Nitrogen-containing Compounds Research Articles

Protein quality, nutrition and health

Dietary proteins are energy macronutrients providing nitrogen, amino acids (AA), and energy. AAs are the main nitrogen-containing compounds in the body and are the precursors for the synthesis of body proteins and of several other AA-derived molecules. Among the 20 AAs included in protein sequence, 9 are classified as “nutritionally essential” or “indispensable” AA (IAA) because they cannot be synthesized in the body and must be provided by the diet. IAAs are limiting components for protein synthesis. An adequate intake of protein is required to support growth, maintenance, body functions, health and survival. Official definition of protein requirement is based on nitrogen balance. Protein quality is related to the capacity of protein to provide an adequate quantity of nitrogen and of each of the 9 IAAs for the different physiological situations in humans. Protein source is considered high quality for humans when the protein is readily digested, simultaneously providing an adequate quantity of nitrogen and of each of the 9 IAAs to maintain an adequate metabolic AA pool. The most accurate assessment of protein quality of foods for humans is through metabolic studies that measure nitrogen balance. The protein quality score is the ratio of the content of each IAA in the food and in a reference profile. This score corresponds to the calculated composition of a protein which, when meeting protein requirements, simultaneously meets the requirements of each of the 9 IAAs. AA scores as predictors of protein quality must be adjusted for protein and AA availability.

Ru and Ruδ+ synergistic catalysis efficiently promotes 2,2,6,6-Tetramethyl-4-Piperidone hydrogenation for 2,2,6,6-Tetramethyl-4-Piperidinol preparation

The catalytic hydrogenation of nitrogen-containing heterocyclic compounds is a crucial process; however, nitrogen removal severely restricts product selectivity. Consequently, this study utilized a simple heat treatment method to synthesize ruthenium (Ru)-based catalysts supported on N-doped activated carbon for application in the selective catalytic hydrogenation of 2,2,6,6-Tetramethyl-4-piperidone (TAA). The results show that the selectivity of 2,2,6,6-Tetramethyl-4-piperidinol (TMP) is as high as 99.87 % under the premise of almost complete TAA reaction. The catalyst was characterized using N2-physisorption-desorption, XRD, TEM, Raman, XPS, ICP-OES, and H2-TPR techniques. N-doped activated carbon introduced numerous defect sites to the catalyst, improved the surface wettability of the activated carbon support, provided abundant active metal anchoring sites, which results in highly uniform dispersion of Ru nanoparticles (NPs) on the carrier surface, forms relatively smaller nanoparticles, and enhances the catalyst's activity. Additionally, a strong interaction exists between the active metal Ru and N-doped activated carbon support. Thus, the transfer of free electrons from Ru to N species was facilitated, and the relative content of Ruδ+ in the catalyst was increased, and the synergistic effect between Ru and Ruδ+ contributes to improving the catalyst's performance. This work holds significant potential for controlling the selectivity of nitrogen-containing heterocyclic compounds in the catalytic hydrogenation process.

Research progress on the toxicity of Asari Radix et Rhizoma

Asari Radix et Rhizoma (ARR), also known as Xixin, has been broadly used as a traditional herbal medicine in East Asia and is an important component of classic prescriptions, including mahuang fuzi xixin decoction. It was initially classified as a “top grade” herb in ancient Chinese Pharmacopeia, Shennong’s Materia Medica. Volatile oils, lignans, fatty acids, flavonoids, and nitrogen-containing compounds are the main ARR components. Previous pharmacological studies have shown that ARR exerts beneficial effects in humans for treating headaches, toothaches, and several inflammatory diseases by dispelling wind and cold, alleviating pain, and eliminating phlegm. However, “the dosage of ARR should not exceed one coin (approximately 3.75 grams)”, as stated in Shizhen Li’s Compendium of Materia, emphasized the considerable ARR toxicity and significantly constrained its clinical application. This review aimed to consolidate recent advancements in the understanding of the toxic ARR components. Additionally, we provide an overview of the hepatotoxicity, genotoxicity, neurotoxicity, and pulmonary toxicity of ARR and discuss the underlying molecular mechanisms. This study reviews the limitations of current studies and enhances our understanding of the toxic effects of ARR from the perspective of its toxic components and mechanisms, thereby providing a theoretical basis for the rational clinical practice of ARR-based medications.

Single-Scan Heteronuclear 13C-15N J-Coupling NMR Observations Enhanced by Dissolution Dynamic Nuclear Polarization.

Heteronuclear 13C-15N couplings were measured in single-scan nuclear magnetic resonance (NMR) experiments for a variety of nitrogen-containing chemical compounds with varied structural characteristics, by using a one-dimensional (1D) 13C-15N multiple-quantum (MQ)-filtered experiment. Sensitivity limitations of the MQ filtering were overcome by the combined use of 15N labeling and dissolution dynamic nuclear polarization (dDNP), performed at cryogenic conditions and followed by quick and optimized sample melting and transfer procedures. Coupling information could thus be obtained from nucleotide bases, amino acids, urea, and aliphatic and aromatic amides, including the measurement of relatively small J-couplings directly from the 1D filtered spectra. This experiment could pave the way for NMR-based analytical applications that investigate structural and stereochemical insights into nitrogen-containing compounds, including dipeptides and proteins, while relying on heteronuclear couplings and nuclear hyperpolarization.

Numerical study on soot formation in ammonia/ethylene laminar counterflow diffusion flame

The ammonia addition can significantly inhibit soot formation in hydrocarbon fuel flames. However due to the complexity of the interaction between nitrogen and hydrocarbon, the inhibiting effect of NH3 addition on soot formation has not been fully understood yet. In this study, a mechanism is constructed through mechanism comparison, reduction and merging. The constructed mechanism includes ammonia, polycyclic aromatic hydrocarbons (PAHs) and nitrogen-containing aromatic compounds (NACs) sub-chemistry. Then the constructed mechanism is coupled with a soot model to conduct a series of simulations of ammonia/ethylene laminar counterflow flames with various ammonia doping ratios. The results show that the constructed model can reproduce the suppression effect of ammonia addition on soot formation well. To explain the chemical inhibiting effect, the rate of production (ROP) and reaction pathway are analyzed. It can be concluded that the main formation pathway of benzene is C2H4 → C2H3 → C2H2 → C3H3 → A1. The decomposition of ammonia consumes H radical which is necessary for the conversion of C2H4 to C2H3, leading to a decrease in the reaction rates along the benzene formation pathway. Moreover, the N-containing species react with the small hydrocarbon molecules/radicals to form hydrogen cyanide (HCN), in which the reaction between C2H2 and N radical is the largest contributor. Compared to the reactions between C1-C2 species and nitrogen-containing species, the reactions between C3 species and nitrogen-containing species contribute less to the chemical effect of NH3 addition. All these reactions reduce the carbon flux of the benzene formation path. In addition, the impact of reactions between HCN and aromatic hydrocarbons which produce NACs is also investigated. The reactions of HCN addition to benzene and naphthalene compete with the C2H2 addition reactions, resulting in a slightly enhanced inhibiting effect of ammonia addition on soot formation.

Hydrogen Sulfide Increases Drought Tolerance by Modulating Carbon and Nitrogen Metabolism in Foxtail Millet Seedlings

Hydrogen sulfide (H2S), a novel gas signaling molecule, has been shown to enhance plant resistance to various abiotic stresses. Here, we investigated the effect of sodium hydrosulfide (NaHS, a H2S donor) on the growth, photosynthetic parameters, and enzyme activities related to carbon and nitrogen metabolism, as well as the levels of carbohydrates and nitrogen metabolites in foxtail millet seedlings subjected to drought stress conditions in pots. The findings revealed that drought stress led to a significant 41.2% decline in the total dry weight (DW) after 12 days of treatment, whereas plants treated with NaHS showed a lesser reduction of 18.7% in total DW. Under drought stress, exogenous NaHS was found to enhance carbon metabolism in foxtail millet seedlings by significantly enhancing photosynthetic capacity, starch, and sucrose content. Additionally, exogenous NaHS was observed to improve nitrogen metabolism by substantially increasing soluble protein content, nitrogen assimilate activity, and synthesis of nitrogen-containing compounds in foxtail millet seedlings. In summary, the exogenous application of NaHS stimulated seedling growth and enhanced drought resistance in foxtail millet by modulating carbon and nitrogen metabolism processes affected by drought stress.

One-pot synthesis of quinazolinone heterocyclic compounds using functionalized SBA-15 with natural material ellagic acid as a novel nanocatalyst

The nanoporous compound SBA-15 was functionalized using (3-aminopropyl)trimethoxysilane (APTES). Then the obtained product was modified with ellagic acid (ELA), a bioactive polyphenolic compound. The structure of the prepared nanoporous composition SBA-15@ELA was extensively characterized and confirmed by various techniques, such as Fourier-transform infrared (FT-IR) spectroscopy, Energy dispersive X-ray (EDX) elemental analysis, scanning electron microscopy (SEM), thermogravimetric analysis (TGA), X-ray diffraction (XRD), transmission electron microscopy (TEM) and N2 adsorption–desorption isotherms (BET). The novel, recoverable, heterogenous SBA-15@ELA nanoporous compound was used to investigate its catalytic effect in the synthesis of 4-oxo-quinazoline derivatives (19 examples) with high yields (78–96%), as an important class of nitrogen-containing heterocyclic compounds. The use of an inexpensive mesoporous catalyst with a high surface area, along with easy recovery by simple filtration are among the advantages of this catalysis research work. The catalyst has been used in at least 6 consecutive runs without a significant loss of its activity.

Catalysts for C-N coupling in urea electrosynthesis under ambient conditions from carbon dioxide and nitrogenous species.

Urea is an indispensable nitrogen-containing organic compound in modern human life. However, the current industrial synthesis of urea involves ammonia, which is produced through the Haber-Bosch process under harsh reaction conditions, causing huge energy consumption and heavy environmental pollution. Electrochemical reduction of carbon dioxide (CO2) and nitrogenous species (N2, NOx- and NO) have achieved significant progress, offering a promising approach for the electrochemical C-N coupling to produce urea under ambient conditions. Urea synthesis driven by renewable electricity represents a suitable alternative to the traditional process, contributing to the goal of carbon neutrality and nitrogen cycles. However, challenges such as low yield rate, poor selectivity and unveiled reaction mechanisms still need to be addressed. This review provides a summary of the latest catalysts utilized in urea electrosynthesis, aiming to provide guidance and prospects for the development of high-performance catalysts.

Development of nickel vanadium-impregnated activated carbon nanocomposites for electrocatalytic conversion of furfural into fuels

Abstract Furfural, derived from biomass, is crucial for achieving carbon neutrality through biomass utilization. It can be converted into furfuryl alcohol and other valuable components used in the chemical industry. Electrochemical methods offer improved selectivity in the conversion of furfural under mild conditions compared to traditional hydrogenation. This study investigates the electrocatalytic conversion of furfural using a hydrothermally synthesized nickel-vanadium-impregnated activated carbon (NiV/AC) catalyst. The developed catalysts were characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS) and X-ray photoelectron spectroscopy (XPS). The as-developed catalyst was used to synthesize electrodes for the electrochemical conversion of furfural. The behavior was investigated using electrochemical impedance spectroscopy (EIS) and linear sweep voltammetry (LSV). The study optimized the Ni:V ratio, applied voltages, electrolyte molarity and reaction time and found that a Ni:V ratio of 1:1 resulted in maximum furfural conversion. The Ag/AgCl cathode at -0.9 V showed a low reaction rate, thus requiring higher voltages for efficient conversion. LC-UV-ESI MS analysis of the cathode half-reaction revealed the formation of a nitrogen-containing compound, likely stemming from the reaction between furfural and acetonitrile under the influence of the catalyst. This study demonstrates the effectiveness of NiV/AC catalysts in the electrocatalytic conversion of furfural, with a conversion rate of 90% and a faradaic efficiency of around 30% at -1.3 V. Furthermore, a plausible reaction mechanism was proposed.

Visible-light harvesting SrTiO3 solid solutions for photocatalytic hydrogen evolution from water.

The fabrication of solid solutions represents a compelling approach to modulating the physicochemical properties of materials. In this study, we achieved the successful synthesis of solid solutions comprising SrTiO3 and SrTaO2N (denoted as (SrTiO3)1-x-(SrTaO2N)x, 0 ≤ x ≤ 1) using the magnesium powder-assisted nitridation method. The absorption edge of (SrTiO3)1-x-(SrTaO2N)x is tunable from 500 to 600 nm. The conduction band minimum (CBM) of (SrTiO3)1-x-(SrTaO2N)x comprises the Ti 3d orbitals and the Ta 5d orbitals, while the valence band maximum (VBM) consists of the O 2p and N 2p orbitals. The microstructure of the (SrTiO3)1-x‑(SrTaO2N)x consists of small nanoparticles, exhibiting a larger specific surface area than the parent compounds of SrTiO3 and SrTaO2N. In the photocatalytic hydrogen evolution reaction (HER) with sacrificial reagents, the activity of solid solutions is notably superior to that of nitrogen-doped SrTiO3 and SrTaO2N. This superiority is mainly attributed to its broad light absorption range and high charge separation efficiency, which indicates its potential as a promising photocatalytic material. Moreover, the magnesium powder-assisted nitridation method exhibits obvious advantages for the synthesis of oxynitrides and bears instructional significance for the synthesis of other nitrogen-containing compounds and even sulfur-containing compounds.

Insights into heavy components evolution in the condensed volatiles from amino acids pyrolysis

Heavy components, comprised of molecules with a substantial molecular mass, are essential constituents within volatiles. Within these molecules, nitrogen-containing compounds have a tendency to undergo transformation into coke during thermal treatment, exerting a substantial impact on the efficient and secure utilization of biomass. Three amino acids- alanine with an aliphatic structure, phenylalanine with additional aromatic features, and tryptophan with an extra heterocyclic ring were selected as model compounds, individually subjected to pyrolysis within the temperature range of 450 to 650 °C. The evolution of heavy components and the associated reaction mechanisms were comprehensively explored through extensive characterization and network analysis. The results showed that alanine transformed into heavy components mainly through dehydration followed by dissociation of CH2 and CH. In contrast, phenylalanine and tryptophan tended to undergo fragmentation into C8H7N· and C12H10N2· derivatives, subsequently recombining to form heavy molecules. As the temperature increased, heavy components in alanine-derived volatiles monotonously decreased due to elimination reactions and the breaking of C–C bonds. Conversely, heavy components in phenylalanine and tryptophan initially increased and then decreased due to the enhanced cracked fragments, along with the competitive relationship between aromatization and polymerization reactions. For all three amino acids, there is a positive correlation among the average mass of heavy components, tar yield, and the intensity of permanent free radicals in the char. This implies that we may rapidly predict the evolutionary patterns of heavy components and tar through free radical detection. HCN dissociation is mathematically identified as a pivotal reaction in heavy component evolution, irrespective of amino acid type, possibly unveiling an important pathway for NOx formation. This study shows substantial theoretical significance for the eco-friendly and efficient conversion of nitrogen-rich biomass.

Preparation of low-nitrogen bio-oil from co-pyrolysis of waste tobacco stem and corn stalk: Product characteristics and denitrogenation mechanism

Substances such as nicotine and tobacco proteins in waste tobacco stem (TS) could result in higher content of nitrogenous compounds and lower calorific value and cleanness in the pyrolysis bio-oil. This study focused on the co-pyrolysis of TS with corn stalk (CS) to investigate the product characteristics and denitrogenation effects during the co-pyrolysis process. The results indicated that co-pyrolysis of TS with CS remarkably reduced nitrogenous compounds from 43.75% to 6.42% in bio-oil, at a 1:1 blending ratio of TS and CS. With the addition of CS, the most of nitrogen-containing and oxygen-containing compounds were removed from bio-oil. Co-pyrolysis of TS with three main components in biomass was also conducted. It revealed that the lignin component in the CS played a key role in bio-oil denitrogenation during co-pyrolysis. When the blending ratio of TS and lignin was 1:1, 39.45% of nitrogenous compounds in the bio-oil was reduced. Lignin promoted the amino migrates from bio-oil to gas and char.

Recent Progress in the Synthesis and Biological Assessment of Benzimidazole-1,2,3-Triazole Hybrids

Abstract: In recent times, many research groups have focused their attention on nitrogencontaining heterocyclic compounds with the aim of gaining a deeper understanding of their biological characteristics. Among them, molecules based on 1,2,3-triazole and benzimidazole have exhibited diverse biological applications and are present in many drug molecules. The purpose of this review is to describe various benzimidazole-1,2,3-triazole hybrids and to provide a comprehensive evaluation of their biological properties. The compounds discussed in this study have been synthesized through a Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction between diverse azides and alkynes, utilizing a 1,2,3-triazole scaffold as a linkage between two connecting groups. The synthesis of several benzimidazole-1,2,3- triazole hybrids is covered in this review, along with a biological assessment of their anticancer, antiproliferative, antitubercular, antibacterial, antidepressant, and other activities. Moreover, in our opinion, this review may be useful for the development of various medicinally significant molecules.

Theoretical Revelation of HNCO Formation during Coal Pyrolysis: Mechanism, Formation Pathway and DFT Calculation

ABSTRACT Pyridine is one of the main nitrogen-containing compounds that produce NOx precursors (HNCO, HCN, NH3) in coal during pyrolysis, which can be converted into 2-pyridone (2-Py) in the presence of H2O. HNCO is a NOx precursor during coal and coal tar pyrolysis. In this study, the possible paths for the pyrolysis of 2-pyridone to generate HNCO and HCN were studied using density functional theory (DFT). This was the first theoretical revelation of the source of HNCO generation during coal pyrolysis. At the same time, the formation path of HCN was also calculated and compared with the formation of HNCO. Through the transition state theory analysis, the behavior characteristics of NOx precursors produced during the pyrolysis of 2-pyridone were theoretically explained.

Sustainable biorefining: Hydrothermal liquefaction of diatom biomass for bio-crude and nano-biosilica recovery

Diatom, a unique species of microalgae is a highly promising resource for the production of valuable bio-crude and silica nanomaterial. However, the complex nature of diatom cell structure presents significant downstream processing challenges and leads to inefficient bio-product recovery. To overcome this challenge, this study aimed to develop a one-step approach for the valorization of Denticula sp. dominated diatom consortium using hydrothermal liquefaction (HTL) process with the recovery of three major products. The first output, referred to as biocrude, constituted 22% of the total yield, consisting of 9.5% unbound bio-crude and 12.5% cell wall-bound organic fraction. The bio-crude consisted primarily of oxidized and desirable organic compounds like alcohols (24.4%), long-chain saturated hydrocarbons (23.6%), and esters (17.6%), with only a few undesirable nitrogen-containing compounds (18.9%). The second resultant product comprised nanoporous bio-silica structures, yielding 56%. These silica structures exhibited enhanced quality in comparison to the conventional thermal extraction technique employed for their retrieval and were found to be three-dimensional, highly porous, intact silica structures with low trace elements and a high surface area (53.7 m2 g−1). The third acquired product, the aqueous fraction, was observed to possess elevated levels of nitrate-nitrogen (440 mg L−1) and total dissolved phosphate (975 mg L−1). Overall, the study highlights the potential of HTL as an efficient diatom downstream processing method that allows for the complete valorization of intermediates, resulting in a sustainable biomass conversion and product recovery technology.

Dehydrated mycelia (Cordyceps militaris, Grifola frondosa, Hericium erinaceus and Laricifomes officinalis) as Novel Foods: A comprehensive NMR study

Several medicinal mushrooms have been approved as European Novel Foods or have the potential to become Novel Foods. However, their chemical characterization is limited, being mainly focused on specific compounds.Here, the dehydrated mycelia (isolated from sporophores collected in Italy) of Grifola frondosa, Hericium erinaceus, recently defined as Novel Foods, and Cordyceps militaris and Laricifomes officinalis, with potential Novel Food use, were analyzed by NMR methodology to define their metabolite and nutritional profile. Amino acids and derivatives, sugars and polyols, organic acids, fatty acids, lipid polar moieties, nitrogen-containing compounds were identified and quantified in hydroalcoholic and organic extracts.C. militaris showed a high amount of glutamate, citrate and mannitol, also involved in mushroom taste, being the only species presenting tri-unsaturated fatty acids. L. officinalis was characterized by the highest amount of TAA and EAA, and the lowest sugars and polyols content. G. frondosa and H. erinaceus were characterized by high amounts of trehalose (13–14 % of dried weight).Each dehydrated mycelia potentially represents an innovative food matrix alone, for culinary, nutritional and nutraceutical needs, or mixed together to obtain new products. Moreover, these mycelia can be of interest as sources of isolated bioactive compounds for supplements with particular nutritional functions.

Carbonylative synthesis and functionalization of indoles.

Carbonylation processes have become widely recognized as a versatile, convenient, and low-cost method for the synthesis of high-value compounds. Given the great importance of heterocyclic compounds, the carbonylative approach has become increasingly important for their synthesis. In this mini-review, as a class of benzo-fused nitrogen-containing heterocyclic compounds, we summarized and discussed the recent achievements on the synthesis and functionalization of indole derivatives via carbonylative approaches.

GC-IMS-Based Volatile Characteristic Analysis of Hypsizygus marmoreus Dried by Different Methods.

Gas chromatography-ion mobility spectroscopy (GC-IMS) was used to analyze the volatile components in dried Hypsizygus marmoreus of different drying methods, including hot air drying (HAD), heat pump drying (HPD), heated freeze-drying (HFD), and unheated freeze-drying (UFD). A total of 116 signal peaks corresponding to 96 volatile compounds were identified, including 25 esters, 24 aldehydes, 23 alcohols, 13 ketones, 10 heterocyclic compounds, 8 carboxylic acids, 7 terpenes, 3 sulfur-containing compounds, 2 nitrogen-containing compounds, and 1 aromatic hydrocarbon. The total content of volatile compounds in H. marmoreus dried by the four methods, from highest to lowest, was as follows: HAD, HPD, HFD, and UFD. The main volatile compounds included carboxylic acids, alcohols, esters, and aldehydes. Comparing the peak intensities of volatile compounds in dried H. marmoreus using different drying methods, it was found that the synthesis of esters, aldehydes, and terpenes increased under hot drying methods such as HAD and HPD, while the synthesis of compounds containing sulfur and nitrogen increased under freeze-drying methods such as HFD and UFD. Nine common key characteristic flavor compounds of dried H. marmoreus were screened using relative odor activity values (ROAV > 1), including ethyl 3-methylbutanoate, acetic acid, 2-methylbutanal, propanal, methyl 2-propenyl sulfate, trimethylamine, 3-octanone, acetaldehide, and thiophene. In the odor description of volatile compounds with ROAV > 0.1, it was found that important flavor components such as trimethylamine, 3-octanone, (E)-2-octenal, and dimethyl disulfide are related to the aroma of seafood. Their ROAV order is HFD > UFD > HPD > HAD, indicating that H. marmoreus using the HFD method have the strongest seafood flavor. The research findings provide theoretical guidance for selecting drying methods and refining the processing of H. marmoreus.

The effect of non-Saccharomyces yeasts on biogenic amines in Sauvignon Blanc wine and Gewürztraminer wine

Biogenic amine (BA) is a class of nitrogen-containing small molecular organic compounds with biological activity. Excessive BAs in wine affect flavor and quality of wine and are hazardous to human health. However, little attention has been paid to the effect of non-Saccharomyces yeasts and Saccharomyces cerevisiae mixed fermentation on BAs in white wine. The effect of mixed fermentation on BAs and amino acids in wine was investigated using two white grapes of Sauvignon Blanc and Gewürztraminer. Higher levels of total amino acids and BAs in Gewürztraminer wine compared to Sauvignon Blanc wine may be due to different grape varieties. Mixed fermentation did not influence BA profiles in Sauvignon Blanc wine, while it increased total BAs content. VL3 (VL) fermented wine has 33.7% less BAs content than EC1118 (EC) single-strain fermented wine. Similar phenomenon was found in Gewürztraminer wine produced by different fermentation combinations except that cadaverine was only detected in wine produced by Hanseniaspora uvarum participated in mixed fermentations. Principal coordinate analysis (PCoA) and permutational multivariate analysis of variance (PERMANOVA) revealed that the effects on BAs were related to grape varieties and yeast species in white wine. Ethanolamine, tryptamine, isoamylamine and histamine content in wine were related to grape varieties. Collectively, mixed fermentation increased BAs content in Sauvignon Blanc and Gewürztraminer wine. The content of BAs in wine fermented by VL single-strain fermentation was lower than that fermented by EC single-strain fermentation, which is more suitable for the winemaking of white wine.

Mesoporous CuMn2O4 nanoframework as an efficient catalyst for the synthesis of benzimidazole derivatives through air oxidative coupling in water

Mixed-metal oxide (MMO) CuMn2O4 nanoframework with a mesoporous structure was synthesized. The advantages of this mesoporous MMO are its large specific surface area, uniform pore size, and various metal valence states. MMO CuMn2O4 nanoframework showed efficient catalytic activity in the oxidative coupling of 2-amino/hydroxy/mercaptoanilines with various alcohols in the preparation of benzimidazoles, benzoxazoles, and benzothiazoles using water as the sole solvent in high yields. The efficient catalytic activity is mainly attributed to large specific surface area, increased number of active sites, solvent reorganization between the pores of mesoporous CuMn2O4 nanoframework, and the various electronic states of the copper and manganese ions (Cu+, Cu2+, Mn3+, Mn4+) due to the Jahn-Teller effect. This research provides new insights into improving the catalytic performance of catalyst for the synthesis of nitrogen-containing five-membered ring compounds.