The diisopropyl ethyl ammonium acetate (DIPEAc)-promoted
Biginelli
protocol has been developed for the first time by a successive one-pot
three-component reaction of aldehydes, ethylcyanoacetate/ethyl acetoacetate,
and thiourea/urea to afford pharmacologically promising 1,2,3,4-tetrahydropyrimidines
in high yields at room temperature. The key benefits of the present
scheme are the capability to allow a variability of functional groups,
short reaction times, easy workup, high yields, recyclability of the
catalyst, and solvent-free conditions, thus providing economic and
environmental advantages. In addition, a series of 4-oxo-6-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles
analogues were synthesized and selected for their in vitro antifungal
and antibacterial activities.
An
economic, sustainable, and straightforward environmentally friendly
synthesis of highly diversified polyfunctional dihydrothiophenes is
successfully achieved via diisopropyl ethyl ammonium acetate as a
room-temperature ionic liquid. Multicomponent synthesis contains domino
processes; the benefit of this present protocol is highlighted by
its readily available starting materials, superior functional group
tolerance, purity of synthesized compounds was checked by high-performance
liquid chromatography results in up to 99.7% purity for the synthesized
compounds, reaction mass efficiency, effective mass yield, and excellent
atom economy. In addition, a series of 2-(N-carbamoyl
acetamide)-substituted 2,3-dihydrothiophene analogs were synthesized,
and selected samples were chosen for testing their in vitro antibacterial
and antifungal activities. Furthermore, a molecular docking study
against sterol 14α-demethylase could provide valuable insight
into the mechanism of antifungal action providing an opportunity for
structure-based lead optimization.
An eco-friendly multicomponent synthesis of substituted imidazole derivatives catalyzed by β-cyclodextrin (β-CD) was scrutinized for the first time via a onepot three-compound reaction of aldehyde, isatin, and ammonium acetate in H 2 O-EtOH at 80°C. β-CD is a supramolecule, highly efficient, biodegradable, and recyclable catalyst used to produce high yields of desired 1, 8dihydroimidazo[2,3-b]indoles. The developed protocol contains number of advantages like nontoxic, inexpensive catalyst; green reaction condition; easily available starting material; shorter reaction time; and good yields.
An operationally simple, one-pot multicomponent reaction has been developed for the assembly of pyrido [2,3-d]pyrimidine and pyrazolo [3,4b]pyridine derivatives (4a−4am) in excellent yields (92−94%) with high purity. The reactions were easy to perform simply by mixing of electron-rich amino heterocycles (including aminouracils and aminopyrazoles), aldehyde, and acyl acetonitrile in the presence of [Et 3 NH][HSO 4 ] under solvent-free conditions. The remarkable feature of the present approach is that the ionic liquid possesses dual solvent-catalytic engineering capability. Results of this study revealed that 1 mmol of the ionic liquid catalyst under solvent-free conditions at 60 °C is the best reaction parameter for the construction of fused pyridine and pyrimidine derivatives in excellent yields. The present methodology showed good results under gram-scale conditions, thereby indicating its applicability in industrial as well as academic settings in the near future.
The synthesis of a combinatorial library of heterocycle-fused pyridine derivatives has been achieved successfully via a one-pot four-component reaction of aromatic/aliphatic aldehyde, malononitrile, thiazolidine-2,4-dione and ammonium acetate in the presence of piperidinium acetate as the catalyst. It involved the Knoevenagel condensation of the aldehyde and malononitrile to produce arylidene malononitrile as an intermediate, which was further intramolecular cyclization through Michael type addition ketone to the electrophilic double bond of the arylidene to produce fused pyridines in high yields. Environmental friendliness, low cost, Operational simplicity, extensive reusability and applicability, and easy recovery of the catalyst using simple evaporation are the critical features of this methodology. Also, a series of pyridine based dihydrothiazolo[4,5-b] pyridine-6-carbonitrile analogs were synthesized and selected for their in vitro antifungal and antibacterial activities.
The synthesis of a new series 1-(3-methoxy-4-((1-phenyl-1H-1,2,3-triazole-4-yl)methoxy) phenyl)ethanone via click chemistry approach utilizing azide-alkyne cycloaddition reactions is reported in this study. The structures of all newly synthesized compounds were analyzed by IR, NMR, and Mass spectral techniques. All the newly synthesized compounds were subjected to cytotoxicity assay against a panel of three human cancer cell lines (HepG2, A549, and MCF-7) using 3-(4,5-dimethylthiazole-2-yl)-2,5-diphenyltetrazolium bromide (MTT), to check in vitro anticancer activity. Compound 5 b was found to be the most potent anticancer agents with IC 50 value 3.42 μM, 1.26 μM, and 5.96 μM against HepG2, A549, and MCF-7 respectively. Among the tested compounds, 5 a and 5 q have shown notable anticancer activity as compared to the reference drug, Adriamycin [a] A
In this study, we report the use of a 1,8‐diazabicyclo [5.4.0]‐undec‐7‐en‐8‐ium imidazolate ionic liquid as a catalyst as well as a green solvent for the expeditious multicomponent transformation of tetra‐ and trisubstituted imidazole scaffolds via four‐ and pseudo‐four‐component reactions with short reaction time, excellent yield, and purity of products. The ionic liquid is cheap, biodegradable, and can be recovered and reused for more than five consecutive cycles. The advantage of this protocol for gram‐scale synthesis adds to its practical applicability. Selected synthesized tetra‐ and trisubstituted imidazole scaffolds were screened for their in vitro antiproliferative properties against the human cancer cell lines EC‐109, MCF‐7, HGC‐27, and PC‐3. Compounds 4m, 5e, and 5v showed potent cytotoxic activity against the human breast cancer cell line PC‐3, MCF‐7, and HGC‐27, respectively.
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