di-ester in which the ester groups are conjugated with a carbon-carbon triple bond. As such, the molecule is very electrophilic, and is broadly used as a dienophile in various cycloaddition reactions, for example the Diels-Alder reaction. In addition, it is a strong Michael acceptor. Due the importance of dialkyl acetylenedicarboxylate in organic synthesis, we are trying to show the applications of this compound in the synthesis of different heterocycles using multicomponent reactions. In this review, we show recent advances (2016)(2017)(2018)(2019)(2020)(2021)(2022) for the synthesis of various heterocycles that have different ring sizes (five, six and seven membered, Spiro and fused heterocycles), using DAAD via multicomponent reactions.

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Green one-pot multicomponent synthesis of pyrrolidinones using planetary ball milling process under solvent-free conditions

Cited by 14 publications

References 19 publications

Synthesis of Ethyl 3-Methyl-4,5-dioxo-1,2-diphenylpyrrolidine-3-carboxylate Analogues Using Green and Expeditious Grinding Method

Synthesis of Ethyl 3-Methyl-4,5-dioxo-1,2-diphenylpyrrolidine-3-carboxylate Analogues Using Green and Expeditious Grinding Method

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

Use of Dialkyl Acetylenedicarboxylates in the Multicomponent Synthesis of Heterocyclic Structures

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