Lemon juice mediated multicomponent reactions for the synthesis of fused imidazoles

Saha, Argha; Jana, Asim Kumar; Choudhury, Lokman H.

doi:10.1039/c8nj03480j

Cited by 28 publications

(17 citation statements)

References 46 publications

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“…In addition, the catalyst could be reused for at least three runs without loss of catalytic activities. All synthesized compounds (10a-10g) were fully characterized by 1 HNMR and FTIR spectral techniques. We also tested the herbicidal activity of synthesized compounds (10a-10g) against Raphanus sativus L. (Radish) seeds, fungicidal activity against R. solani, A. niger.…”

Section: Discussionmentioning

confidence: 99%

“…The product was dried and recrystallized with ethylacetate to isolate the pure product (10a-10g). Further all the synthesized compounds has been analysed by 1 HNMR and FTIR spectral techniques. The reaction was found to complete within 40 min to give product in quantitative yield (Table 1, Entry 3).…”

Section: Synthesis Of Rice Husk Ashso 3 H (Rhaso H)mentioning

confidence: 99%

“…Lately, one-pot synthesis of potentially bioactive heterocyclic moieties under environmentally friendly conditions has remained one of important topics in organic as well as in medicinal chemistry. Among the multitude of nitrogen-containing heterocycles compounds, imidazole is a key heterocyclic molecule prevalent in many bioactive compounds as well in synthetic drugs (1). A number of methods have been reported for preparation of imidazoles including the condensation reaction of dicarbonyl compounds with substituted aldehydes and ammonium acetate under strong acidic conditions with high temperatures.…”

Section: Introductionmentioning

confidence: 99%

“…All the products (10a-10g) of reactions were isolated in pure form by recrystallized with ethylacetate and no chromatographic techniques were required. All the synthesized compounds (10a-10g) were fully characterized via 1 HNMR and FTIR spectral data and evaluated for in vitro herbicidal activity against Raphanus sativus L. (Radish) seeds. The compounds (10a-10g) were also evaluated for their antifungal activity against Rhizoctonia solani and Aspergillus niger by poisoned food technique method.…”

Section: Introductionmentioning

confidence: 99%

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Solvent-Free Rice Husk Mediated Efficient Approach for Synthesis of Novel Imidazoles and Their <i>In Vitro</i> Bio Evaluation

Sangwan¹,

Singh²,

Gulati

et al. 2021

SSRN Journal

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An e cient and facile route for the synthesis of substituted imidazoles (10a-10g) has been developed by reacting substituted aldehydes (1-7), benzil (8) and ammonium acetate (9) in presence of solid supported acid catalyst viz. Rice Husk Ash.SO 3 H (RHA.SO 3 H) at room temperature. The purity of compounds was con rmed by melting point and thin layer chromatography. After the completion of reaction the crude product was recrystallized with ethylacetate to give pure samples (10a-10g) in good yield. All synthesized compounds (10a-10g) were characterized by 1 HNMR and FTIR spectral techniques. The solid acid catalyst has been characterized by SEM, TEM and X-ray diffraction method. All synthesized compounds were tested in vitro herbicidal activity against Raphanus sativus L. seeds. The compounds (10a-10g) were also screened for their antifungal activity against Rhizoctonia solani and Aspergillus niger by poisoned food technique method. From bio evaluation data, it was found that compounds 10c and 10a were most active against Raphanus sativus L. seeds. Compound 4-(4,5-diphenyl-1H-imidazol-2-yl)phenol (10g) was found most active against R. solani fungus at highest concentration. Compound 2-(4,5-diphenyl-1H-imidazol-2-yl)phenol (10f) has shown maximum percentage inhibition i.e. 71.89 against A. niger at 200 µg/mL concentration.

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Section: Discussionmentioning

confidence: 99%

Section: Synthesis Of Rice Husk Ashso 3 H (Rhaso H)mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Solvent-Free Rice Husk Mediated Efficient Approach for Synthesis of Novel Imidazoles and Their <i>In Vitro</i> Bio Evaluation

Sangwan¹,

Singh²,

Gulati

et al. 2021

SSRN Journal

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“…Synthesis of imidazoles has been reported recently using lemon juice as a catalyst and also using microwave for the multicomponent domino reaction. With our focus on the synthesis of heterocyclic conjugates and the need for developing greener protocols, we decided to investigate the synthesis of benzo[ d ]imidazo[2,1‐ b ]thiazole derivatives by condensation of phenylglyoxal, cyclic enolizable carbonyl compounds, and 2‐aminobenzothiazole under catalyst‐free conditions.…”

Section: Introductionmentioning

confidence: 99%

Catalyst‐free one‐pot regioselective synthesis of benzo[d]imidazo[2,1‐b]thiazoles by heating or grinding

Meena

Saroha

Khurana

et al. 2019

Journal of Heterocyclic Chem

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Eco‐friendly, efficient, and simple one‐pot catalyst‐free new procedures have been reported for the synthesis of benzo[d]imidazo[2,1‐b]thiazoles by condensation of phenylglyoxal, cyclic enolizable carbonyl compounds, and 2‐aminobenzothiazole at 80°C or by grinding the components at room temperature in glycerol. Cyclic enolizable carbonyl compounds employed in the protocol include dimedone, cyclohexa‐1,3‐dione, cyclopenta‐1,3‐dione, 5‐methylcyclohexa‐1,3‐dione, and 4‐hydroxy‐6‐methyl‐2‐pyrone. All the reactions were complete in ~30 min. The structures of all the products were confirmed by spectral data. The structures of compounds IVl and IVe have also been confirmed by X‐ray crystallographic studies. This protocol offers advantages such as short reaction time, easy workup, high yields and an environmentally benign methodology.

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4‐Hydroxycoumarin: A Versatile Substrate for Transition‐metal‐free Multicomponent Synthesis of Bioactive Heterocycles

2021

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One-pot multi-component reactions especially under transition-metal-free catalysis served as an efficient, and environmentally friendly method for the construction of value-added compounds. Their importance in organic synthesis has drastically increased due to their operational simplicity, cost-effectiveness, step-and pot-economic nature. On the other hand, the molecular hybridization concept has recently emerged as a key fascinating area in medicinal and organic chemistry for the design of new drugs. Owing to the widespread occurrence in natural products, and pharmaceutical agents, the incorporation of another heterocycle either as substituents or as a fused material into 4-hydroxycoumarin moiety offers new opportunities for the broad application of the targeted coumarin-heterocycles into many branches of chemistry. Considering the importance of both the topics, here we have reviewed the developments achieved in the synthesis of diverse medicinally privileged oxygen, and nitrogen-containing heterocycles as well as spiro-heterocycles either linked or fused with coumarin moiety by using readily accessible 4-hydroxycoumarin as the starting material via one-pot multi-component reaction under transition-metalfree conditions.[a] B. Borah, K.

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Lemon juice mediated multicomponent reactions for the synthesis of fused imidazoles

Abstract: A green approach for the synthesis of diverse medicinally important tricyclic fused imidazoles has been described using one-pot multicomponent reactions in lemon juice as a biocatalyst as well as the reaction medium.

Cited by 28 publications

References 46 publications

Solvent-Free Rice Husk Mediated Efficient Approach for Synthesis of Novel Imidazoles and Their <i>In Vitro</i> Bio Evaluation

Solvent-Free Rice Husk Mediated Efficient Approach for Synthesis of Novel Imidazoles and Their <i>In Vitro</i> Bio Evaluation

Catalyst‐free one‐pot regioselective synthesis of benzo[d]imidazo[2,1‐b]thiazoles by heating or grinding

4‐Hydroxycoumarin: A Versatile Substrate for Transition‐metal‐free Multicomponent Synthesis of Bioactive Heterocycles

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