The Spotlight Review on Ionic Liquids Catalyzed Synthesis of Aza- and Oxa-Heterocycles Reported in 2021

Means of eliminating water pollutants or transforming them into less hazardous compounds by green catalysis are desired. The current work was developed with the goal of discovering supports suited for laccase (Lc) immobilization. The effect of the chitosan (CS) molecular weight (Mw) or the polyacrylic acid (PAA) addition was evaluated in microsphere formulation and enzyme immobilization by ESEM, rheology, operational stability, and kinetics. As a practical application, the synthesized products were tested in the methyl red (MR) decomposition and the product identification was performed by high-resolution mass spectrometry. Depending on the required properties, the laccase activity profile (pH, temperature, storage, and Michaelis–Menten parameters) and rheological strength can be modulated by varying the molecular mass of CS or by adding PAA in the support formulation. The immobilized products having the best features regarding MR degradation and recycling abilities were the medium Mw CS microspheres and the system with low Mw CS complexed by PAA, respectively. The degradation mechanism of the dye was proposed accordingly with the identified products by mass spectroscopy. The findings emphasize the potential of the proposed immobilization products to be exploited as viable biocatalysts for dye-contaminated water.

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The Immobilization of Laccase on Mixed Polymeric Microspheres for Methyl Red Decomposition

A bimetallic synthesis of 2-arylindoles from alcohols and anilines is described. The dehydrogenation or oxidation of a secondary alcohol were performed by Ni- and Mn-catalyzed reactions, respectively. The formed ketone was converted into an imine intermediate that was later cyclized to the corresponding 2-arylindole by a Pd-catalyzed oxidative cyclization. A set of 2-arylindoles was prepared, without isolation of the intermediates generated. The compatibility of the catalysts was investigated, and the optimized protocol opens room for the integration of Earth abundant metals and palladium complexes to improve the sustainability of the synthesis of N-heterocycles.

Bimetallic Catalyzed Synthesis of 2-Arylindoles

Indazoles are a very important group of nitrogen-containing heterocycles with a wide range of biological and medicinal applications. These properties make them highly attractive for drug development, particularly when combined with sulfonamides to enhance their medicinal potential. In this work, we synthesized an indazole-based sulfonamide, namely the 1-((2-chloro-5-methoxyphenyl)sulfonyl)-5-nitro-1H-indazole (3). The reduction of the nitro group of 5-nitroindazole (1) to its corresponding amine was also performed to yield compound (4). Both compounds’ structures were elucidated using various spectroscopic techniques such as 1H NMR, 13C NMR, infrared (IR), and high-resolution mass spectrometry (HRMS). Our molecular docking studies suggest that compounds (3) and (4) have a strong affinity for MAPK1, indicating their potential as cancer treatments. 

Synthesis and Characterization of Novel Indazole–Sulfonamide Compounds with Potential MAPK1 Inhibitory Activity for Cancer Treatment

An efficient nickel‐catalyzed sequential one‐pot strategy for the synthesis of coumarin‐appended quinolines and bis‐quinolines has been developed under mild reaction conditions in moderate to good yields (up to 84%) via dehydrogenative Friedlander annulation followed by C(sp3)‐H functionalization. The utilization of cheap and readily available starting materials, environmentally friendly solvents, and simple operating procedures are the attractive attributes of this method. Additionally, the photophysical properties of the synthesized derivatives were explored utilizing UV‐vis absorption and fluorescence emission studies. Furthermore, the large‐scale synthesis and the synthetic utility of the derivatives highlight the potential applicability of this strategy in synthetic organic chemistry. Moreover, A plausible reaction mechanism is supported by the control experiments and reaction monitoring by 1H NMR analysis. 

Nickel‐Catalyzed Sequential Synthesis of Alkylated Quinolines and Their Photophysical Studies

N-heterocycles, both saturated and unsaturated, are ubiquitous biologically active molecules that are extremely appealing scaffolds in drug discovery programs. Although classical synthetic methods have been developed to access many relevant N-heterocyclic scaffolds, representing well-established and reliable routes, some do not meet the needs of sustainability. In this context, several advances have been made towards the sustainable synthesis of N-heterocycles. This review focuses on the most recent examples from the last five years of catalytic synthesis of several heterocyclic compounds of medicinal relevance. Thus, the synthesis of isoindoloquinazolines, quinazolines and azaindoles, among others, are covered. The synthetic methods selected include the use of homogeneous and heterogeneous catalysts and the use of alternative and sustainable methods such as, for example, metal-catalyzed acceptorless coupling and one-pot reactions. The green aspects of the individual synthetic approaches are highlighted, and the scope of each methodology is described.

Advances in Green Catalysis for the Synthesis of Medicinally Relevant N-Heterocycles

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Advances in Green Catalysis for the Synthesis of Medicinally Relevant N-Heterocycles