A Simple, Efficient Green Protocol for the Synthesis of β‐Enaminone and Enamino Ester Derivatives by Using Onion Extract as Green Catalyst

Prabakaran, Kaliyan; Sivakumar, Muthusamy; Seenivasaperumal, M.

doi:10.1002/slct.201601515

Cited by 13 publications

(5 citation statements)

References 44 publications

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“…2 in the presence of water extract of onion (3 mL) at 90°C for 12 hours in DMF (5 mL) gave the mixture of 2‐substituted 3 benzimidazoles (67%) and 1,2‐disubstituted (28%) 4 benzimidazoles (Table 1, entry 1). The method of preparation of required water extract of onion reported earlier from our research group 45 . Primarily, efforts were undertaken towards chemoselective synthesis of 2‐substituted benzimidazole derivatives 3 (Scheme 1; method A).…”

Section: Resultsmentioning

confidence: 99%

“…In continuation of our previous work for the development of green synthetic procedure [45][46][47] using water extract of onion as catalyst, we are very much interested to develop the cost reductive, chemoselective synthesis of 2-substituted benzimidazole derivatives 3 and 1,2-disubstituted benzimidazole derivatives 4, we have examined the reaction of ophenylenediamine (1 equiv.) 1 with aldehyde (2 equiv.)…”

Section: Resultsmentioning

confidence: 99%

“…The method of preparation of required water extract of onion reported earlier from our research group. 45 Primarily, efforts were undertaken towards chemoselective synthesis of 2-substituted benzimidazole derivatives 3 (Scheme 1; method A). Accordingly, to achieve the target we have play around three parameters such as equivalent of the substrates, polarity of the solvent, and loading of the catalyst.…”

Section: Resultsmentioning

confidence: 99%

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Water extract of onion catalyst: An economical green route for the synthesis of 2‐substituted and 1,2‐disubstituted benzimidazole derivatives with high selectivity

Prabakaran

Selvaraj

Seenivasaperumal

2020

Journal of Heterocyclic Chem

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An efficient, environmental friendly and substrate controlled method of synthesis of 2‐substituted benzimidazole derivatives 3 and 1,2‐disubstituted benzimidazole derivatives 4 with high selectivity has been achieved from the reaction of o‐phenylenediamine 1 and aldehydes 2 in the presence of water extract of onion and selecting suitable reaction medium. This method is widely applicable for variety of aldehydes such as aromatic/aliphatic/heterocyclic aldehydes and 1,2‐diamines to afford 2‐substituted benzimidazole derivatives 3 and 1,2‐disubstituted benzimidazole derivatives 4 in good to excellent yields (up to 96%). The developed method of water extract of onion catalysis produced 2‐substituted benzimidazoles 3 from aromatic aldehydes having electron‐withdrawing groups, whereas aromatic aldehydes bearing electron donating groups selectively furnished 1,2‐disubstituted benzimidazole 4 derivatives. The process described here has several advantages of cheap, low energy consumption, commercially available starting materials, operational simplicity and nontoxic catalyst. The use of water extract of onion makes this present methodology green and giving a useful contribution to the existing methods available for the preparation of benzimidazole derivatives. In addition, Hammett correlation of substituent constant (σ) vs percentage (%) yield has been established.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Water extract of onion catalyst: An economical green route for the synthesis of 2‐substituted and 1,2‐disubstituted benzimidazole derivatives with high selectivity

Prabakaran

Selvaraj

Seenivasaperumal

2020

Journal of Heterocyclic Chem

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“…All chemical reagents were purchased from commercial sources and used as received unless otherwise indicated. Known compounds 1a – c , 1d , 1e , and 1h , 1j , 1k , 1o , 1r , and 1z3 , 1l and 1m , 1w , 1x , and 1z5 , 3s and 3t , 5a , and 5b were prepared as reported. Compound 7b is known, and its spectroscopic feature is in good agreement with that reported in the literature.…”

Section: Methodsmentioning

confidence: 99%

Amide Bond Formation Assisted by Vicinal Alkylthio Migration in Enaminones: Metal- and CO-Free Synthesis of α,β-Unsaturated Amides

Liu

Huang

et al. 2018

J. Org. Chem.

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Amide bond formation is one of the most important transformations in organic synthesis, drug development, and materials science. Efficient construction of amides has been among the most challenging tasks for organic chemists. Herein, we report a concise methodology for amide bond (-CONH-) formation assisted by vicinal group migration in alkylthio-functionalized enaminones (α-oxo ketene N, S-acetals) under mild conditions. Simple treatment of such enaminones with PhI(OAc) at ambient temperature in air afforded diverse multiply functionalized α,β-unsaturated amides including β-cyclopropylated acrylamides, in which a wide array of functional groups such as aryl, (hetero)aryl, alkenyl, and alkyl can be conveniently introduced to a ketene moiety. The reaction mechanism was investigated by exploring the origins of the amide oxygen and carbon atoms as well as isolation and structural characterization of the reaction intermediates. The amide bond formation reactions could also be efficiently performed under solventless mechanical milling conditions.

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“…The carbonyl group conjugated to the enamine moiety provides sufficient stability for this system to be easily prepared, isolated and stored at room temperature under atmospheric conditions [1] ,therefore, They have also been made use of as starting materials for the synthesis of anti-inflammatory, antibacterial, anticonvulsant and antitumor agents [2] , as well as in the production of naturally occurring alkaloids. The significant advantages of enaminone derivatives are their stability under simulated physiological pH conditions and low level of toxicity [3] . The conjugated system of βenaminone function is regarded as a functional group in the drug industry.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Biological Activity of Mixed ligand Complexes from 8-Hydroxyquinoline and new Ligand for β-Enaminone

Abdulsalam¹,

Numan²

2022

PJMHS

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The synthesized ligand [4-chloro-5-(N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)sulfamoyl)-2-((furan-2-ylmethyl)amino)benzoic acid] (H2L1) was identified utilizing Fourier transform infrared spectroscopy (FT-IR), 1 H, 13 C – NMR, (C.H.N), Mass spectra, UV-Vis methods based on spectroscopy. To detect mixed ligand complexes, analytical and spectroscopic approaches such as micro-analysis, conductance, UV-Visible, magnetic susceptibility, and FT-IR spectra were utilized. Its mixed ligand complexes [M(L1)(Q)Cl2] [ where M= Co(II), Ni(II), and Cd(II)] and complexes [Pd(L1)(Q)] and [Pt(L1)(Q)Cl2]; [H2L1] =β-enaminone ligand =L1 and Q= 8-Hydroxyquinoline = L2]. The results showed that the complexes were synthesised utilizing the molar ratio M: L1:L2 (1 :1 :1). The formation of six-coordinate octahedral geometry was proposed for metal complexes Co (II), Ni (II), Cd (II), and Pt (IIII), while the Pd (II) complex was square planar. By using the agar well diffusion method, the ligands and complexes were evaluated for antibacterial activity against Staphylococcus aureus, Escherichia coli. The studies demonstrate that the ligand and its complexes have variable activity against the bacterial types, Some of the complexes had an effect on bacteria, while others had less inhibitory action than the ligand. Also, the produced ligand and its metal complexes have been tested for fungi (Candida albicans );the complexes exhibited suppressing activity against fungi compared to the ligand prepared from them. Keywords: β-enaminones, 5,5-dimethylcyclohexane-1,3-dione , Furosemide, Mixed-ligand complexes, 8-Hydroxyquinoline.

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A Simple, Efficient Green Protocol for the Synthesis of β‐Enaminone and Enamino Ester Derivatives by Using Onion Extract as Green Catalyst

Cited by 13 publications

References 44 publications

Water extract of onion catalyst: An economical green route for the synthesis of 2‐substituted and 1,2‐disubstituted benzimidazole derivatives with high selectivity

Water extract of onion catalyst: An economical green route for the synthesis of 2‐substituted and 1,2‐disubstituted benzimidazole derivatives with high selectivity

Amide Bond Formation Assisted by Vicinal Alkylthio Migration in Enaminones: Metal- and CO-Free Synthesis of α,β-Unsaturated Amides

Synthesis, Characterization, and Biological Activity of Mixed ligand Complexes from 8-Hydroxyquinoline and new Ligand for β-Enaminone

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