One pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride using sodium sulphate (anhyd) and sodium bicarbonate in dry media under microwave irradiation

Singh, Sharwan K Dewan. Ravinder; Kumar, Anil

doi:10.3998/ark.5550190.0007.204

Cited by 6 publications

(2 citation statements)

References 9 publications

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“…Oximes are employed as intermediates in the preparation of caprolactam, which is a precursor of nylon 6 [ 6 ]. The transformations to nitriles [ 7 ], nitro products [ 8 , 9 ], nitrones [ 10 ], amines [ 11 ], and aza heterocycles [ 12 ] are some of the synthetic uses of oximes. It has been reported that oximes are also useful reagents for selective activation [ 13 ] and widely employed as intermediates for the synthesis of amides by Beckmann rearrangement [ 14 , 15 ], fungicides, and herbicides [ 16 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, DFT, and Anticancer Activity of Some Imine-Type Compounds via Routine Schiff Base Reaction: An Example of Unexpected Cyclization to Oxazine Derivative

et al. 2023

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The synthesis, characterization, and anticancer properties of three imine-type compounds 1–3 and an unexpected oxazine derivative 4 are presented. The reaction of p-dimethylaminobenzaldehyde or m-nitrobenzaldehyde with hydroxylamine hydrochloride afforded the corresponding oximes 1–2 in good yields. Additionally, the treatment of benzil with 4-aminoantipyrine or o-aminophenol was investigated. Routinely, the Schiff base (4E)-4-(2-oxo-1,2-diphenylethylideneamino)-1,2-dihydro-1,5-dimethyl-2-phenylpyrazol-3-one 3 was obtained in the case of 4-aminoantipyrine. Unexpectedly, the reaction of benzil with o-aminophenol proceeded with cyclization to produce the 2,3-diphenyl-2H-benzo[b][1,4]oxazin-2-ol 4. The structures of compounds 3 and 4 were unambiguously determined by single crystal X-ray diffraction. Hirshfeld analysis of molecular packing revealed the importance of the O…H (11.1%), N…H (3.4%), C…H (29.4%), and C…C (1.6) interactions in the crystal stability of 3. In the case of 4, the O…H (8.8%), N…H (5.7%), and C…H (30.3%) interactions are the most important. DFT calculations predicted that both compounds have a polar nature, and 3 (3.4489 Debye) has higher polarity than 4 (2.1554 Debye). Different reactivity descriptors were calculated for both systems based on the HOMO and LUMO energies. The NMR chemical shifts were calculated and were found well correlated with the experimental data. HepG2 growth was suppressed by the four compounds more than MCF-7. The IC50 values of 1 against HepG2 and MCF-7 cell lines were the lowest, and it is considered the most promising candidate as an anticancer agent.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Crystal Structure, DFT, and Anticancer Activity of Some Imine-Type Compounds via Routine Schiff Base Reaction: An Example of Unexpected Cyclization to Oxazine Derivative

et al. 2023

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“…Te reaction mixture was extracted with CH 2 Cl 2 , and the extracts were dried over Na 2 SO 4 anhydrous. Te product was isolated and characterized by comparing its spectroscopic data with an authentic sample where appropriate[35] as follows: CDCl 3 ) δ: 7.23 (2H, d, J � 7.4 Hz, H-Ar), 7.47 (2H, d, J � 7.4 Hz, H-Ar). IR (KBr, ] max , cm −1 ): 3055, 2224 cm −1 [35].…”

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confidence: 99%

Unlocking the Potential of NiSO4·6H2O/NaOCl/NaOH Catalytic System: Insights into Nickel Peroxide as an Intermediate for Benzonitrile Synthesis in Water

Shoair,

Almalki,

Shanab

et al. 2023

Journal of Nanotechnology

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Nickel peroxide nanoparticles (NPNPs) were prepared and characterized using various techniques including transmission electron microscope (TEM), scan electron microscope (SEM), energy dispersive spectrometer (EDS), X-ray diffraction (XRD), and FTIR spectra. The aqueous basic catalytic system NiSO4·6H2O/NaOCl/NaOH (pH = 14) was investigated for the catalytic dehydrogenation of benzylamine and parasubstituents to their corresponding nitriles at room temperature. The obtained results confirmed the formation of NiO2 nanocrystalline particles with a size of 20 nm. Benzylamine with electron-donating groups showed higher yields of nitriles compared to electron-withdrawing groups. The mechanism involved in the in situ generated NiO2 nanoparticles dehydrogenating benzylamine to benzonitrile, with the produced NiO converting back to NiO2 nanoparticles through the excess of NaOCl.

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Computational Investigation of Substituent Effects on the Formation and Intramolecular Cyclization of 2′-Arylbenzaldehyde and 2′-Arylacetophenone Oxime Ether Radical Cations

et al. 2019

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This work describes our computational study of substituent effects on the formation and cyclization of 2′-arylbenzaldehyde and 2′-arylacetophenone oxime ether radical cations. Recent experimental work by de Lijser and co-workers has demonstrated that these reactive intermediates, which are generated through photoinduced electron transfer (PET) with a photosensitizer, undergo intramolecular cyclization to yield substituted phenanthridines. The experimental study further showed correlations between the yield of cyclized products and the Hammett σ Para + parameter of the substituent on the aryl group, with both strongly electronwithdrawing and electron-donating substituents shown to significantly reduce the product yield. By analyzing the ΔG PET associated with radical cation formation as well as the thermodynamics and kinetics of radical cation cyclization, we provide an explanation for these observations. We then computationally extend this mechanistic analysis to 2′-arylbenzaldehyde oxime ethers with substituents also present on the central benzene ring and show that such substituents generally have a larger impact on the PET-induced cyclization than those on the aryl group. Overall, this work extends our understanding of the overall scope of this photooxidative route toward substituted phenanthridines as well as makes clear predictions as to how the formation of oxime ether radical cations can be tuned by substituents.

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One pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride using sodium sulphate (anhyd) and sodium bicarbonate in dry media under microwave irradiation

Abstract: A rapid and facile one pot synthesis of nitriles has been carried out in high yields from the corresponding aldehydes and hydroxylamine hydrochloride in the presence of environmentally benign sodium sulphate (anhyd) and sodium bicarbonate catalysts in dry media under microwave irradiation.

Cited by 6 publications

References 9 publications

Synthesis, Crystal Structure, DFT, and Anticancer Activity of Some Imine-Type Compounds via Routine Schiff Base Reaction: An Example of Unexpected Cyclization to Oxazine Derivative

Synthesis, Crystal Structure, DFT, and Anticancer Activity of Some Imine-Type Compounds via Routine Schiff Base Reaction: An Example of Unexpected Cyclization to Oxazine Derivative

Unlocking the Potential of NiSO4·6H2O/NaOCl/NaOH Catalytic System: Insights into Nickel Peroxide as an Intermediate for Benzonitrile Synthesis in Water

Computational Investigation of Substituent Effects on the Formation and Intramolecular Cyclization of 2′-Arylbenzaldehyde and 2′-Arylacetophenone Oxime Ether Radical Cations

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