An efficient solvent-free synthesis of 3-acetyl-4-arylquinoline-based enaminones and its derivatives using DMFDMA reagent

Kumar, L. Jyothish; Vijayakumar, V.

doi:10.1007/s11696-017-0375-5

Cited by 7 publications

(6 citation statements)

References 27 publications

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“…Various active methylenes were also attempted, taking a shorter reaction time than methyl ketones. Active methylenes like benzyl cyanide, ethyl cyanoacetate, and β-ketoester ethyl acetoacetate reaction completed in reasonable time with excellent yield (Table 4 entries [22][23][24]. While diester, diethyl malonate as an exception took a longer reaction time (Table 4 entry 25).…”

Section: Chemistryselectmentioning

confidence: 99%

“…The most common approach to preparing enaminone was from the mixture of acetophenone and DMF-DMA reflux in toluene. [24] In a mission to develop greener synthetic methods, our research group synthesized eco-friendly, inexpensive catalyst, Sulfated polyborate from boric acid, a readily available, economical, non-toxic material, and applied to various organic transformations. [25] We herein report the application of sulfated polyborate and other Brönsted acids as catalysts to synthesize enaminones and enamines of methyl ketones and active methylenes (Scheme 1b).…”

Section: Introductionmentioning

confidence: 99%

“…10,24, 25) were isolated by water quenching and ethyl acetate extraction after excess DMF-DMA and methanol were removed under a vacuum. During the aqueous quenching, the presence of the acid catalyst led to the formation of DMF from the traces of DMF-DMA.…”

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confidence: 99%

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Sulfated Polyborate Catalyzed Improved Synthesis of Enamines and Enaminones Based Intermediates of Imatinib, Nilotinib and Ocinaplon**

2023

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An activation of methyl ketones or active methylenes and N, Ndimethylformamide dimethyl acetal at 110 °C by sulfated polyborate under solvent-free conditions has been developed for enamines and enaminones synthesis. Selected Brønsted acid, optimized reaction conditions, and easy separation method lead to 82-97 % yield, making this process costeffective and eco-friendly. We chose boric acid for scale-up activity in the interest of readers and industries. The optimized reaction condition was applied to demonstrate a 10 gram scale for the intermediate of Imatinib and Nilotinib with an 80 % from 3-acetylpyridine. This method is extendable to produce Ocinaplon intermediate with 80.6 % yield using 4-acetyl pyridine as starting material.

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Section: Chemistryselectmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Sulfated Polyborate Catalyzed Improved Synthesis of Enamines and Enaminones Based Intermediates of Imatinib, Nilotinib and Ocinaplon**

2023

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“…In addition, it is well known that enaminone 14 is the key precursor for the synthesis of many different heterocycles, such as pyrazole, isoxazole, pyrimidine, and pyridine …”

Section: Methylation By Using Conventional Reagentsmentioning

confidence: 99%

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Chen

2018

Chemistry A European J

201

121

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Methylation is a well‐known structural modification in organic and medicinal chemistry. This review summarizes recent advances in methylation by categorizing specific methylation reagents. The challenges of mono N‐methylation of aliphatic amines and N‐methylation of peptides are discussed. This review will be useful for chemists wanting to select the appropriate reagents for methylation chemistry. Based on the large diversity of methylation reagents and their wide scope, this review also broadens perspectives on which strategies to select for utilizing a particular methylation, resulting in an increased flexibility in synthetic route planning.

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“…18,19 The most common approach to preparing enaminone was from the mixture of acetophenone and DMF-DMA re ux in toluene. 21 There was a broad scope to develop methods that circumvent isolation problems and broaden substrate choices.…”

Section: Introductionmentioning

confidence: 99%

Sulfated polyborate catalyzed enamines, enaminones synthesis via Methyl Ketones, Active Methylenes, and DMF-DMA activation: Application to Imatinib, Nilotinib intermediates †

Bandivadekar

Gavali

Chaturbhuj

2022

Preprint

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An activation of methyl ketones or active methylenes and N,N-dimethylformamide dimethyl acetal (DMF-DMA) at 110 °C by sulfated polyborate under solvent-free conditions has been developed for enamines and enaminones synthesis. Selected Brønsted acid, optimized reaction conditions, and easy separation method lead to 82-97% yield, making this process cost-effective and eco-friendly. We chose boric acid for scale-up activity in the interest of readers and industries. The optimized reaction condition was applied to demonstrate a 10 gm scale-up for intermediate of Imatinib and Nilotinib with 80% yield from 3-acetylpyridine. This method is extendable to produce Ocinaplon intermediate using 4-acetyl pyridine as starting material.

show abstract

An efficient solvent-free synthesis of 3-acetyl-4-arylquinoline-based enaminones and its derivatives using DMFDMA reagent

Cited by 7 publications

References 27 publications

Sulfated Polyborate Catalyzed Improved Synthesis of Enamines and Enaminones Based Intermediates of Imatinib, Nilotinib and Ocinaplon**

Sulfated Polyborate Catalyzed Improved Synthesis of Enamines and Enaminones Based Intermediates of Imatinib, Nilotinib and Ocinaplon**

Recent Advances in Methylation: A Guide for Selecting Methylation Reagents

Sulfated polyborate catalyzed enamines, enaminones synthesis via Methyl Ketones, Active Methylenes, and DMF-DMA activation: Application to Imatinib, Nilotinib intermediates †

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