Journal of Heterocyclic Chemistry最新文献

A series of dispirooxindole-pyrrolidine/pyrrolizidine derivatives was synthesized in a dioxane-methanol mixture under reflux via a 1,3-dipolar cycloaddition reaction between an azomethine ylide and various 2-heteroarylidene-2,3,4,9-tetrahydrocarbazol-1-ones. The structures of the resulting compounds were confirmed through spectroscopic methods (FT-IR, ¹H-NMR, and ¹³C-NMR) and single-crystal x-ray diffraction analysis. This convergent method demonstrates good generality and functional group tolerance, simplifying both traditional and modern synthetic strategies. The protocol offers advantages such as straightforward workup procedures, higher yields, shorter reaction times, and an environmentally friendly nature. X-ray diffraction analysis also elucidated the stereochemistry and regiochemistry of the spirocyclic adducts.

Graphene oxide (GO) is recognized as the most versatile and multifunctional graphene-based 2D carbonaceous nanomaterial with multifaceted roles in diverse fields. It has been extensively explored in metal-free “carbocatalysis” since 2010. Remarkably, synthesizing medicinally privileged heterocycles using GO as a metal-free and sustainable catalyst has received significant attention in synthetic as well as medicinal chemistry. These GO-catalyzed synthetic approaches are associated with several green chemistry aspects, including multi-component strategies, high atom economy, cost-effectiveness, use of green solvents or solvent-free reaction conditions, energy efficiency, and recyclability of the catalyst. Consequently, these protocols offer sustainable alternatives to conventional metal-catalyzed synthetic approaches for heterocyclic synthesis, reducing waste, costs, energy consumption, and environmental and health impacts. This review provides an in-depth overview of the advancements in the green synthesis of various bioactive N, O, and S-heterocycles using graphene oxide (GO) as a highly efficient, metal-free carbocatalyst over the past decade (2014–2025).

Graphene oxide (GO) is recognized as the most versatile and multifunctional graphene-based 2D carbonaceous nanomaterial with multifaceted roles in diverse fields. It has been extensively explored in metal-free “carbocatalysis” since 2010. Remarkably, synthesizing medicinally privileged heterocycles using GO as a metal-free and sustainable catalyst has received significant attention in synthetic as well as medicinal chemistry. These GO-catalyzed synthetic approaches are associated with several green chemistry aspects, including multi-component strategies, high atom economy, cost-effectiveness, use of green solvents or solvent-free reaction conditions, energy efficiency, and recyclability of the catalyst. Consequently, these protocols offer sustainable alternatives to conventional metal-catalyzed synthetic approaches for heterocyclic synthesis, reducing waste, costs, energy consumption, and environmental and health impacts. This review provides an in-depth overview of the advancements in the green synthesis of various bioactive N, O, and S-heterocycles using graphene oxide (GO) as a highly efficient, metal-free carbocatalyst over the past decade (2014–2025).

Nitro-functionalized pyrazolo[1,5-a]pyrimidines are valuable in materials science and energetics, but traditional methods typically require a mixture of sulfuric and nitric acids. This work presents a mild, iron-complex-mediated strategy for efficient C3-selective nitration of pyrazolo[1,5-a]pyrimidin-7-amines, providing direct access to these important scaffolds. The utility of this versatile method is highlighted by its successful application in late-stage modification, gram-scale synthesis, and further product diversification.

Heterocyclic compounds represent the largest and most diverse group of organic compounds. At present, many heterocyclic compounds have been prepared in increasing numbers due to widespread synthetic research and synthetic utility. Such compounds are useful in medicinal chemistry. Pyrazoline is a heterocycle with a five-membered ring containing two nitrogen atoms, exhibiting significant biological applications. This review highlights recent advances in pyrazoline derivatives synthesis, with particular focus on their biological uses. This study finds a wide variety of pyrazoline derivatives exhibiting promising biological activities, as elaborated in numerous articles. Besides, this review examines the progress achieved in employing pyrazoline derivatives in pharmaceutical and synthetic chemistry from 2020 to 2024.

A triazine-based porous organic polymer as a novel acid catalyst has been prepared for the efficient synthesis of 1,4-dihydropyridine and their derivatives, known as Hantzsch pyridines, under mild reaction conditions. A straightforward one-pot method was adopted for the synthesis of triazine-based porous organic polymer which is anchored by sulfonic acid groups. The presence of multiple sulfonic acid sites in the polymer framework, facilitates the electrophilic activation of the carbonyl groups of both aldehyde and 1,3-dicarbonyl compound, enabling the formation of main intermediates and thereby promoting the efficient formation of 1,4-dihydropyridines. A plausible reaction mechanism for the synthesis of 1,4-DHPs catalyzed by POP CCDABS has also been proposed. This catalyst offers significant advantages, including easy one-step preparation, high product yield, mild reaction conditions, and excellent reusability.

A new series of pyrazoline and pyrazoline–thiazole derivatives conjugated with tetralin ring 5a, b–19 was created starting with the chalcones 3a, b. The new compounds were tested as potential anticancer agents on three human cancer cell lines (HCT-116, HepG-2, and MCF-7) and one human normal cell line (BJ-1). The Compounds 5a, b, 7a, 9a, b, 10, 13a, d, and 16b were identified as strong candidates against the MCF-7 cell line (IC₅₀ = 2.0 ± 0.1–5.6 ± 0.2 μM), where all the compounds exhibited significant activity against the HCT-116 cell line (IC₅₀ = 2.8 ± 0.1–6.5 ± 0.5 μM). Compounds 5b, 9b, and 10 were chosen to study VEGFR-2 inhibitors in comparison with sorafenib (IC₅₀ = 2.9 ± 0.08, 8.6 ± 0.41, 1.1 ± 0.04, and 0.2 ± 0.01 nM, respectively). A molecular docking study was conducted to ascertain the latter compounds' binding interactions with VEGFR-2 kinase.

Herein, we report a reaction condition-dependent metal-free one-pot multicomponent methodology for the efficient synthesis of substituted and fused naphthoquinone derivatives using 2-hydroxy-1,4-naphthoquinone, cinnamaldehyde derivatives, and 2-amino-1,4-naphthoquinone. Refluxing in ethanol with p-TSA (10 mol%) afforded substituted naphthoquinone (4), whereas the reaction in acetic acid under reflux conditions resulted in fused naphthoquinone (5). All of the synthesized compounds were characterized using spectroscopic techniques such as IR, ¹H NMR, ¹³C NMR, and HRMS. This methodology features readily available starting materials, short reaction times, a simple experimental procedure, facile purification, good product yields, and a broad substrate scope.