A catalytic and green method for one-pot synthesis of new Hantzsch 1,4-dihydropyridines

Jassem, Ahmed Majeed; Almashal, Faeza Abdul Kareem; Mohammed, Mohammed Qasim; Jabir, Hadi Abdal Samad

doi:10.1007/s42452-020-2165-x

Cited by 13 publications

(6 citation statements)

References 37 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…During the last few decades, ionic liquids as green catalysts were used for different reactions, including Hantzsch reaction. For example, betainium-based ionic liquids were used for the one-pot production of acridinediones through Hantzsch reactions under mild conditions [27], β-cyclodextrin/imidazolium based dicationic ionic liquid in the one-pot, three-component Hantzsch reaction [28], 3-methyl-1-sulfonic acid imidazolium chloride as an acidic ionic liquid in four-component Hantzsch reaction leading to a simple synthetic procedure, short reaction times, less pollution and high yields of the products [29]. Bromination of 2,6-methyl groups of the 3,5-bis(dodecyloxycarbonyl)-2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine (5) was performed with NBS according to the previously described procedure [26].…”

Section: Discussionmentioning

confidence: 99%

Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide

Ruciņš

Pajuste

Plotniece

et al. 2021

Molbank

View full text Add to dashboard Cite

In the present work, construction of double-charged cationic amphiphilic 1,1′-{[3,5-bis(dodecyl¬oxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) dibromide (7) was performed in four steps. Dodecyl 3-oxobutanoate (1) was condensed with thiophene-3-carbaldehyde (2) which was necessary for Hantzsch cyclisation dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3). Two-component Hantzsch type cyclisation of dodecyl (E/Z)-3-aminobut-2-enoate (4) and dodecyl (E/Z)-3-oxo-2-(thiophen-3-ylmethylene)butanoate (3) gave 3,5-bis(dodecyloxycarbonyl)-2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine (5). Bromination of compound 5 followed by nucleophilic substitution of bromine with pyridine gave the desired cationic amphiphilic 1,4-dihydropyridine 7. The obtained target compound 7 and new intermediates 3, 5 and 6 were fully characterised by IR, UV, 1H NMR, 13C NMR, HRMS or microanalysis. Characterisation of nanoparticles formed by the cationic 1,4-dihydropyridine 7 in an aqueous solution was performed by DLS measurements.

show abstract

Section: Discussionmentioning

confidence: 99%

Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide

Ruciņš

Pajuste

Plotniece

et al. 2021

Molbank

View full text Add to dashboard Cite

show abstract

“…Ionic liquid [(Msim)Cl] was prepared, referring to the procedure in the reference [13] . In a round‐bottomed flask (250 mL), 1‐methylimidazole (1.65 g, 20 mmol) was dissolved in dry CH 2 Cl 2 (100 mL).…”

Section: Methodsmentioning

confidence: 99%

“…Among Brønsted ILs, 3‐methyl‐1‐sulfonic acid imidazolium chloride [(Msim)Cl] used in many acid‐catalyzed processes has aroused good attention because it combines the benefits of mineral and solid acids [12] . [(Msim)Cl] is increasingly used in many multicomponent reactions, such as the Hantzsch reaction [13] . Therefore, intense efforts are directed toward the discovery or development of environmentally benign ILs in multicomponent reactions.…”

Section: Introductionmentioning

confidence: 99%

Sonochemical‐Promoted Multicomponent Synthesis of a New Amidoalkyl Naphthol Derivative Catalyzed by [(Msim)Cl] Ionic Liquid and Assessment of Its Nonlinear Optical Properties

Muala Dhumad,

Hassan,

Jassem

et al. 2024

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

The sonochemical‐assisted multicomponent reaction catalyzed by ionic liquid, solvent‐free synthesis, improving chemical structure, computational calculations, and nonlinear optical properties (NLO) assessment of a new amidoalkyl naphthol derivative 4, that is, [N‐((2‐hydroxynaphthalen‐1‐yl)(4‐nitrophenyl)methyl)‐2‐phenylhydrazinecarbothioamide (C24H20N4O3S), are introduced. The corrected structure of the synthesized derivative 4 is confirmed by different spectroscopic techniques viz., (1H and 13C) NMR, Infrared radiation (IR), Mass spectra, and UV‐vis. spectra. To obtain geometrical structure and confirm the experimental findings, DFT‐assisted B3LYP/6‐31G* method is used. The NLO properties of the synthesized derivative are studied using two visible laser beams where its nonlinear refraction index (NLRI) at 473 nm cw laser beam is obtained using diffraction patterns (DPs) and the Z‐scan techniques. As high as 5.312×10−11 m2/W of NLRI is obtained. The all‐optical switching (AOS) which is usually carried out utilizing two laser beams, the controlling and controlled, is generalized by the use of three laser beams, controlling, 473 nm beam and two controlled 532 nm and 635 nm beams.

show abstract

“…With the aid of 10 mol% of 3‐methyl‐1‐sulphonic acid imidazolium chloride ([Msim]Cl) as the catalytic system, the desired 1,4‐dihydropyridine products 44 were obtained in 80–93 % yields (Scheme 19). [40] The notable advantages of the protocol include mild process, simple workup procedure, green solvent system, good yield of the products, etc. However, the narrow substrate scopes point toward the limitations of the current strategy otherwise ground‐breaking developments.…”

Section: Synthesis Of 14‐dihydropyridines Via One‐pot Reactions Under...mentioning

confidence: 99%

Recent Advances and Prospects in the Transition‐Metal‐Free Synthesis of 1,4‐Dihydropyridines

et al. 2022

View full text Add to dashboard Cite

The synthesis of novel nitrogen‐containing heterocycles as a result of their frequent existence in natural products, commercially available drugs, and optoelectronic materials is extremely demanding but challenging due to the involvement of toxic solvents, and sometimes transition‐metal catalyst(s) which are often associated with environmental safety concerns. 1,4‐dihydropyridine (1,4‐DHP), of synthetic and natural origin, are among one of the privileged classes of nitrogen‐containing heterocycles, representing a broad spectrum of pharmaceutical properties, and has received considerable interest in medicinal and synthetic organic chemistry. Recognizing the prominent significance of this structural motif, substantial efforts have been paid not only for their expedient synthesis but also for the discovery of novel complex molecules by using them as key active building blocks. However, developing elegant synthetic processes provides effortless access to 1,4‐dihydropyridines by exploring environmentally friendly conditions with the primary goal of lowering the expenditure of the overall process is extremely demanding but challenging. In this mini‐review article, we have demonstrated a clear presentation of the recent transition‐metal‐free catalyzed synthesis of 1,4‐dihydropyridines of potential therapeutic interests and covered the literature from 2015 to date.

show abstract

A catalytic and green method for one-pot synthesis of new Hantzsch 1,4-dihydropyridines

Cited by 13 publications

References 37 publications

Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide

Synthesis and Characterisation of 1,1′-{[3,5-Bis(dodecyloxy-carbonyl)-4-(thiophen-3-yl)-1,4-dihydropyridine-2,6-diyl]bis-(methylene)}bis(pyridin-1-ium) Dibromide

Sonochemical‐Promoted Multicomponent Synthesis of a New Amidoalkyl Naphthol Derivative Catalyzed by [(Msim)Cl] Ionic Liquid and Assessment of Its Nonlinear Optical Properties

Recent Advances and Prospects in the Transition‐Metal‐Free Synthesis of 1,4‐Dihydropyridines

Contact Info

Product

Resources

About