Aza-Michael Addition of Imidazole Analogues

Gmach, Joanna; Joachimiak, Łukasz; Błażewska, K. M.

doi:10.1055/s-0035-1560451

Cited by 33 publications

(8 citation statements)

References 86 publications

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“…However, they are inert under mild conditions (DCM, rt, 24 h) in the reaction with alkenes bearing one of the most electron‐withdrawing functions, namely the nitro group [14] . Many examples of imidazole addition to various Michael acceptors have been analyzed in comprehensive review by Prof. Błażewska and co‐authors in 2016 [9] and more recently by Mohapatra and co‐authors [10] . Here, only some important examples or ones not mentioned in these reviews are shown.…”

Section: Pyrazoles Imidazoles Triazoles and Tetrazolesmentioning

confidence: 99%

“…The asymmetric aza‐Michael addition of nucleophiles bearing various azole moieties has been discussed in mini‐review published in 2012 [8] . Two reviews describe the conjugate nucleophilic addition of imidazoles as Michael donors [9,10] . Finally, reactions of aromatic aza‐heterocycles, as well as amides and carbamates with various Michael acceptors have been presented in my previous review [11] .…”

Section: Introductionmentioning

confidence: 99%

“…[8] Two reviews describe the conjugate nucleophilic addition of imidazoles as Michael donors. [9,10] Finally, reactions of aromatic azaheterocycles, as well as amides and carbamates with various Michael acceptors have been presented in my previous review. [11] Despite these publications, a review dealing with general aspects of the use of various weak nucleophiles in the aza-Michael reaction has not been considered anywhere.…”

Section: Introductionmentioning

confidence: 99%

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Weak Nucleophiles in the Aza‐Michael Reaction

Rulev

2023

Adv Synth Catal

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The 1,4‐conjugated addition of nitrogen centered nucleophiles to electron‐deficient alkenes is one of the most significant and widely used reactions in modern synthetic organic chemistry. To date, various protocols for the aza‐Michael reaction have been developed. However, these reports mainly focus on the use of strong Michael donors. In recent years, the conjugate addition of weak nitrogen nucleophiles to various Michael acceptors gained increasing popularity. Impressive progress in this area has been achieved by the use of more efficient catalyst systems. This review aims to provide a critical analysis of the results obtained in reactions of weak nucleophiles (azoles, pyrroles, indoles, carbamates, purines, amides, hydrazides, uraciles etc) with electron‐deficient alkenes which were reported over the past twelve years.

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Section: Pyrazoles Imidazoles Triazoles and Tetrazolesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Weak Nucleophiles in the Aza‐Michael Reaction

Rulev

2023

Adv Synth Catal

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“…Various researchers have reported about the green synthesis of CuO nanoparticles from various plant extract such as Aloe vera, , Terminalia phanerophlebia, Gloriosa superba, Psidium guajava, Solanum nigrum, Abutilon indicum, Lantana camara, and Malva sylvestris . This phytomediated method using different plant extracts is considered an innovative, low-cost, and modest approach for synthesizing CuO nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

Ocimum sanctum Leaf Extract-Assisted Green Synthesis of Pd-Doped CuO Nanoparticles for Highly Sensitive and Selective NO₂ Gas Sensors

et al. 2023

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In view of facile, cost-effective, and environmentally friendly synthetic methods, palladium-doped copper oxide (Pd-CuO) nanoparticles have been synthesized from Ocimum sanctum (commonly known as "Tulsi") phytoextract for gas-sensing applications. The structural, morphological, and compositional properties of Pd-doped CuO nanoparticles were studied using various techniques such as XRD, FESEM, XPS, and EDX. The characterization results confirmed the doping of Pd on CuO nanoparticles, and Pd-CuO nanostructures appear as nanoflakes in FESEM analysis. The gas-sensing response of Pd (1.12 wt %)-CuO nanoflake-based sensor was measured at 5−100 ppm concentration of different gases, NO 2 , H 2 S, NH 3 , and H 2 , at 125 °C. Gas-sensing tests reveal that the sensitivity of the sensor were 81.7 and 38.9% for 100 and 5 ppm concentrations of NO 2, respectively, which was significantly greater than that of pure CuO. The response and recovery times of the sensor were 72 and 98 s for 100 ppm of NO 2 gas, while they were 90 and 50 s for 5 ppm NO 2 . The calculated limit of detection (LOD) value of the sensor is 0.8235. This appealing LOD is suitable for real-time gas detection. The gas sensor was found to exhibit excellent selectivity toward NO 2 gas and repeatability and stability in humid (80%) conditions. The Pd doping in CuO nanostructures plays a significant role in escalating the sensitivity and selectivity of CuO-based NO 2 gas sensor suitable to work at low operating temperatures.

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“…A recent review nicely summarizes the state of the art in aza-Michael additions of imidazoles. 10 Interestingly it has been stated in that work, that only a few reports on reactions that satisfyingly proceed only in solvent without catalysis are known. The question whether this lack of reactivity is due to the use of unfavorable reaction conditions or the electronic features of azoles remains.…”

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confidence: 99%

Solvent- and catalyst-free aza-Michael addition of imidazoles and related heterocycles

Kodolitsch¹,

Gobec²,

Slugovc³

2020

Preprint

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This work demonstrates the scope and limitations of the aza-Michael addition of imidazoles and related heterocycles with electron deficient olefins under solvent- and catalyst-free conditions. The reaction proceeds at 80°C within hours towards completion as long as the azole derivative is sufficiently soluble in the Michael acceptor, which has been used in small excess. Workup only comprises evaporation of surplus Michael-acceptor and no additional solvents are necessary for purifying the products.<br>

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Aza-Michael Addition of Imidazole Analogues

Cited by 33 publications

References 86 publications

Weak Nucleophiles in the Aza‐Michael Reaction

Weak Nucleophiles in the Aza‐Michael Reaction

Ocimum sanctum Leaf Extract-Assisted Green Synthesis of Pd-Doped CuO Nanoparticles for Highly Sensitive and Selective NO₂ Gas Sensors

Solvent- and catalyst-free aza-Michael addition of imidazoles and related heterocycles

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Aza-Michael Addition of Imidazole Analogues

Cited by 33 publications

References 86 publications

Weak Nucleophiles in the Aza‐Michael Reaction

Weak Nucleophiles in the Aza‐Michael Reaction

Ocimum sanctum Leaf Extract-Assisted Green Synthesis of Pd-Doped CuO Nanoparticles for Highly Sensitive and Selective NO2 Gas Sensors

Solvent- and catalyst-free aza-Michael addition of imidazoles and related heterocycles

Contact Info

Product

Resources

About

Ocimum sanctum Leaf Extract-Assisted Green Synthesis of Pd-Doped CuO Nanoparticles for Highly Sensitive and Selective NO₂ Gas Sensors