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Communication

Ultrasound Assisted One-Pot Synthesis of Novel 3-(Aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines in Water

by
Ayoub El Mahmoudi
1,
Khalid Karrouchi
2,
Hamza Tachallait
3 and
Khalid Bougrin
1,3,*
1
Equipe de Chimie des Plantes et de Synthèse Organique et Bioorganique, URAC23, Faculty of Science, B.P. 1014, Geophysics, Natural Patrimony and Green Chemistry (GEOPAC) Research Center, Mohammed V University in Rabat, Rabat 10010, Morocco
2
Laboratory of Analytical Chemistry and Bromatology, Faculty of Medicine and Pharmacy, Mohammed V University in Rabat, Rabat 10010, Morocco
3
Chemical & Biochemical Sciences Green-Process Engineering (CBS), Mohammed VI Polytechnic University, Lot 660, Hay Moulay Rachid, Benguerir 43150, Morocco
*
Author to whom correspondence should be addressed.
Molbank 2022, 2022(4), M1529; https://doi.org/10.3390/M1529
Submission received: 18 November 2022 / Revised: 8 December 2022 / Accepted: 15 December 2022 / Published: 17 December 2022
(This article belongs to the Topic Heterocyclic Carbene Catalysis)
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Abstract

:
In this work, we present an efficient one-pot method for the synthesis of three new azo-isoxazoline derivatives (4a–c) from aromatic aldehydes, hydroxylamine hydrochloride and 4-(allyloxy)azobenzene. Thus, the azo-isoxazoline derivatives (4a–c) were synthesized via 1,3-dipolar cycloaddition using sodium dichloroisocyanurate (SDIC) as an eco-friendly and inexpensive oxidizing agent under ultrasound cavitation in water as a green solvent. The desired compounds 4a–c were obtained in high to excellent yields of 75–90%.

1. Introduction

Azo dyes belong to the most important class of chromophores, which are characterized by nitrogen–nitrogen double bonds «N=N», and have a wide range of applications in industry and pharmaceutical sectors [1,2]. In addition, azo dyes containing heterocycles have a wide spectrum of biological activities, which is mostly influenced by the nature of the heterocycle and position of the substituents, such as antibacterial, antifungal, antiviral, antitubercular, anticancer, anticonvulsant, antidiabetic, analgesic and anti-inflammatory, and chemosensing activities [3,4], hence the interest to synthesize more heterocycles with azo dyes.
On the other hand, isoxazolines are an important class of heterocyclic compounds that contain nitrogen and oxygen heteroatoms, which are very important in medicinal chemistry due to their various pharmacological properties, including anti-diabetic [5], anti-cancer [6], anti-inflammatory [7], antimicrobial [8], anti-stress [9], anti-Alzheimer [10], analgesic [11] and insecticidal properties [12].
Several approaches and methods for the synthesis of isoxazoline rings have been reported in the literature [13,14,15,16,17,18]. However, most 1,3-dipolar cycloadditions of alkenes with nitrile oxides are produced by the oxidation of aldoximes in organic solvents under conventional conditions, including metal-catalyzed processes [14,15,16,17,18]. Numerous oxidants, including Ni(ClO4)2 6H2O and NiBF4 6H2O as Lewis acid catalysts [14], Ru(acetone)(R,R)-(BIPHOP-F)Cp][SbF6] [15], organo-hypervalent iodine reagents [16], CrO2 and MnO2 [17], have been used to generate nitrile oxides from aldoximes. Other examples of the use of rare earth elements as catalysts in 1,3-dipolar cycloaddition reactions of nitrile oxide have also been described [18].
However, in the context of the current green chemistry trend, the use of alternative, non-toxic and renewable reaction media is attractive, such as water [19,20] and ionic liquids (ILs) [21], as well as alternative activation conditions, such as microwave (MW) [22,23] and ultrasound (US) activation [24,25].
As a part of our research into the use of selective, environmentally friendly and efficient catalysts combined with ultrasound as an alternative source of energy for the synthesis of bioactive aza-heterocycles [22,25,26,27,28,29,30], herein, we report a one-pot three-component approach for the synthesis of novel azo-isoxazolines (4a–c) from aromatic aldehydes 1a–c, hydroxylamine hydrochloride 2, and 4-(allyloxy)azobenzene 3, catalyzed by SDIC (or NaDCC) in water under ultrasound cavitation at room temperature (Scheme 1).

2. Results and Discussion

Recently, we reported a simple and environmentally friendly method for the synthesis of 3,5-disubstituted isoxazoles under ultrasonic cavitation using SDIC as an eco-friendly and inexpensive oxidant in water [25]. It is important to extend the application of this method to the synthesis of other heterocycles. First, our investigations were initiated with the condensation of aromatic aldehydes 1a–c with hydroxylamine, easily generated from hydroxylamine hydrochloride 2 under basic conditions, to provide the appropriate nitrile oxide in situ by oxidation of aromatic aldoximes by SDIC in water under ultrasonic cavitation. Thus, the nitrile oxide was trapped by 4-(allyloxy)azobenzene 3 as a dipolarophile via 1,3-dipolar cycloaddition, to give novel azo-isoxazolines 4a–c. The reaction was completed in 25–30 min via ultrasound cavitation, as attested by TLC monitoring, in good to excellent yields of 75–90% (Scheme 1).
In order to examinate the scope and limitations of this ultrasound-assisted reaction, we evaluated the reactivity of three aldehydes 1a–c. In general, we observed that both electron-poor and electron-rich aldehydes can be used in this reaction, leading to azo-isoxazolines isolated as pure products in good to excellent yields (75–90%), and high regioselectivity.
The azo-isoxazolines (4a–c) were fully characterized by 1H, 13C NMR, and LCMS spectra (See Supplementary Materials). For example, the 1H NMR spectrum of 5-((4-(phenyldiazenyl)phenoxy)methyl)-3-(p-tolyl)-isoxazoline 4a showed a multiplet at δ = 5.22–5.11 ppm due to the H-isoxazolinic proton, and two doublets of doublets at δ = 3.42 and 3.57 ppm for C4HaHb isoxazolinic protons. The N–CH2 protons appear as two doublets of doublets at δ = 4.18 and 4.28 ppm. This compound also showed a singlet, on average at δ = 2.42 ppm, which identifies the methyl group; thus, the presence of the signals at δ = 7.06–7.99 ppm is attributable to the different aromatic protons. The 13C NMR spectrum of 4a exhibited characteristic signals at δ = 21.5 ppm (CH3), 37.8 ppm (CH2-isoxazoline), 68.9 ppm (N-CH2), 78.4 ppm (CH-isoxazoline), 156.40 ppm (C=N-isoxazoline), and 160.97 ppm, 152.51 ppm, 147.2 ppm, 140.6 ppm, 130.6 ppm, 129.5 (2C) ppm, 129.1 (2C) ppm, 126.8 (2C) ppm, 126.4 ppm, 124.9 (2C) ppm, 122.6 (2C) ppm, and 114.9 (2C) ppm, attributable to aromatic carbons.

3. Materials and Methods

All organic solvents and chemicals were bought from commercial sources (Merck, Sigma-Aldrich, St. Louis, MO, USA). TLC was used to monitor the reaction on silica gel 60 F254 plates, visualized via UV light. 1H and 13C NMR spectra were recorded on a Bruker AC 400 spectrometer in CDCl3. High-resolution mass spectra (HRMS) were obtained with a LTQ Orbitrap hybrid mass spectrometer with an electrospray ionization probe (Thermo Scientific, San Jose, CA, USA) by direct infusion from a pump syringe to confirm the correct molar mass and high purity of compounds. The Munz Köfler Bench System was used to measure the melting points. An “Elmasonic S 30/S 30 H UltraSonic Bath Cleaner” with an effective ultrasonic power of 80 W and a frequency of 47 kHz was used to perform the ultrasound-assisted reactions.
  • 3-(Aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazoline4a–c: To a solution of aromatic aldehyde 1a–c (1 mmol) and hydroxylamine hydrochloride 2 (1.2 mmol) in H2O (10 mL), SDIC (0.5 mmol) was added. The reaction mixture was sonicated for 10 min at 25 °C (TLC monitoring). 4-(Allyloxy)azobenzene 3 was then added sequentially, and the mixture was sonicated using an ultrasonic bath (47 kHz) for 15 to 20 min (TLC monitoring). The mixture was extracted using CH2Cl2 (2 × 15 mL) and washed with saturated brine solution (15 mL × 2) and water (20 mL), dried over Na2SO4, and concentrated in vacuum. To obtain the pure azo-isoxazolines 4a–c, the residue was purified by recrystallization in EtOH, by dissolving the crude product in heated ethanol (10 mL). Then, the mixture was cooled down and the pure azo-isoxazolines 4a–c were isolated by filtration.
  • 3-(4-Methylphenyl)-5-((4-(phenyldiazenyl)phenoxy)methyl)-isoxazoline (4a): Yellow solid, yield 90%, m.p. 124–125 °C, TLC (cyclohexane/AcOEt, 5/5, v/v) Rf = 0.48; 1H NMR (400 MHz, CDCl3) δ 7.99–7.95 (m, 2H, HAr), 7.94–7.91 (m, 2H, HAr), 7.63 (d, J = 8.2 Hz, 2H, HAr), 7.56–7.50 (m, 2H, HAr), 7.49–7.45 (m, 1H, HAr), 7.28–7.24 (m, 2H, HAr), 7.06 (d, J = 9.0 Hz, 2H, HAr), 5.22–5.11 (m, 1H, C5H isoxazoline), 4.28 (dd, J = 9.8, 5.0 Hz, 1H, N-CH), 4.18 (dd, J = 9.9, 5.6 Hz, 1H, N-CH), 3.57 (dd, J = 16.7, 10.7 Hz, 1H, C4H isoxazoline), 3.42 (dd, J = 16.7, 6.9 Hz, 1H, C4H isoxazoline), 2.42 (s, 3H, CH3). 13C NMR (101 MHz, CDCl3) δ 160.9, 156.4, 152.5, 147.2, 140.6, 130.6, 129.5 (2C), 129.1 (2C), 126.8 (2C), 126.4, 124.9 (2C), 122.6 (2C), 114.9 (2C), 78.4, 68.9, 37.8, 21.5; HRMS: Calcd. for C23H21N3O2H+ ([M + H]+): 372.1634, Found: 372.1692.
  • 3-(4-Chlorophenyl)-5-((4-(phenyldiazenyl)phenoxy)methyl)-isoxazoline (4b): Yellow solid, yield 80%, m.p. 130–132 °C, TLC (cyclohexane/AcOEt, 5/5, v/v) Rf = 0.5; 1H NMR (400 MHz, CDCl3) δ 7.95 (d, J = 9.0 Hz, 2H, HAr), 7.93–7.89 (m, 2H, HAr), 7.67 (d, J = 8.6 Hz, 2H, HAr), 7.56–7.50 (m, 2H, HAr), 7.48 (d, J = 7.3 Hz, 1H, HAr), 7.43 (d, J = 8.6 Hz, 2H, HAr), 7.05 (d, J = 9.0 Hz, 2H, HAr), 5.24–5.15 (m, 1H, C5H isoxazoline), 4.29 (dd, J = 9.9, 4.8 Hz, 1H, N-CH), 4.19 (dd, J = 9.9, 5.4 Hz, 1H, N-CH), 3.55 (dd, J = 16.8, 10.8 Hz, 1H, C4H isoxazoline), 3.42 (dd, J = 16.7, 7.1 Hz, 1H, C4H isoxazoline). 13C NMR (101 MHz, CDCl3) δ 160.8, 155.3, 152.6, 147.1, 136.0, 130.6, 129.1 (2C), 129.1 (2C), 128.0 (2C), 127.8, 124.8 (2C), 122.6 (2C), 114.9 (2C), 78.9, 68.7, 37.4; HRMS: Calcd. for C22H18ClN3O2H+: ([M + H]+): 392.1088, Found: 392.1142.
  • 3-(4-Fluorophenyl)-5-((4-(phenyldiazenyl)phenoxy)methyl)-isoxazoline (4c): Yellow solid, yield 75%, m.p. 135–137 °C, TLC (cyclohexane/AcOEt, 6/4, v/v) Rf = 0.6; 1H NMR (400 MHz, CDCl3) δ 7.95 (d, J = 9.0 Hz, 2H, HAr), 7.93–7.88 (m, 2H, HAr), 7.76–7.69 (m, 2H, HAr), 7.56–7.50 (m, 2H, HAr), 7.49–7.44 (m, 1H, HAr), 7.18–7.11 (m, 2H, HAr), 7.05 (d, J = 9.0 Hz, 2H, HAr), 5.23–5.14 (m, 1H, C5H isoxazoline), 4.28 (dd, J = 9.9, 4.9 Hz, 1H, N-CH), 4.18 (dd, J = 9.9, 5.6 Hz, 1H, N-CH), 3.56 (dd, J = 16.7, 10.7 Hz, 1H, C4H isoxazoline), 3.42 (dd, J = 16.7, 7.0 Hz, 1H, C4H isoxazoline). 13C NMR (101 MHz, CDCl3) δ 163.89 (d, J = 250.9 Hz), 160.8, 155.5, 152.6, 147.4, 130.6, 129.1 (2C), 128.8, 128.7, 125.5 (d, J = 3.6 Hz), 124.8 (2C), 122.6 (2C), 116.1, 115.9, 114.9 (2C), 78.7, 68.7, 37.7.; HRMS: Calcd. for C22H18FN3O2H+: ([M + H]+): 376.1383, Found: 376.1440.

4. Conclusions

In conclusion, a simple and green one-pot three-component approach was developed for the synthesis of three novel azo-isoxazoline derivatives from aromatic aldehydes, hydroxylamine hydrochloride, and 4-(allyloxy)azobenzene. The benefits of this approach include the use of readily available raw materials, atom economy, a green solvent, process simplification, and straightforward target product isolation. In addition, the chemical structures of azo-isoxazolines (4a–c) were confirmed using spectroscopy techniques such as 1H NMR, 13C NMR, and HRMS.

Supplementary Materials

The following supporting information can be downloaded online. Figure S1: 1H NMR spectrum of 4a; Figure S2: 13C NMR spectrum of 4a; Figure S3: 1H NMR spectrum of 4b; Figure S4: 13C NMR spectrum of 4b; Figure S5: 1H NMR spectrum of 4c; Figure S6: 13C NMR spectrum of 4c; Figure S7: HRMS spectrum of 4a; Figure S8: HRMS spectrum of 4b; Figure S9: HRMS spectrum of 4c.

Author Contributions

Conceptualization, methodology, writing—original draft preparation, A.E.M., K.K., H.T. and K.B.; investigation, writing—review and editing, K.K.; supervision, funding acquisition, K.B. All authors have read and agreed to the published version of the manuscript.

Funding

This research received no external funding.

Data Availability Statement

Not applicable.

Acknowledgments

This work was supported by UM5R and UM6P. The authors thank UATRS-CNRST Morocco.

Conflicts of Interest

The authors declare no conflict of interest.

Sample Availability

Samples of the compounds are available from the authors.

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Molbank 2022 m1529 sch001 550
Scheme 1. Synthesis of 3-(aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines 4a–c.
Scheme 1. Synthesis of 3-(aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines 4a–c.
Molbank 2022 m1529 sch001
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MDPI and ACS Style

El Mahmoudi, A.; Karrouchi, K.; Tachallait, H.; Bougrin, K. Ultrasound Assisted One-Pot Synthesis of Novel 3-(Aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines in Water. Molbank 2022, 2022, M1529. https://doi.org/10.3390/M1529

AMA Style

El Mahmoudi A, Karrouchi K, Tachallait H, Bougrin K. Ultrasound Assisted One-Pot Synthesis of Novel 3-(Aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines in Water. Molbank. 2022; 2022(4):M1529. https://doi.org/10.3390/M1529

Chicago/Turabian Style

El Mahmoudi, Ayoub, Khalid Karrouchi, Hamza Tachallait, and Khalid Bougrin. 2022. "Ultrasound Assisted One-Pot Synthesis of Novel 3-(Aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines in Water" Molbank 2022, no. 4: M1529. https://doi.org/10.3390/M1529

APA Style

El Mahmoudi, A., Karrouchi, K., Tachallait, H., & Bougrin, K. (2022). Ultrasound Assisted One-Pot Synthesis of Novel 3-(Aryl)-5-((4-(phenyldiazenyl)phenoxy)methyl)isoxazolines in Water. Molbank, 2022(4), M1529. https://doi.org/10.3390/M1529

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