Green and Sustainable Syntheses of Quinoxaline Derivatives via Nicotinamide Catalysis in Water

Abstract

The synthesis of medicinally significant quinoxaline derivatives, utilizing quinoxaline as a heterocyclic scaffold, was efficiently achieved with catalytic amounts of nicotinamide, one of the B-vitamins and a cost-effective, nontoxic, and readily available catalyst, in water, yielding excellent results with merely 10 mol% catalyst loading. A systematic examination of the reaction parameters, including solvent and catalyst loading, was conducted to optimize the yield. Various aromatic and aliphatic 1,2-diketones and 1,2-diamines, such as substituted phenylenediamines and heterocyclic diamines, were subjected to nicotinamide-catalyzed condensation, producing 20 quinoxaline derivatives in high yields (85–96%). The reaction products were characterized by ¹H and ¹³C NMR, FT-IR, and mass spectral analyses. This green and sustainable method, utilizing water as a solvent, highlights quinoxaline’s potential as a valuable scaffold in the medicinal chemistry of small-molecule drugs for diverse therapeutic applications.

Keywords

Nicotinamide - Green chemistry - Catalytic efficiency - Water solvent

Significance

The present study reports an eco-friendly, safe, and economic strategy for synthesizing quinoxaline derivatives, which make up a promising heterocyclic scaffold for multiple applications, by using nicotinamide, a vitamin B₃-based, nontoxic, and water-soluble organocatalyst. The developed process avoids hazardous solvents, strong acids, and costly reagents, delivering high yields under mild, energy-efficient conditions. It promotes sustainable organic synthesis by reducing waste, improving safety, and supporting greener scientific and industrial practices.

1

Introduction

Quinoxaline (benzopyrazine) is a medicinally important, yet relatively less-explored heterocyclic scaffold, compared to the closely related quinazoline substructure. The recent surge in literature reports on the synthetic methodologies and pharmacological properties of quinoxaline derivatives is a testament of the renewed interest in this uniquely placed bicyclic heterocycle.[1] [2] [3] [4] [5] [6] It is a weakly basic aromatic heterocycle containing two N atoms at the 1,4 disposition, fused with a carbocyclic aromatic heterocycle.[7] [8] [9] [10] It is also a part of the tricyclic system in vitamin B2, i.e., riboflavin ([Chart 1]). Quinoxalines’ abundant bioactivity profiles have garnered considerable interest in its medicinal importance ([Chart 1]). Derivatives of quinoxaline have demonstrated antimicrobial, antimalarial, antifungal, antituberculous, antiviral, anticancer, antidepressant, and related activities.[11] [12] [13] [14] These are also used in organic dyes. Various synthetic methodologies for quinoxaline synthesis have been reported in the recent literature, based on environment-friendly, green strategies.[15] [16] [17] [18] [19] [20] In synthetic methodologies, the reliance on regulatory processes and organic solvents presents significant green chemistry concerns. While water introduces certain challenges in organic synthesis, we promote its use as a solvent for its safety, environmental benefits, and cost-effectiveness.[19]

Fig. 1 Effect of catalyst loading on reaction yield. Reaction Conditions: 1,2-diketone (1.0 mmol), 1,2-diamine (1.0 mmol), H₂O, Time: 0.5 h, RT.

Chart 1 Biological importance of some quinoxalines.

Previous literature reported on various strategies for quinoxaline synthesis using varied metal and organocatalysts ([Table 1] provided in supplementary information) such as Pd(OAc)_2, [20] RuCl₂-(PPh₃)₃-2,2,6,6 tetramethylpiperidine-1-oxyl (TEMPO),[20] MnO₂,[21] Al₂O₃-ZrO₂,[22] CuSO₄·5H₂O,[23] zirconium(IV)-modified silica gel acetic acid,[24] nanocrystalline CuO,[25] cerium(IV) ammonium nitrate iodine,[26] gallium (III) triflate,[27] montmorillonite K10,[28] and ionic liquids such as N,N,N-trimethyl-N-propanesulfonic acid ammonium hydrogen sulfate ([TMPSA]. HSO₄),[29] Nano-TiO₂,[30] sulfated TiO₂,[31] sulfamic acid/MeOH,[32] silica bonded S-sulfonic,[33] and iron-exchanged molybdophosphoric acid.[34] The demand for metal-free and nonhazardous organocatalytic reaction conditions in green technology has driven the development of various environment-friendly approaches. Among these, replacing hazardous inorganic acid catalysts like sulfuric and hydrochloric acids with reusable solid acids and performing reactions at room temperature to avoid media heating remains essential.[35] [36] [37] [38] [39] [40] The use of solid acids in organic transformations plays a crucial role, offering numerous advantages such as ease of handling, reduced plant corrosion, and more environmentally safe waste disposal practices.[41] [42] [43] [44]

Table 1 Optimization of catalyst loading and solvents.

Entry	Catalyst mol% loading	Solvent	Temperature (°C)	Time (h)	% Yielda
1	0	H2O	RT	24	bNR
2	2.5	H2O	RT	04	55
3	5	H2O	RT	01	75
4	10	H2O	RT	0.25	96
5	15	H2O	RT	0.30	95
6	10	EtOH	RT	0.25	94
7	10	IPA	RT	0.35	90
8	10	Toluene	RT	01	85
9	10	DCM	RT	0.30	89
10	10	Acetone	RT	02	82
11	10	n-Hexane	RT	1.5	80
12	10	MeOH	RT	0.25	93
13	10	EtOH:water (1:1)	RT	0.30	92
14	10	H2O	100 °C	0.5	69

^aIsolated yield.

^bNR: Not reported; Substrate: 1,2-diketone (1.0 mmol), 1,2-diamine (1.0 mmol).

While many of these methods offer individual synthetic advantages, they often suffer from limitations such as the need for toxic organic solvents, prolonged reaction times, anhydrous conditions, exclusive or corrosive reagents, strong acids, potent oxidants, toxic or costly catalysts, harsh reaction conditions, and tedious workup procedure. Therefore, developing a safe, environmentally friendly, mild, efficient, and high-yielding method employing cost-effective and green catalysts for quinoxaline synthesis remains highly desirable.[45]

In this invention, we have developed a new nicotinamide-catalyzed green synthesis method for quinoxaline derivatives. This environmentally friendly procedure employs nicotinamide as a green organocatalyst and water as a reaction medium, representing the first use of nicotinamide as a catalyst for quinoxaline synthesis. This method enables rapid synthesis under ambient conditions and affordable excellent yields without the use of toxic and corrosive reagents. Our approach is safer for analysts, more convenient than the previous method, and allows for higher yield reactions with shorter reaction times and milder temperatures. It also produces no pollution. These characteristics align with recent developments reported for the safer and more effecient quinoxaline synthesis methods. In the present study, we have adopted and further advanced this concept through a nicotinamide-catalyzed green synthesis approach, which offers several advantages, including high yields, short reaction times, affordability, and adherence to green chemistry principles.[46]

The objectives of the present study are to develop an environmentally-benign and cost-effective catalytic system for quinoxaline synthesis, optimize the reaction conditions for maximum efficiency under aqueous medium, and evaluate the substrate scope to establish the versatility of proposed method.

2

Materials and Methods

2.1

General

All the laboratory/analytical-grade chemicals, solvents, and reagents were procured from reputable suppliers, including Merck KGaA, Darmstadt, Germany, and AVRA Laboratories, India. These materials were used directly without further purification. Thin-layer chromatography (TLC) was performed on Merck TLC Silica gel 60 F₂₅₄ and visualized under UV light at 254 nm for preliminary compound separation and analysis. The structural characterization of the synthesized compounds was meticulously performed using nuclear magnetic resonance (NMR) spectroscopy, including both ¹H and ¹³C NMR and Fourier transform infrared (FTIR) spectroscopy. ¹H NMR spectra were routinely recorded on Agilent-500/54AR 500 MHz NMR spectrometer, with tetramethylsilane (TMS) as an internal standard, and the recorded spectra were processed using the evaluation version of MestReNova software (Note: CDCl₃ referenced at 7.26 ppm in ¹H NMR; DMSO-d ₆ referenced at 2.50 ppm in 1H NMR experiments.). The purity of the final compounds was assessed qualitatively from ¹H NMR spectra and TLC analyses. The FT-IR spectra were obtained on Jasco FT/IR-4600 spectrometer using the ATR sampling technique. Melting points were recorded using Veego Instruments, VMP-DS model, and capillary melting point apparatus (Mumbai, Maharashtra, India) and were uncorrected. Mass spectra (MS) were recorded on a Shimadzu 8040 LC MS/MS system (Japan) using electrospray ionization (ESI) mode.

2.2

General Procedure for the Synthesis of Quinoxaline Derivatives

A mixture of 1,2-diketone (1.0 mmol), 1,2-diamine (1.0 mmol), and nicotinamide (10 mol%) in water (5–10 mL) was stirred at room temperature (RT) ([Scheme 1]). The progress of the reaction was monitored using TLC. Water (10 mL) was added and stirred for 5 min. The product was precipitated and subsequently separated by filtration. The crude product was washed several times with water. After drying, the pure product was obtained.

Scheme 1 Synthesis of substituted quinoxalines (3) in water using nicotinamide as a homogeneous catalyst.

2.3

Synthesis of Quinoxaline (3a)

A mixture of glyoxal (1.0 mmol), o-phenylenediamine (1.0 mmol), and nicotinamide (10 mol%) in water (5–10 mL) was stirred at RT. The progress of the reaction was monitored using TLC. Water (10 mL) was added and stirred for 5 min. The precipitated product was subsequently separated by filtration. The crude product was washed several times with water and dried in oven at 60 °C for 2 h.

2.4

Characterization Data

Melting point: 30–32 °C; ¹H NMR (500 MHz, CDCl₃) δ 8.81 (s, 2H), 8.08 (dd, J = 6.3, 3.5 Hz, 2H), 7.74 (dd, J = 6.4, 3.4 Hz, 2H); ¹³C NMR (101 MHz, CDCl₃) δ 144.93, 142.97, 130.12, 129.45; IR (ATR, cm⁻¹): 2979, 2891, 1573, 1385, 1156, 1085, 950, 825, 751, 419; HRMS (ESI-TOF) m/z: [M + H]⁺ calcd for C₈H₆N₂: 130.05; found: 131.25.

2.5

Synthesis of 6-Nitroquinoxaline (3b)

The compound 3b was synthesized using similar procedure as 3a using glyoxal and 4-nitro-o-phenylenediamine. Melting point: 172–174 °C; ¹H NMR (500 MHz, CDCl₃) δ 9.04 (d, J = 7.0 Hz, 3H), 9.04 (d, J = 7.0 Hz, 3H), 8.57 (d, J = 8.5 Hz, 1H), 8.57 (d, J = 8.5 Hz, 1H), 8.30 (d, J = 9.1 Hz, 1H), 8.30 (d, J = 9.1 Hz, 1H); ¹³C NMR (101 MHz, CDCl₃) δ 147.95, 147.67, 147.04, 145.33, 141.91, 131.37, 126.01, 123.51; IR (ATR, cm⁻¹):1635, 1485, 1307, 980, 784; HRMS (ESI-TOF) m/z: [M + H]⁺ calcd for C₈H₅N₃O₂: 175.14; found: 176.15.

3

Results and Discussion

Quinoxaline derivatives reported in the present study were prepared using nicotinamide as a homogeneous catalyst for the condensation reaction involving o-phenylenediamine and glyoxal derivatives in water (as a solvent). Nicotinamide, a white to off-white crystalline powder, is highly soluble in water (1 g/mL at 25 °C), and slightly soluble in organic solvents such as EtOH and glycerin. It is stable in the pH range of 3–7.5 and is relatively inert under mild conditions. The pK _a of pyridine N is ~3.3 (relatively weakly basic). It is relatively nontoxic at standard dosages and is environmentally benign. Nicotinamide has been used in several applications such as cocrystal formation with active pharmaceutical ingredients (APIs), particularly for improving aqueous solubility[47] owing to intermolecular H-bonding with corresponding functional groups in the APIs (mediated via pyridine N as well as conformationally flexible amide group). We reasoned that the unique chemical property set of nicotinamide could catalyze condensation reactions between 1,2-diamines and 1,2-diketones, yielding substituted quinoxalines under mild conditions. Our recently published study used l-arabinose as yet another mild, environmentally benign homogeneous catalyst in water:MeOH (1:1) as solvent system.[48] Under the optimized conditions, we obtained the product yields in a respectable range of 80–95%. All the synthesized derivatives were analyzed by ¹H, ¹³C NMR, FT-IR, and MS techniques.

Initial investigations were focused on exploring the suitability of nicotinamide as a catalyst under varied reaction conditions for synthesizing the quinoxaline derivatives. At the outset, equimolar combination of (un)substituted o-phenylenediamines, a typical substrate class, and glyoxal was used. The effect of the catalyst loading on reaction time and product yields was measured and compared with the corresponding results without the catalyst. Under catalyst-free conditions, the reaction proceeded at 100 °C, but with great difficulty, as seen from the longer time and poor yield. Increasing the catalyst loading resulted in increased product yield with a significant reduction in reaction time. ([Table 1] and [Fig. 1]) The catalyst loading beyond 10 mol% could result in no benefit. Hence, 10 mol% catalyst loading was considered optimal for further studies.

Next, the investigations were focused on selecting a suitable solvent for the condensation reaction. We tried solvents such as toluene, ethanol, methanol, n-hexane, acetone, isopropyl alcohol, ethanol, and methyl dichloride. Surprisingly, relatively better yields were obtained in water ([Table 2]) at RT. The solvent polarity had a direct impact on the reaction time and yield, i.e., protic solvents led to higher yield and lesser reaction time, with subtle differences among water, methanol, IPA as well as the EtOH:Water (1:1) mixture ([Table 2]). Nicotinamide played a crucial role in the condensation reaction; without the catalyst, reaction yield was poor despite the longer reaction time. Increasing the temperature to 100 °C led to completion of reaction after relatively longer reaction time ([Table 1], entry 14).

Table 2 Catalytic efficiency of amides under ambient conditions.

Entry	Catalyst	Structure	Temperature (°C)	Time (min)	aYield (%)
1	Nicotinic acid		RT	40	95
2	Benzylamide		RT	60	89
3	N,N-dimethylnicotinamide		RT	35	90
4	Acetamide		RT	60	85
5	Nicotinamide		RT	15	96

^a Yield (%): isolated yield.

Following the optimization of reaction conditions, wherein a clean condensation of 1,2 diamine and 1,2-dicarbonyl reactants resulted in a pure product, with no side-reaction(s) or by-products, various substituted 1,2-diamines and 1,2-dicarbonyl compounds were employed for the condensation reactions and the electronic effects of the substituents on either of the reactants on the overall outcome of the reaction were studied. The observed yields indicated a slight difference between derivatives bearing electron-donating and electron-withdrawing groups, on either of the reagents ([Chart 2], Table 3). Compounds comprising aromatic 1,2 diamine and aliphatic diketone scaffolds (3a to 3l) exhibited slightly higher yields (90–92%) for derivatives with electron-donating groups on the diamine, most likely due to its enhanced nucleophilicity. Conversely, compounds with electron-withdrawing substituents showed slightly lower yields (87–93%), suggesting that these groups may reduce reactivity. Compounds 3m to 3r, comprising both the aromatic diamine and the diketone scaffolds, displayed yield variations depending on the electronic nature of their substituents. Specifically, derivatives with electron-withdrawing groups on either the diamine or the diketone part exhibited a slight decrease in yield compared to those with electron-donating groups, which achieved higher yields. Compounds 3s (aliphatic diamine and aromatic diketone) and 3v (heterocyclic diamine and aromatic diketone) achieved comparable yields, indicating that the electronic nature of the substituents played a consistent role in yield modulation regardless of the nature of the core structure. Overall, the yields of all derivatives were observed within the range of 85–95% on an isolation basis.

Chart 2 Substrate scope for quinoxaline synthesis.

The synthesis of 2,3-disubstituted quinoxalines proceeded via a well-defined proposed mechanistic pathway involving the transient activation of one of the –C=O groups of the 1,2 diketone via H-bonding (I, [Fig. 2]), contributed by nicotinamide catalyst, rendering it more electrophilic and priming it for the ensuing nucleophilic attack. This led to tetrahedral Intermediate A, following the nucleophilic attack of one of the amino groups from the 1,2 diamine on the supposedly electrophilic carbonyl C (II, [Fig. 2]). Following this, the newly formed tertiary alcohol underwent sequential double protonation (water as the proton source), thereby promoting dehydration, leading to the generation of Intermediate B. Next, the remaining carbonyl group in Intermediate B is also activated in a similar fashion (III), making it susceptible to an intramolecular nucleophilic attack by the second amino group from the 1,2 diamine (IV). The resulting cyclic tetrahedral Intermediate C similarly underwent sequential dehydration, generating the final quinoxaline product, a 2,3-disubstituted quinoxaline (3). As the study involved symmetrical 1,2-diketone molecules, the reaction pathway was predictable, with no regioisomeric concerns about the final product’s structure. However, when unsymmetrical 1,2-diketones are employed, different regioisomeric products are expected due to the possibility of two distinct nucleophilic attacks on the nonequivalent carbonyl groups. Such study will be the subject matter for future work. The proton abstraction steps drawn are general acid/base-mediated proton relays, supplied by species that inevitably exist in the pot even when the bulk medium is neutral/slightly basic. H₂O (and (H₂O) _n ) is an efficient proton shuttle; transfers can occur through a 6–8-membered H-bonded ring without requiring any free mineral acid. Although the mixture is overall basic, each nucleophilic addition transiently generates ion pairs that can donate or accept a proton locally. Only a tiny fraction is needed to be protonated at any moment to relay H⁺. These species (and their conjugate bases) are amphiprotic and participate in intramolecular or paired proton transfers. We are not proposing bulk acid catalysis; proximate general acid/base catalysis that accompanies each elementary step has thus been used.

To assess the scalability of this reaction, a larger-scale experiment was conducted using a 1 g batch under optimal conditions. The product was successfully isolated with an impressive 96% yield without additional purification. This high yield and purity in the larger batch demonstrated the reaction’s scalability and efficiency, confirming its potential for practical use in larger-scale synthetic applications. Overall, the proposed mechanism for the nicotinamide-catalyzed synthesis of quinoxaline derivatives proceeds through several key steps ([Fig. 2]) involving nucleophilic addition at the carbonyl C, dehydration, and cyclization. Nicotinamide’s role was hypothesized to be crucial throughout this reaction, as its H-bonding capacity stabilized the key 1,2-diketone substrate, ensuing intermediates, and the transition states leading them, thereby reducing the activation energy and facilitating the reaction’s progression under mild conditions. The proposed catalytic pathway is highly selective, yielding quinoxaline derivatives with minimal or no side reactions, which underscored the efficiency and eco-friendliness of using nicotinamide as a catalyst in quinoxaline synthesis.

Fig. 2 Plausible reaction mechanism and the role of the catalyst, nicotinamide, leading to product 3a.

Intrigued by the superior performance of the nicotinamide catalyst, we evaluated the catalytic performance of various structurally related compounds, including nicotinic acid, benzamide, N,N-dimethylnicotinamide, acetamide, and compared with nicotinamide. All reactions were carried out under originally optimized mild, ambient conditions (RT) to assess the efficiency and potential of each catalyst in terms of reaction time and yield. Both nicotinic acid and N,N-dimethylnicotinamide showed strong catalytic potential, reaching yields of 95% and 90% in 40 and 35 min, respectively. Despite their structural differences, the similar performance of these two catalysts, even though the reaction time was longer, indicated that the catalytic efficiency might not solely depend on the functional group nature. Although benzamide and acetamide required longer reaction times (60 min each), they still achieved high yields of 89% and 85%, respectively.

[Table 2] summarizes the reaction times and yields for each catalyst evaluated. Notably, all catalysts produced high yields (85–96%) within short reaction times under ambient conditions, underscoring their catalytic effectiveness. Nicotinamide demonstrated the highest efficiency, achieving a 96% yield in 15 min. This remarkable activity, characterized by both rapid reaction and high yield, suggested that nicotinamide was particularly effective as a catalyst. The enhanced catalytic performance of nicotinamide may be attributed to its ability to engage in H-bonding interactions, with potential effect on substrate solubility in the aqueous environment (optimized reaction conditions). Additionally, the H-bonding may stabilize the involved transition state(s), facilitating the reaction pathway and reducing the activation energy.

4

Catalyst Recycling

[Fig. 3] illustrates the reusability of the nicotinamide catalyst under RT conditions in the water solvent. After completion of the reaction, an additional small amount of water was added to facilitate the separation of product. Since nicotinamide is water-soluble, the product precipitated out while the catalyst remained in the aqueous phase. The product was then filtered, and the filtrate was used for subsequent repeat reactions. The catalyst was reused in four subsequent reactions, showing no significant loss in catalytic activity, demonstrating its robustness and efficiency over multiple cycles. The presented process, thus, highlights the sustainability and cost-effectiveness of the catalyst system.

Fig. 3 Effect of catalyst recycling on overall % yield of the product 3a.

5

Conclusions

Overall, the presented work presents a clean, efficient, and environmentally friendly method for synthesizing quinoxaline derivatives using 1,2-diketones and 1,2-diamines across various substrates. The method employs the low-cost, readily available nicotinamide as a catalyst, operating effectively at room temperature with a high reaction rate and producing superior yields. A simple filtration technique allows for easy isolation of the product, enhancing both convenience and practicality. The use of water as a universal solvent not only minimizes environmental impact but also offers economic advantages, reinforcing the method’s alignment with green chemistry principles. This approach not only enables an effective catalytic system for quinoxaline synthesis but also holds promise for extending these benefits to broader chemical syntheses. Additionally, we have established the feasibility of using nicotinamide as a sustainable catalyst for quinoxaline synthesis, with the catalyst demonstrating excellent reusability through multiple cycles without significant loss of efficiency. This innovative approach, thus, lays the foundation for future applications in eco-friendly, cost-effective organic transformations, highlighting its potential in sustainable chemical manufacturing.

Contributorsʼ Statement

Sandip J. Detke: Data curation, Formal analysis, Investigation. Omkar C. Harasure: Investigation, Methodology. Sai Srinivas Ponugoti: Investigation. Shreerang V. Joshi: Investigation. Prashant Kharkar: Conceptualization, Data curation, Formal analysis, Methodology, Project administration.

Conflict of Interest

The authors declare that they have no conflict of interest.

Acknowledgement

The authors thank Prof. Aniruddha B. Pandit, Vice Chancellor, Institute of Chemical Technology, Mumbai for all the infrastructure support provided. No funding was received for the presented research work.

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Publication History

Received: 22 August 2025

Accepted after revision: 08 December 2025

Accepted Manuscript online:
09 December 2025

Article published online:
13 February 2026