Abstract
First, a Brønsted acid ionic liquid (BAIL) in the role of a double acid-base called 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT) was produced, and its skeleton was determined via TGA, mass, 13C NMR, 19F NMR, 1H NMR and FT-IR data. Further, it was successfully applied in the preparation of dibenzo-chromeno-phenazine-dione derivatives (1a-12a, 9–15 min, 90–98%) via one-pot multicomponent domino reaction among 2 mmol 2-hydroxynaphthalene-1,4-dione, 1 mmol benzene-1,2-diamine, and 1 mmol aldehydes under optimal conditions (5 mol% of PBPBSDT, solvent-free, 60 °C). The proper reproducibility of the PBPBSDT homogeneous catalyst (5 times), solvent-free medium, reasonable TON (Turnover Number) and TOF (Turnover Frequency) numbers, the non-metallic framework of the catalyst, and the formation of C-N, C = N, C-C, C = C, C-O bonds in a single operation are the distinct advantages of this protocol.
Keywords: Dibenzo-chromeno-phenazine-diones. Multicomponent domino reactions (MCDRs). 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT). Solvent-free medium
Subject terms: Catalysis, Medicinal chemistry, Organic chemistry
Introduction
Ionic liquids (ILs) are weakly coordinated ionic compounds (organic salts) that lead to the liquefaction of these materials below 100 °C or even at ambient temperature1,2. Using ILs in organic transformations as eco-friendly catalysts is deemed an advanced technology due to their outstanding properties such as easy recyclability, low vapor pressure, functional variability, non-flammability, acidity/basicity of cations/anions, less corrosion compared to mineral bases and acids, high thermal and chemical durability, tunable solubility, and capability to catalyze various synthetic pathways3–6. Brønsted acidic ionic liquids (BAILs) are an important subgroup of these liquids, which are widely used as efficient catalysts in organic synthesis due to their advantages of traditional liquid and solid acids, mild acidic nature, easy design and production, and good efficacy and selectivity6,7. Recently, some species of this subset whose cationic part contains SO3H bonded to positive nitrogen and their anionic part comprises basic sites (although weak like AlCl4ˉ) as a bi-functional catalyst (or dual acid-base) in various synthetic transformations have been reported in the literature8–10. Therefore, the synthesis of such ILs can be crucial in aiding reactions that simultaneously require acidic and basic sites to be catalyzed11.
Today, the development of simple, cost-effective, and green chemistry-friendly organic transformations has been of great significance in terms of environmental sustainability12,13. A fundamental step in this direction is using one-pot multicomponent domino reactions (MCDRs) under solvent-free conditions14. These reactions have provided the most efficient platform for the synthesis of complex compound libraries in the screening of active pharmaceutical and biological candidates15–18. MCDRs, at the same time as operating simplicity and improving atomic economy, can prevent costly and time-consuming procedures for the purification of diverse precursors; so they are a constant challenge in the front line of organic synthesis, especially in the generation of heterocyclic compounds15–19.
In the pharmaceutical industry, heterocyclic systems with chromene and phenazine segments (e.g., dibenzo-chromeno-phenazine-diones) are important because they are the vital framework of many drugs and biologically active substances20–22. Various biological properties of chromen core have been proven, including antimicrobial, antitumor, antifungal, antiasthmatic, antioxidant, and anti-HIV activities23–28. Also, phenazine systems present in natural and synthetic products exhibit various biological functions including antimicrobial, antibiotic, antiparasitic, antimalarial and antitumor activities in solid and leukemia tumors29–33. For example, pyridazinophenazinedione derivatives and pyridophenazinediones are well known for their anticancer properties31,32. However, notwithstanding their established biological applications, only very few protocols describing their production have been reported in the literature34–38. Therefore, it is very important to introduce new methods that allow the rapid and easy production of these valuable compounds while minimizing the disadvantages of previous methods.
Taking into account the above, by gathering the advantages of domino reactions, multicomponent reactions, bi-functional catalysts, solvent-free environment, and recyclable ILs, we presented a simple and effective protocol at a mild temperature of 60 °C for the synthesis of dibenzo-chromeno-phenazine-dione derivatives using PBPBSDT ionic liquid via one-pot MCDR of 2 mmol 2-hydroxynaphthalene-1,4-dione, 1 mmol benzene-1,2-diamine, and 1 mmol aldehydes. Notably, according to our investigations, this is the first report of the production of dibenzochromeno-phenazine-dione derivatives with an ionic liquid catalyst.
Experimental
Materials and apparatus
The description of the specifications of all starting materials and apparatus is given in the related files.
Procedure for the preparation of ionic liquid PBPBSDT
At the beginning, 4 mmol of 1,3-di(pyridin-4-yl)propane (dissolved in 25 mL dichloromethane) was gradually added to 8 mmol of chlorosulfuric acid (dissolved in 25 mL dichloromethane) within 5 min at 10 °C. Next, the resulting solution was permitted to heat to 25 °C, and it stirred at this temperature for 120 min. The dichloromethane was evaporated, and the resulting was cleaned with petroleum ether (3 × 4 mL), and it dried under vacuum at 70 °C to provide Intermediate I. At the last stage, 8 mmol of trifluoroacetic acid (TFA) was gradually added to 4 mmol of intermediate I. The resulting solution was stirred for 5 min at 25 °C, and then 60 min at 60 °C to synthesize PBPBSDT (a viscous yellow oil in 98% yield) (Fig. 1).
Fig. 1.
The preparation of PBPBSDT.
General procedure for producing dibenzo-chromeno-phenazine-diones
In the first step under a domino reaction at 60 °C, a mixture of 5 mol% PBPBSDT, 1 mmol benzene-1,2-diamine, and 1 mmol 2-hydroxynaphthalene-1,4-dione was stirred in solvent-free conditions (5 min) to give Intermediate II (Fig. 2). Subsequently, during a multicomponent reaction, 1 mmol 2-hydroxynaphthalene-1,4-dione, and 1 mmol aldehyde were added to the Intermediate II. This mixture was stirred with TLC monitoring until the end of the reaction. After completely consuming the starting material, the residue was cooled to ambient temperature, and PBPBSDT was isolated (based on the recycle section technique). Eventually, the pure dibenzo-chromeno-phenazine-diones were achieved via recrystallization of the residue in 95% ethanol.
Fig. 2.
General procedure for producing dibenzo-chromeno-phenazine-diones.
Results and discussion
Studies to confirm the structure of 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT)
In this section, the structure of PBPBSDT was evaluated using Fourier transform infrared spectroscopy (FT-IR), fluorine (19F), carbon (13C), proton (1H) NMR, thermal analysis (TGA), and mass spectrometry.
In Fig. 3, the FT-IR pattern of PBPBSDT is displayed, and the findings are compiled in Table 1. As can be observed in Table 1; Fig. 3, the wavenumbers corresponding to anticipated bonds and functional groups have appeared in the PBPBSDT spectrum. The literature supports our results10,40–42.
Fig. 3.
The FT-IR spectrum of PBPBS DT.
Table 1.
The FT-IR data of PBPBSDT.
| Wavenumber (cm− 1) | Related functional group or bond |
|---|---|
| 2500–3500 | O–H stretching vibration of SO3H |
| 3132 | C–H symmetric stretching = |
| 3016 | C–H symmetric stretching |
| 1702 | C = O stretching |
| 1618 | C = N stretching |
| 1535, 1495 | C = C stretching |
| 1433 | CH2 bending |
| 1308 | C–O stretching |
| 1224 | C–F stretching |
| 1191 and 1132 | S–O asymmetric and symmetric stretching |
| 1036 | S–OH bending |
| 889 | N–S stretching |
| 791 | C–H out-of-plane = |
| 550 | S–O bending |
The mass spectrum of 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate revealed the molecular mass (M+), (M++1), and (M++2) at m/z 588, 589 and 590, respectively (Fig. 4).
Fig. 4.
Part of the PBPBSDT mass spectrum pattern.
In the scope of 50–500 °C, the PBPBSDT thermal behavior was investigated by analyzing its TGA diagram (Fig. 5a). The results indicated that the weight loss of ionic liquid occurs in the following three temperature ranges: 50 to ~ 150 (− 17.41%), 150 to 322 °C (− 55.33%), and 322 to 500 °C (− 27.26%). Based on similar literature, the weight loss in the first stage can be attributed to the evaporation of the absorbed solvents in PBPBSDT, and in the second and third stages to the decomposition of its organic framework8. Therefore, according to the onset temperature of PBPBSDT weight loss (i.e., from 150 °C onwards), it can be said that this ionic liquid has enough stability to catalyze an MCDR at a mild temperature of 60 °C. In another study, the thermal stability of intermediate I (Fig. 5b), was compared with PBPBSDT under the same conditions. The results showed that the thermal behavior of these two ionic liquids is similar, but decomposition onset temperature of intermediate I is slightly higher (50 °C). This is due to the thermal stability of chloride anion (Clˉ) compared to trifluoroacetate (CF3COOˉ). These results are consistent with previously observed trends in ionic liquids43.
Fig. 5.
TGA diagrams of PBPBSDT (a), and intermediate I (b).
The proton (1H), carbon (13C), and fluorine (19F) NMR spectra of PBPBSDT are shown in Figs. 6, 7 and 8, correspondingly. The data of these three spectra well defines the generation of PBPBSDT as follows: 1H NMR (500 MHz, DMSO-d6) δ (ppm): 9.96 (br., 2 H, OH), 9.11 (d, J = 8.1 Hz, 4 H, HAr), 8.40 (d, J = 8.1 Hz, 4 H, HAr), 2.59 (t, J = 9.9 Hz, 4 H, 2CH2), 1.94 (quintet, J = 9.9 Hz, 2 H, CH2) (Fig. 6); 13C NMR (125 MHz, DMSO-d6) δ (ppm): 159.07–158.11 (q, 2JC−F = 40.2 Hz), 143.55, 141.97, 129.36, 124.95–118.06 (q, 1JC−F = 287.1 Hz), 35.92, 29.07 (Fig. 7); 19F NMR (235 MHz, DMSO-d6) δ (ppm): -70.59 ppm (Fig. 8).
Fig. 6.
1H NMR spectrum of PBPBSDT.
Fig. 7.
13C NMR spectrum of PBPBSDT.
Fig. 8.
19F NMR spectrum of PBPBSDT.
Catalytic experiments
Producing dibenzo-chromeno-phenazine-diones catalyzed using PBPBSDT
In this section, how to optimize the protocol for creating C-N, C = N, C-C, C = C, C-O bonds during the production of dibenzo-chromeno-phenazine-dione derivatives under solvent-free conditions in a single operation via one-pot multicomponent domino reaction was monitored. In this regard, the reaction between 1 mmol benzene-1,2-diamine, 2 mmol 2-hydroxynaphthalene-1,4-dione, and 1 mmol 3-nitrobenzaldehyde was considered as a benchmark reaction to implement this idea. We first studied the progress of the model reaction in the presence of 5 mol% of each component of the PBPBSDT skeleton, and 1,3-n-propyl-bipyridinium bisulfonic acid-dichloride (Intermediate I), at a temperature of 80 ºC (Table 2, entries 1–4). The results showed that none of them alone can be a suitable catalyst for improving the reaction conditions (Time: 20 min, Yield: 25–67%). At 100 °C, no product was produced even after 60 min without PBPBSDT (Table 2, entry 5). Then, we investigated the reaction in the presence of 3 to 8 mol% of ionic liquid at a temperature of 40 to 70 °C (Table 3, entries 6–10). Table 2 showed, the best temperature for this synthetic conversion is 60 °C (Table 2, entry 6). It should be noted that by increasing the temperature to 70 °C, no significant difference in product yield was seen (Table 2, entry 9), but decreasing it to 40 °C caused the yield to drop to 73% (Table 2, entry 7). Accuracy in the results of entries 6, 8, and 10 indicated that 5 mol% PBPBSDT was sufficient to quickly carry out the reaction (Table 2, entry 6). Therefore, the conditions mentioned in entry 6 was considered as the optimal conditions. It is noteworthy that the attempt with PTSA and K2CO3 as a catalyst under optimal conditions was not successful; so that the corresponding products were obtained in 20 min with a yield of 48% and trace (Table 2, entries 11 and 12).
Table 2.
Screening of reaction conditions for preparing 5a in the absence of solvent.
| Entry | Catalyst | Temp. (°C) |
Catalyst amount (mol%) |
Time (min) |
Yielda (%) |
|---|---|---|---|---|---|
| 1 | 1,3-di(pyridin-4-yl)propane | 80 | 5 | 20 | 25 |
| 2 | Chlorosulfonic acid | 80 | 5 | 20 | 29 |
| 3 | Trifluoroacetic acid (TFA) | 80 | 5 | 20 | 33 |
| 4 | Intermediate I | 80 | 5 | 20 | 67 |
| 5 | – | 100 | – | 60 | NRb |
| 6 | PBPBSDT | 60 | 5 | 10 | 97 |
| 7 | PBPBSDT | 40 | 5 | 10 | 73 |
| 8 | PBPBSDT | 60 | 8 | 10 | 98 |
| 9 | PBPBSDT | 70 | 5 | 10 | 98 |
| 10 | PBPBSDT | 60 | 3 | 10 | 70 |
| 11 | PTSA (as an acid)c | 60 | 5 | 20 | 48 |
| 12 | K2CO3 (as a base) | 60 | 5 | 20 | Trace |
aIsolated yield.
b No reaction.
cp-Toluenesulfonic acid.
Table 3.
Synthesizing dibenzo-chromeno-phenazine-diones catalyzed via PBPBSDT.
| ||||||
|---|---|---|---|---|---|---|
| Product | Ar | Time (min) | Yield (%)a | TON |
TOF (min− 1) |
M.p. (ºC) Found (Reported) |
| 1a | 4-O2N-C6H4 | 9 | 98 | 19.60 | 2.17 | 273–275 (274–275) 35 |
| 2a | 3-O2N-C6H4 | 10 | 98 | 19.60 | 1.96 | 369–371 (368–370) 36 |
| 3a | 2-O2N-C6H4 | 10 | 97 | 19.40 | 1.94 | 292–294 (293–295) 37 |
| 4a | 3-CN-C6H4 | 10 | 97 | 19.40 | 1.94 | 287–289 (286–288) 38 |
| 5a | 4-Cl-C6H4 | 10 | 98 | 19.60 | 1.96 | 324–326 (324–326) 36 |
| 6a | 2-Cl-C6H4 | 12 | 94 | 18.80 | 1.56 | 334–336 (336–338) 36 |
| 7a | 2,4-Cl2-C6H3 | 13 | 92 | 18.40 | 1.41 | 329–331 (330–332) 36 |
| 8a | 4-Me-C6H4 | 12 | 93 | 18.60 | 1.55 | 333–335 (332–334) 35 |
| 9a | 4-MeO-C6H4 | 13 | 94 | 18.80 | 1.44 | 339–341 (341–342) 36 |
| 10a | 3,4-(MeO)2-C6H3 | 15 | 90 | 18.00 | 1.20 | 319–322 (320–321) 38 |
| 11a | 4-OH-C6H4 | 13 | 91 | 18.20 | 1.40 | 299–301 (301–303) 38 |
| 12a | 2-OH-5-NO2-C6H4 | 15 | 90 | 18.00 | 1.20 | 364–366 (365) 38 |
aIsolated yield.
Next, the versatility and activity scope of PBPBSDT as a bi-functional ionic liquid catalyst was evaluated by reacting different aromatic aldehydes under optimal conditions (Table 3). All reactions were completed in 9 to 15 min and led to the formation of target molecules (Time: 9–15 min, Yield: 90–98%) in high yield. Therefore, it was confirmed that PBPBSDT is a suitable catalyst for this synthetic transformation and our idea for its design was reasonable.
PBPBSDT ionic liquid is a bi-functional catalyst due to having both acidic (–SO3H) and basic (CF3COOˉ) positions8,11. In Fig. 9, an interesting mechanism is shown with the help of its acidic and basic sites to produce dibenzo-chromeno-phenazine-diones. Previous literature supports the dual functionality of PBPBSDT35,36,44,45. The reaction mechanism includes 9 stages, and the ionic liquid helps to carry out the following processes: expediting the tautomerization reaction (step 1), activation of the nucleophiles (steps 2, 5, 7 and 8), activation of the electrophiles (steps 1, 4, 7 and 8), facilitating water elimination (steps 3, 6 and 9), and accelerating the cyclization step (step 8).
Fig. 9.
A proposed mechanism in the preparing dibenzo-chromeno-phenazine-diones.
Catalyst recyclability
The reproducibility (i.e., recyclability and reusability) of catalysts, especially their homogeneous types, is an essential advantage for commercial and industrial applications. Accordingly, after the completion of the reaction, the remainder was extracted by adding 20 mL of hot ethyl acetate to isolate PBPBSDT (because the catalyst, unlike the product, is insoluble in this solvent). The removed catalyst was triturated with a one-to-one mixture of ethanol and ethyl acetate and dried at 60 °C for next use. In Fig. 10, the results of five times PBPBSDT recycling during the production of derivative 2a are displayed as a function of time and product percentage. The slight decline in the performance of our ionic liquid is due to its loss of 3–5% during the recovery process.
Fig. 10.
The results of five times of PBPBSDT recycling during the production of derivative 2a.
Comparison
To appraise the current protocol against other reported approaches in the producing dibenzo-chromeno-phenazine-dione derivatives, the catalytic ability of the PBPBSDT was compared with some catalysts published in the literature, with the criterion of placing factors such as the reaction medium with or without solvent, reaction time, amount of catalyst used, and product yield. For doing this, the reaction of preparing product 2a was considered as a model and the results were tabulated in Table 4. As the table shows, PBPBSDT is superior to the reported catalysts in most parameters mentioned. In addition, this ionic liquid catalyst is comparable in terms of low toxicity, easy isolation, and availability and low price of its parents.
Table 4.
Evaluation of the catalytic performance of PBPBSDT with other available catalysts in the producing dibenzo-chromeno-phenazine-diones.
| Catalyst | Conditions | Time (min) | Yielda (%) | Ref. |
|---|---|---|---|---|
| PBPBSDT (5 mol%) | Solvent-free, 60 ºC | 10 | 98 | – |
| Zr-guanine-MCM-41 (0.30 mol%) | PEG-400, 100 ºC | 120 | 90 | 35 |
| para-Toluenesulfonic acid (20 mol%) | PEG-400, 80 ºC | 120 | 91 | 36 |
| Ni-Gly-isatin@boehmite (0.04 g) | PEG-400, 80 ºC | 300 | 90 | 37 |
| γ-Fe2O3@SiO2‐SCH2CO2H (0.03 g) | EtOH/H2O (1:1), 70 ºC | 120 | 94 | 38 |
| L-proline (20 mol%) | H2O, Microwave, 180 W, max. 70 °C | 10 | 95 | 39 |
aIsolated yield.
Conclusions
Concisely, we have presented 1,3-n-propyl-bipyridinium bisulfonic acid-ditrifluoroacetate (PBPBSDT), as a highly capable, homogeneous, and bi-functional ionic liquid in the preparing dibenzo-chromeno-phenazine-dione derivatives through the one-pot MCDR of 1 equivalent aryl aldehydes, 2 equivalents 2-hydroxynaphthalene-1,4-dione, and 1 equivalent benzene-1,2-diamine under the facile condition with high yields in short reaction times (solvent-free, 60 °C, 90–98%, 9–15 min). Then, in justifying its influential role as an acid and base duel in promoting the reaction, a suitable mechanism was demonstrated with the help of its acidic and basic position (i.e., –SO3H and CF3COOˉ). Appropriate reproducibility of the catalyst despite its homogeneous nature (5 times), operational simplicity, solvent-free conditions, and easy work-up are the other benefits of this methodology.
Acknowledgements
The authors are grateful to acknowledge the Manipur International University, Imphal, India.
Author contributions
Chou-Yi Hsu: synthesized dibenzo-chromeno-phenazine-dione 1a to 6a and edited the manuscript.Riyadh Abdulkareem: synthesized dibenzo-chromeno-phenazine-dione 7a to 12a.Harikumar Pallathadka: synthesized the ionic liquid.Vikrant Abbot: optimized reaction circumstances for the production of dibenzo-chromeno-phenazine-diones.Mamata Chahar: characterized the structure of derivatives 1a and 5a with 1 H NMR and 13CNMR.Dilsora Abduvalieva: characterized the structure of derivatives 9a and 12a with 1 H NMR and 13CNMR.Yasser Fakri Mustafa: characterized the structure of the ionic liquid by 13 C NMR, 19 F NMR, and 1 H NMR techniques.Usama S. Altimari: characterized the structure of the ionic liquid by TGA, mass, and FT-IR techniques. Abeer mhussan jabbar: wrote the manuscript. Ahmed Hussein Zwamel: edited the manuscript and designed the Schemes.
Data availability
The data that support the findings of this study are available on request from the corresponding author.
Declarations
Ethics approval and consent to participate
The author’s declare that the paper is not be submitted simultaneously to another journal. The submitted work is original and has not been published elsewhere in any form or language, and the authors have no conflict of interest regarding this manuscript. The authors agree to participate in submitting our manuscript to this journal, and agree to the publication of our research data in this journal.
Consent for publication
We have confirmed.
Competing interests
The authors declare no competing interests.
Footnotes
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Contributor Information
Riyadh Abdulkareem, Email: riyad.abdulkarim@uoanbar.edu.iq.
Harikumar Pallathadka, Email: harikumar@miu.edu.in, Email: pallathadkaharikumar1@gmail.com.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Data Availability Statement
The data that support the findings of this study are available on request from the corresponding author.