One-pot, multicomponent synthesis of symmetrical Hantzsch 1,4-dihydropyridine derivatives using glycerol as clean and green solvent

Sohal, Harvinder Singh; Goyal, Arun; Sharma, Rajeev Kr.; Khare, Rajshree

doi:10.5155/eurjchem.5.1.171-175.943

Cited by 13 publications

(7 citation statements)

References 36 publications

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“…Initially, series 7a – k was synthesized via one-pot Hantzsch condensation of ethyl acetoacetate, ammonium acetate, and various aldehydes, which we have reported earlier. 40 The primary interpretation was done by the comparison of their melting point (MP) and later the spectrum helped in the proper illustration of the synthesized compounds. IR spectra of compound 7a in series 7 exhibits four major absorptions at 3341, 3064, 2982, and 1686 cm –1 corresponding to the N–H, Ar–H, C–H, and C=O groups, respectively.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Initially, series 7a – k was synthesized via one-pot Hantzsch condensation of ethyl acetoacetate, ammonium acetate, and various aldehydes, which we have reported earlier . The primary interpretation was done by the comparison of their melting point (MP) and later the spectrum helped in the proper illustration of the synthesized compounds.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Synthesize Diethyl 2,6-dimethyl-4-phenyl-1,4dihydropyridine-3,5-dicarboxylate (7a−k). Ethyl acetoacetate and benzaldehyde (2:1) were refluxed with the excess of ammonium acetate in the presence of glycerol as an environmentally benign solvent at 90 °C for 1−2 h; 40 the reaction was allowed to cool down before working up in icecold water. The obtained yellow color solid was further recrystallized with ethanol and activated charcoal to obtain opaque white crystalline compound.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

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Highly Efficient Electrocarboxylation Method to Synthesize Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their Antimicrobial Activity

et al. 2022

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1,4-Dihydropyridines (1,4-DHPs) hold a top-notch position in the pharmaceutical world due to a broader spectrum of applications, whereas the carboxylic moiety has been an integral part of the physiological world, effective food preservatives, and antimicrobial agents. Seeking the enormous potential and applications of these two classes, we worked to combine these to synthesize 2,2′-[3,5-bis(ethoxycarbonyl)-4-phenyl-1,4-dihydropyridine-2,6-diyl]diacetic acid the novel dicarboxylic derivatives of 1,4-DHP ( 9a – k ) achieved via the electro-carboxylation of tetrasubstituted-1,4-dihydropyridines ( 8a – k ) derivatives using Mg–Pt electrodes in an undivided cell. The targeted compounds were established by 1 H, 13 C NMR, IR, and ESI-MS. Further, the synthesized compounds show excellent resistance against various microbes and the activity increased 2–3 folds after the introduction of acid groups. Compound 9b (against E. coli , S. aureus , B. subtilis , A. niger , and P. glabrum ), 9d (against E. coli , K. pneumonia , S. aureus , A. janus , and F. oxysporum) , 9f (against E. coli and P. fluorescens ), and 9k (against F. oxysporum and P. glabrum) were found to be highly active at 4 μg/mL with reference to standard amoxicillin and fluconazole. Further, the present synthetic protocol would open new gates for other researchers to develop new molecules by bioisosteres of these substrates.

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Section: Results and Discussionmentioning

confidence: 99%

Section: Results and Discussionmentioning

confidence: 99%

Section: ■ Materials and Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Highly Efficient Electrocarboxylation Method to Synthesize Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their Antimicrobial Activity

et al. 2022

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“…1,4‐Dihyropyridines 9 were prepared by a three‐component reaction of aldehydes 1 , 1,3‐diketone or β ‐diketoester 3 , and ammonium acetate or ammonium carbonate in different media (Methods A‐V, Scheme , Table ) …”

Section: Synthesis Of Six‐membered Heterocyclesmentioning

confidence: 99%

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

Abdella

Abdelmoniem

Abdelhamid

et al. 2020

Journal of Heterocyclic Chem

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Heterocycles represent the largest diversity of organic compounds with signifcant chemical, biomedical, and industrial applications. They exist in numerous natural products, dyes, and as scaffolds in diverse drugs and related pharmaceutically active substances. Substantial attention has been paid to develop various elegant methods to synthesize heterocycles. Among different strategies, Michael and Hantzsch reactions are considered as effective approaches for construction of heterocycles and their corresponding fused derivatives. This review covers this area especially in the last 10 years. The heterocyclic systems reported in this review are classified according to the kind of the heterocyclic systems.

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“…Among the existing methods, till now Hantzsch synthesis is the most common and primitive one. That include multicomponent synthesis by refluxing in solvent like methanol/ethanol, solvent free catalysis approach, microwave assisted, ultrasound assisted, green solvent like glycerol based and many more. However, the above mentioned methods have positives and negatives on one another.…”

Section: Introductionmentioning

confidence: 99%

Effect of Substitutions on 1, 4‐Dihdropyridines to Achieve Potential Anti‐Microbial Drugs: A Review

2019

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1,4‐Dihydropyridines shows good to excellent activity against various microbial strains and their activity can be moulded to the desired extent. Electron withdrawing aromatic groups at position C‐4, esters on C‐3 & C‐5, and small alkyl groups on C‐2 & C‐6 are the best substitutions to achieve potent anti‐microbial drug. Understanding this concept a new age anti‐microbial agents can be synthesized with next level of potency.

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One-pot, multicomponent synthesis of symmetrical Hantzsch 1,4-dihydropyridine derivatives using glycerol as clean and green solvent

Cited by 13 publications

References 36 publications

Highly Efficient Electrocarboxylation Method to Synthesize Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their Antimicrobial Activity

Highly Efficient Electrocarboxylation Method to Synthesize Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their Antimicrobial Activity

Synthesis of heterocyclic compounds via Michael and Hantzsch reactions

Effect of Substitutions on 1, 4‐Dihdropyridines to Achieve Potential Anti‐Microbial Drugs: A Review

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