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. 2025 Nov 14;10(46):56692–56700. doi: 10.1021/acsomega.5c09337

Mild and Green Methodology for NIS-Mediated Synthesis of Quinoxalines from o‑Phenylenediamines and Sulfoxonium Ylides at Room Temperature

Humaira Parveen †,*, Sayeed Mukhtar †, Mona O Albalawi ‡, Syed Khasim §, Mohmmad Younus Wani ∥
PMCID: PMC12658707  PMID: 41322567

Abstract

An efficient, mild, green, and metal-free protocol for the synthesis of quinoxaline from sulfoxonium ylides and o-phenylenediamines in the presence of N-iodosuccinimide (NIS) at room temperature has been developed. This operationally simple protocol avoids hazardous catalysts or oxidants, tolerates diverse functional groups, and delivers products in good to excellent yields with high atom economy. The scalable procedure holds promise for applications across pharmaceuticals, biotechnology, materials science, and agriculture, offering an efficient route to novel bioactive molecules and cost-effective drug discovery.

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1. Introduction

Quinoxaline is a renowned and significant class of nitrogen-containing heterocyclic compounds that display broad pharmaceutical and biological properties. Compounds possessing a quinoxaline framework display a wide range of biological and pharmaceutical activities, such as anti-HIV, anticancer, antileishmanial, antiproliferative, antitumor, etc. Moreover, the quinoxaline framework is also an active essential unit of numerous advanced functional materials, herbicides, antibiotics, fungicides, and pesticides.

Some illustrative examples of the quinoxaline moiety containing bioactive molecules are varenicline, quinacillin, chloroquinoxaline sulfonamide, brimonidine, BMS-345541, and XK-469 (Figure ).

1.

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Quinoxaline derivatives have various biological activities.

Because of these significant applications, various synthetic protocols have been developed to synthesize quinoxalines. − Among these protocols, reaction of ketones or alkynes with 1,2-diamines, condensation reaction of 1,2-diketones with 1,2-diamines, reaction of 1,2-diamines with phenacyl bromides, and oxidation of α-hydroxy ketones or vicinal diols with 1,2-diamines have broadly been employed (Scheme ). Additionally, cyclization of o-phenylenediamines was deliberated to achieve quinoxalines via the photochemical dimerization or metal/enzyme-catalyzed procedure. Nowadays, quinoxalines are also synthesized through the dehydrogenative coupling of alcohols and 1,2-diamines. Adhikari and co-workers reported a nickel-catalyzed production of quinoxalines through dehydrogenative coupling of vicinal diols and 1,2-diamines. Similarly, Balaraman et al. synthesized quinoxalines through a dehydrogenative coupling of vicinal diols and 1,2-diamines in the presence of the Mn­(I) catalyst.

1. Different Methodologies for the Synthesis of Quinoxalines.

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Recently, Paul and co-workers reported the synthesis of quinoxalines through a well-defined and phosphine-free Mn­(II)-catalyzed dehydrogenative coupling of vicinal diols and o-phenylenediamines. Quinoxalines were also synthesized through the hydrogen transfer reduction of nitroarenes. Darcel et al. reported the synthesis of quinoxalines through the hydrogen transfer reduction of nitroarenes with o-phenylenediamines. Recently, Chaubey et al. reported an elemental sulfur-mediated synthesis of quinoxalines. Although attractive in terms of simplicity, this method suffers from several drawbacks, including limited functional group tolerance, unpredictable reactivity arising from multiple sulfur-derived intermediates, and difficulties in purification due to residual sulfur species. Moreover, the scalability and reproducibility of sulfur-mediated protocols may be hampered by safety and waste management concerns. Saini et al. have developed an I2-mediated site-selective C–H functionalization strategy that enables the synthesis of p-amino-substituted unsymmetrical benzils and quinoxalines from sulfoxonium ylides and unprotected aniline derivatives. Their approach demonstrates good substrate compatibility and provides moderate to high yields through downstream transformations. Nevertheless, this methodology intrinsically relies on selective C–H bond activation, which often requires careful optimization of conditions and may pose challenges when extended to sterically hindered or electronically diverse substrates. Even though these are noteworthy methodologies for the production of quinoxalines, the progress of environmentally friendly and mild approaches are still anticipated because (1) precursors should be effortlessly prepared and readily available; (2) oxidants should be environmentally friendly air or molecular oxygen; and (3) extra consideration should be given to reduce the hazardous byproducts. Therefore, our NIS-mediated methodology offers a more direct, convenient, and sustainable route to quinoxalines from o-phenylenediamines and sulfoxonium ylides. Operating smoothly at room temperature, our protocol eliminates the need for C–H functionalization, instead leveraging electrophilic activation to promote rapid and clean cyclization. This not only enhances operational simplicity and reproducibility but also ensures cleaner reaction profiles, easier purification, and broader functional group tolerance. Importantly, the benign nature of the reaction conditions makes our strategy readily scalable and more industry-friendly, with potential advantages in terms of cost-effectiveness and environmental sustainability.

Sulfoxonium ylides play important roles in synthetic organic chemistry as chemical materials, pharmaceuticals, and significant building blocks in total synthesis. Moreover, sulfoxonium ylides are also recognized as alternative metallocarbene surrogates to diazo compounds. They display numerous common reactions such as Stevens and Wolff rearrangements, epoxidation, dimerization, insertion, aziridination, and cyclopropanation. Moreover, sulfoxonium ylides are commonly crystalline solids and more stable as compared to diazo compounds. They are easier to synthesize and have already been utilized in industrial scales because they do not employ the usage of potentially explosive compounds such as diazomethane, azides, and their derivatives. In the past few years, sulfoxonium ylides have resurfaced as a prevailing and adaptable synthetic tool for various organic transformations. In this regard, Baldwin and Mangion reported metal-catalyzed N–H insertion reactions in which β-ketosulfoxonium ylides were employed as diazo carbonyl surrogates. Synthesis of functionalized haloketones, synthesis of pyrroles and indoles, cross-coupling reactions, and the construction of C–X, C–N, C–O, and C–C bonds and naphthols are some recent examples which utilized β-ketosulfoxonium ylides as coupling partners. To the best of our knowledge, no mild and green methodology for the production of quinoxalines from sulfoxonium ylides and o-phenylenediamines mediated by NIS has been described so far. As an extension of our works toward developing procedures for N-heterocyclic systems, herein we report a mild, effective, and metal-free synthetic procedure for the production of quinoxaline derivatives through NIS-mediated coupling of o-phenylenediamines and sulfoxonium ylides.

2. Results and Discussion

In an examination of effective and trivial conditions for the manufacture of quinoxalines (3), we selected the reaction of o-phenylenediamine (1a) (1.0 mmol) and sulfoxonium ylide (2b) (1.0 mmol) as a model reaction to optimize the reaction conditions. We initiated testing our assumption, employing o-phenylenediamine and sulfoxonium ylide with 1.1 equiv of N-chlorosuccinimide (NCS) in CH3CN at room temperature for 5 h, as denoted in Table . A moderate yield of quinoxaline (3a) was detected in the presence of CH3CN, which established that the cyclization of o-phenylenediamine can be performed (Table , entry 1).

1. Optimization of Reaction Conditions .

2.

entry reagent (equiv) solvent time (h) yield
1 NCS (1.1) CH3CN 5 40
2 NCS (1.5) CH3CN 4 52
3 NBS (1.5) CH3CN 4 61
4 NBS (1.8) CH3CN 3 70
5 NIS (1.8) CH3CN 3 78
6 NIS (1.8) THF 3 68
7 NIS (1.8) EtOAc 2 82
8 NIS (1.8) CH 2 Cl 2 2 91
9 NIS (1.8) DCE 2 85
10 NIS (1.8) CH3NO2 3 60
11 NIS (1.8) acetone 10 30
12 NIS (1.8) 1,4-dioxane 10 25
13 NIS (1.8) DMF 24 trace
14 NIS (1.8) DMSO 24 trace
15 NIS (1.8) CCl4 24 trace
16 NIS (1.5) CH2Cl2 4 77
17 NIS (1.6) CH2Cl2 3 84
18 NIS (1.7) CH2Cl2 2 87
19   CH2Cl2 24 no reaction
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a

Reaction conditions: o-phenylenediamine (1.0 mmol), β-ketosulfoxonium ylide (1.0 mmol), and solvent (5 mL). The bold data signifies that the optimal result was attained with 1.8 equiv. of NIS in CH2Cl2 solvent within 2 h at room temperature.

b

Isolated yield.

c

In the absence of NIS.

Later on, we reviewed the other reaction parameters like N-haloimides and their equivalents and different types of solvents. A comprehensive report on the effect of N-haloimides such as N-chlorosuccinimide (NCS), N-bromosuccinimide (NBS), N-iodosuccinimide (NIS) and its loading, and various solvents is provided in Table . The optimal result was attained with 1.8 equiv of NIS in a CH2Cl2 solvent within 2 h at room temperature (Table , entry 8). Initially, we kept the same solvent and employed various N-haloimides. Enhancement of NCS loading to 1.5 equiv improved the product yield to 52% within 4 h (Table , entry 2). The optimal conditions were achieved using 1.8 equiv of NIS in CH2Cl2 at room temperature, affording the product in 2 h (Table , entry 8). Initially, the same solvent was maintained while screening various N-haloimides. Increasing the loading of NCS to 1.5 equiv improved the yield to 52% within 4 h (Table , entry 2). We then replaced NCS with NBS in the presence of CH3CN, and an enhancement in the product yield of 3b was observed (entry 3).

Further, the enhancement of NBS loading to 1.8 equiv additionally enhanced the product yield to 70% and also decreased the reaction time (entry 4). To enhance the product yield, we further replaced NBS with NIS in the presence of CH3CN, and an enhancement in the product yield was observed (entry 5). After achieving a good yield with NIS in CH3CN, we then tested various solvents for the reaction. Replacement of CH3CN with THF decreased the product yield to 68% (entry 6).

The utilization of EtOAc enhanced the product yield to 82% and also decreased the reaction time (entry 7). Replacement of EtOAc with CH2Cl2 generated the anticipated product in an excellent yield (91%) within 2 h (entry 8). However, a lower product yield was observed for DCE (entry 9). Further, the replacement of DCE with CH3NO2 generated a lower product yield (entry 10). A poor yield of the product was observed when we employed acetone for the reaction (entry 11). Later on, we employed polar aprotic solvents such as 1,4-dioxane, DMF, and DMSO in the presence of 1.8 equiv of NIS. A poor yield of the product was observed when we employed 1,4-dioxane as a solvent (entry 12). However, trace product yields were observed when we employed DMF and DMSO for the reaction (entries 13 and 14). Similarly, a trace product yield was observed in the presence of CCl4 as a solvent (entry 15). The reduction of NIS loading to 1.5 equiv significantly lowers the product yield to 77% and also increases the reaction time (Table , entry 16). The increment of NIS loading from 1.5 to 1.6 equiv enhanced the product yield (entry 17). Similarly, enhancement of NIS loading to 1.7 equiv further increased the product yield (entry 18). Furthermore, no further enhancement in the product yield was observed, when the equiv of NIS increased from 1.8 to 2.0 or 2.2 equiv in CH2Cl2. In the absence of NIS, no expected product was identified. The reaction did not progress even after 24 h of stirring, and o-phenylenediamines and sulfoxonium ylides remained unreacted (entry 19).

Afterward, with the optimal reaction conditions in hand, we turned our consideration to the scope of several o-phenylenediamines and sulfoxonium ylides as depicted in Scheme . A diverse range of sulfoxonium ylides was employed as the source of the reaction partner to synthesize the quinoxaline derivatives in excellent to good yields (91–63%) (Scheme , compounds 3a–3r).

2. Production of Quinoxalines (3a–3r)­ .

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a Reaction conditions: o-phenylenediamines (1.0 mmol), β-ketosulfoxonium ylides (1.0 mmol), NIS (1.8 mmol), and CH2Cl2 (5 mL).

The substrate scope revealed that an extensive range of o-phenylenediamines and sulfoxonium ylides were well tolerated during the reactions. Moreover, in all of the situations, the reactions proceeded efficiently to yield the corresponding desired products (3a–3r). The steric and electronic effects of several substituents at R1 of o-phenylenediamines and R2 of sulfoxonium ylides were tried under the optimal reaction conditions to address the factors that decide the product yields. Primarily, we keep 2-aminobenzaldehyde and discover the substrate scope of the sulfoxonium ylides. Additionally, numerous sulfoxonium ylides (2a–2o) were reacted with o-phenylenediamines under the optimized reaction conditions.

Remarkably, sulfoxonium ylides with both alkyl and aryl substituents reacted efficiently to produce the corresponding products 3a–3r in 63–91% yields. During the substrate scope, we observed that substrates with electron-donating groups generate higher yields compared to the substrates with electron-withdrawing groups. Sulfoxonium ylides with electron-donating groups such as −CH3 and –OCH3 on the aryl rings generate the desired products in excellent yields (Scheme , compounds 3b–3d). However, sulfoxonium ylides with electron-withdrawing groups such as –F, –Br, and –NO2 on the aryl rings generated the desired products in good yields (compounds 3e–3h). Sulfoxonium ylides containing biphenyl and naphthalene rings were successfully converted to the corresponding quinoxaline derivatives with good yields of 80 and 73%, respectively (Scheme , compounds 3i and 3j). Moreover, sulfoxonium ylides featuring furan and thiophene rings were also employed for the reactions with o-phenylenediamine, producing the expected quinoxaline derivatives with good yields of 85 and 77%, respectively (Scheme , compounds 3k and 3l). Under the optimized reaction conditions, we were also able to couple sulfoxonium ylides with different aliphatic groups. Moreover, sulfoxonium ylides having aliphatic groups such as tert-butyl, cyclopropyl, and cyclohexyl were effectively converted to the desired products in good yields (Scheme , compounds 3m–3o). Afterward, under the optimal conditions, we also performed the reaction between substituted o-phenylenediamine 1b, 1c, and 1d with sulfoxonium ylide 2a, resulting in a good yield of the desired products (compound 3p–3r).

Heterocyclic o-phenylenediamine such as pyridine-2,3-diamine reacts with sulfoxonium ylide, producing the corresponding phenylpyrido-pyrazine derivative in an 87% yield (compound 3p). Similarly, disubstituted o-phenylenediamine such as 4,5-dimethylbenzene-1,2-diamine reacts with sulfoxonium ylide, generating 6,7-dimethyl-2-phenylquinoxaline in a 74% yield (compound 3q). Later, under the optimal conditions, we also coupled monosubstituted o-phenylenediamine, such as 4-methoxybenzene-1,2-diamine, with sulfoxonium ylide 2a, resulting in the formation of 3r and 3r’ with an 85% yield. This reaction produced a 1.3:1 mixture of regioisomers for monosubstituted diamine. Monosubstituted diamine produced regioisomers because diamine has two different −NH2 groups with respect to the substituent present in the benzene ring. Monosubstituted diamine gives two different regioisomers under the optimized reaction conditions, displaying the limitations of this protocol.

After the successful utilization of this protocol for o-phenylenediamines, we have also applied this approach for the synthesis of trisubstituted pyrazine derivatives through the reactions between 2,3-diaminomaleonitrile and sulfoxonium ylides under the same optimal reaction conditions as depicted in Scheme .

3. Synthesis of Trisubstituted Pyrazines (5a–5d)­ .

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a Reaction conditions: 2,3-diaminomaleonitrile (1.2 mmol), β-ketosulfoxonium ylides (1.0 mmol), NIS (1.8 equiv), and CH2Cl2 (5 mL).

A diverse range of sulfoxonium ylides were employed to synthesize trisubstituted pyrazine derivatives from good to excellent yields (67–89%) (Scheme , compounds 5a–5d). A good yield of trisubstituted pyrazine was observed for sulfoxonium ylides containing an aliphatic group such as tert-butyl (Scheme , compound 5a). Sulfoxonium ylides having aromatic groups such as –Ph and −4-OCH3-Ph equally react with 2,3-diaminomaleonitrile to produce the corresponding trisubstituted pyrazines in excellent yields (compounds 5b and 5c). Similarly, heterocyclic sulfoxonium ylide 2k reacts with 2,3-diaminomaleonitrile, manufacturing the corresponding product in an 80% yield (compound 5d).

2.1. Gram-Scale Synthesis

To authenticate the applied application and to categorize the synthetic efficacy of this established procedure, later, we implemented a gram-scale reaction of o-phenylenediamine 1a (8.0 mmol, 0.864 g) with sulfoxonium ylide 2d (8.0 mmol, 1.808 g) and of 2,3-diaminomaleonitrile 4 (8.4 mmol, 0.907 g) with sulfoxonium ylide 2a (7.0 mmol, 1.372 g) (Scheme ). The desired products 3d (1.388 g, 84%) and 5b (1.110 g, 77%) were observed to be similar to those of small-scale reactions (Schemes and , compounds 3d (90%), 5b (84%)). This significance stated that the reported protocol could be implemented for large-scale manufacture.

4. Gram-Scale Synthesis of Compounds 3d and 5b .

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Based on a literature survey and sulfoxonium ylide reactivity, − a probable reaction mechanism for the construction of quinoxalines has been anticipated and shown in Figure . The iodine center of N-iodosuccinimide is electrophilic in nature. Initially, N-iodosuccinimide reacts with the α-carbon of β-ketosulfoxonium ylide 2a to generate the intermediate A. Nucleophilic attack of o-phenylenediamine on the intermediate A affords the intermediate B, which subsequently eliminates HI to generate the imine intermediate C. Finally, the –NH2 group of the intermediate C undergoes an intramolecular nucleophilic attack on the carbonyl carbon to produce the cyclic intermediate D with the subsequent removal of H2O, finally affording the desired product.

2.

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A probable mechanism for the synthesis of quinoxalines.

3. Experimental Section

3.1. General Methods

Chemicals were purchased from commercial sources and used without further purification. All reactions were monitored by TLC using precoated silica gel aluminum plates. Visualization of the TLC plates was accomplished with an UV lamp. Column chromatography was performed using silica gel (60–120 mesh size) with EtOAc-hexane as an eluent. All products were characterized by NMR, IR, and HRMS spectral data. 1H and 13C NMR spectra were recorded in deuterated chloroform (CDCl3) on 500/600 MHz and 126/151 MHz spectrometers, respectively. Chemical shifts were reported in parts per million (ppm, δ) downfield from tetramethyl silane. Proton coupling patterns are described as singlet (s), doublet (d), triplet (t), quartet (q), multiplet (m), and broad (br).

3.2. General Procedure for the Synthesis of Sulfoxonium Ylides

3.2.Sulfoxonium ylides were prepared according to the reported procedure. To a stirred solution of potassium tert-butoxide (28 mmol, 4 equiv) in THF (30 mL), trimethylsulfoxonium iodide (21 mmol, 3 equiv) was added at room temperature. The resulting mixture was refluxed for 2 h. Then, the reaction mixture was cooled to 0 °C. Acyl chloride (7 mmol) in THF (5 mL) was added to the reaction mixture. After that, the reaction was warmed to room temperature and stirred for an extra 3 h. After TLC monitoring, the solvent was removed under pressure, and water (20 mL) and DCM (30 mL) were added to the resultant slurry. The organic layer was separated, and the aqueous layer was washed with DCM (2 × 30 mL). The combined organic layer was dried over anhydrous Na2SO4, filtered, and evaporated to dryness. The crude product was purified by a mixture of EtOAc/diethyl ether with constant stirring, resulting in the precipitation of a pure ylide. These ylides were filtered through a Buchner funnel under vacuum and washed with cold EtOAc/diethyl ether to afford the corresponding sulfoxonium ylides as solid compounds.

3.3. General Procedure for the Synthesis of Quinoxalines (3a–3r)

A mixture of β-ketosulfoxonium ylides (1.0 mmol), o-phenylenediamines (1.0 mmol), and NIS (1.8 mmol) in CH2Cl2 (5 mL) was stirred at room temperature for 2 h. After TLC monitoring, the solvent was removed under pressure. Water (10 mL) was added to the reaction mixture, and it was extracted with ethyl acetate (3 × 10 mL). The combined organic layer was dried over anhydrous Na2SO4 and the solvent was concentrated under vacuum. The residue was purified by silica gel column chromatography (5–10% EtOAc in hexane) to afford the corresponding pure products.

4. Conclusions

We have discovered and established an efficient, facile, mild, and metal-free N-iodosuccinimide-mediated approach for the synthesis of quinoxalines from o-phenylenediamines and sulfoxonium ylides at room temperature. Sulfoxonium ylides and o-phenylenediamines decorated with several functional groups were well tolerated during the reactions and produced the desired products in good to excellent yields through a simple and trivial procedure. We also executed gram-scale reactions to validate the practicality of this method. Metal-free, operational simplicity, mild reaction conditions, atom economy, and high yields are some new and innovative aspects/significant features of this protocol. This invention of a mild and green methodology for NIS-mediated synthesis of quinoxalines can be implemented in a wide range of products and services across several key industries such as pharmaceutical industries, chemical industries, biotechnology, materials science, agriculture, etc. In drug discovery and development, our methodology can accelerate the synthesis of novel drug candidates, leading to more efficient and cost-effective drug development processes.

Supplementary Material

ao5c09337_si_001.pdf (1.9MB, pdf)

Acknowledgments

The authors extend their appreciation to the Deanship of Research and Graduate Studies at University of Tabuk for funding this work through Research No. S-1444-0078.

The characterization data of this study is available in the Supporting Information.

The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acsomega.5c09337.

  • Data and general methods; general procedure for the synthesis of sulfoxonium ylides; general procedure and characterization data of compounds 3a–3r; general procedure and characterization data of compounds 5a–5d; and 1H and 13C NMR spectra for the prepared compounds. (PDF)

H.P., S.M., M.Y.W., and M.O.A.: conceptualization; H.P., S.M., M.Y.W., M.O.A., and S.K.: methodology; S.M. and S.K.: software; M.O.A. and S.K.: validation; H.P., S.M., M.Y.W., and S.K.: formal analysis; H.P., S.M., M.Y.W., and M.A.: investigation; H.P., S.M., S.K., M.Y.W., and M.O.A.: resources; M.O.A. and S.K.: data curation; H.P., S.M., S.K., M.Y.W., and M.O.A.: writingoriginal draft preparation; H.P., M.Y.W., and S.M.: writingreview and editing; M.O.A. and S.K.: visualization; H.P., S.M., and S.K.: supervision; H.P., S.M. M.O.A., and M.Y.W.: project administration; and H.P.: funding acquisition. All authors have read and agreed to the published version of the manuscript.

This innovative methodology described herein has been filed for patent protection (U.S. Patent application number 19/033,327).

The authors declare no competing financial interest.

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Associated Data

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Supplementary Materials

ao5c09337_si_001.pdf (1.9MB, pdf)

Data Availability Statement

The characterization data of this study is available in the Supporting Information.

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