<i>p</i>‐Toluenesulfonylmethyl Isocyanide (TosMIC) and Indium Manifold Strategy to Access β‐Keto‐(<i>E</i>)‐enamino Esters from 1,3‐Dicarbonyl Compounds

Krishna, Palakodety Radha; Sekhar, Empati Raja

doi:10.1002/adsc.200800368

Cited by 13 publications

(3 citation statements)

References 47 publications

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“…[14] The most straightforward method for synthesizing β-ketoenamines is the direct condensation of 1, 3-dicarbonyl compounds with amines in an aromatic solvent, [15,16] with improved methods developed. [17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] In this paper, we present a gentle and effective method for synthesizing β-ketoenamines in DI water as a solvent, while adhering to the principles of green chemistry (Figure 2, Table 1). The key advantages of this methodology are as follows: (a) the reaction is simple to carry out; (b) it yields moderate to good results; (c) the process works for a wide range of aromatic primary amines; and (d) there is no need to purify the β-ketoenamines (Figure 2).…”

Section: Introductionmentioning

confidence: 99%

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Taguchi method and neural network for efficientβ‐ketoenaminesynthesis in deionized water

Ghabi,

Landolsi,

Echouchene

et al. 2024

Can J Chem Eng

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The optimization of performance parameters, in particular the yield of the synthesis reaction of β‐enaminones in demineralized water, is crucial to improve their efficiency and accuracy. In this report, we investigate the optimization of the synthesis of β‐ketoenamines in deionized water by controlling several parameters such as reaction time, temperature, amine equivalent, acid percentage, and stirring rate. An orthogonal L16 (45) network was created using Taguchi's approach, allowing for the best possible parameters. To forecast the contribution of each parameter, analysis of variance (ANOVA) techniques are also used. Multiple linear and nonlinear regression (MLR, MNLR) and multilayer perception artificial neural network (MLP‐ANN) predictive models were developed. Analysis of the results led to optimized design parameters, with time = 6 h, temperature = 25°C, amine equivalent = 1.5, acid percentage = 20%, and stirring rate = 1000 rpm, leading to a maximum yield of 63%. ANOVA analysis revealed that temperature, stirring rate, acid percentage, and time are the parameters with the greatest influence. The least sensitive parameter is the amine equivalent. The two main interactions are temperature * acid % and amine equivalent * rpm. The MLP‐ANN predictions are in good agreement with the experimental values, resulting in a higher R2 compared to the quadratic regression model and the MLR model. By using molecular docking studies, the produced compounds' biological activity was investigated. Some of the synthesized compounds appear to be interesting and could be used for therapeutic applications. The results of this study give us insight into the gentle, cost‐effective, and biologically active synthesis of β‐enaminones in deionized water.

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Section: Introductionmentioning

confidence: 99%

“…The most straightforward method for synthesizing β‐ketoenamines is the direct condensation of 1, 3‐dicarbonyl compounds with amines in an aromatic solvent, [ 15,16 ] with improved methods developed. [ 17–31 ]…”

Section: Introductionmentioning

confidence: 99%

Taguchi method and neural network for efficientβ‐ketoenaminesynthesis in deionized water

Ghabi,

Landolsi,

Echouchene

et al. 2024

Can J Chem Eng

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“…One of the most straightforward methods is condensation between 1,3-dicarbonyls and amines under reflux conditions [20]. Other improved methods for this amination reaction were successively developed [21,22,23,24,25,26,27,28,29,30,31,32,33,34]. However, in these procedures, the long reaction time, high reaction temperatures, and high catalyst loadings required could limit their further applications in organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Efficient Synthesis of β-Enaminones and β-Enaminoesters Catalyzed by Gold (I)/Silver (I) under Solvent-Free Conditions

Zhang

Abdukader

et al. 2012

Molecules

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Copper‐Catalyzed N‐Aryl‐β‐enaminonitrile Synthesis Utilizing Isocyanides as the Nitrogen Source

Kim

Hong

2015

Adv Synth Catal

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An ovel synthetic protocol for N-aryl-b-enaminonitriles,w hich are useful building blocks for heterocycle synthesis, was developed using isocyanides as the nitrogen source.U sing copper-catalyzed one-stepr eactions between isocyanides and benzyl cyanidesu nder mild conditions,d iverse N-aryl-b-enaminonitriles could be synthesizedi ne xcellent yields and with high atom-efficiency. N-Alkyl-b-enaminonitriles were also synthesizedi ng ood yields. Am echanism involving an imidoyl-copper intermediate was proposedb ased on mechanistic studies and previous reports. In addition,w ed emonstrated that as ynthesized N-aryl-b-enaminonitrile could be utilized for the synthesiso fab -keto nitrile compound and3 -aminopyrazole.

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p‐Toluenesulfonylmethyl Isocyanide (TosMIC) and Indium Manifold Strategy to Access β‐Keto‐(E)‐enamino Esters from 1,3‐Dicarbonyl Compounds

Cited by 13 publications

References 47 publications

Taguchi method and neural network for efficientβ‐ketoenaminesynthesis in deionized water

Taguchi method and neural network for efficientβ‐ketoenaminesynthesis in deionized water

Efficient Synthesis of β-Enaminones and β-Enaminoesters Catalyzed by Gold (I)/Silver (I) under Solvent-Free Conditions

Copper‐Catalyzed N‐Aryl‐β‐enaminonitrile Synthesis Utilizing Isocyanides as the Nitrogen Source

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