Home Physical Sciences Solvent-free preparation of 3-aryl-2-[(aryl)(arylamino)]methyl-4H-furo[3,2-c]chromen-4-one derivatives using ZnO-ZnAl2O4 nanocomposite as a heterogeneous catalyst
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Solvent-free preparation of 3-aryl-2-[(aryl)(arylamino)]methyl-4H-furo[3,2-c]chromen-4-one derivatives using ZnO-ZnAl2O4 nanocomposite as a heterogeneous catalyst

  • Hassan Abbasi-Dehnavi and Majid Ghashang ORCID logo EMAIL logo
Published/Copyright: January 5, 2018
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Heterocyclic Communications
From the journal Heterocyclic Communications Volume 24 Issue 1

Abstract

The title compounds were synthesized by a three-component reaction of 4-hydroxycoumarin, aromatic amines and α,β-epoxy ketones, catalyzed by ZnO-ZnAl2O4 nanocomposite.

Keywords: α,β-epoxy ketones; 4-hydroxycoumarin; furo[3,2-c]chromen-4-one; multi-component reaction; ZnO-ZnAl2O4 nano-composite

Introduction

Few reports have been published on the synthesis of furo[3,2-c]chromen-4-one derivatives. These compounds are known for their antimicrobial [1], anti-inflammatory [2], antiviral [3] and antibacterial activities and are DNA intercalating agents [4]. Their synthesis involves a four-component reaction of nitrostyrenes, aromatic aldehydes, coumarins and ammonium acetate [5], a Bu3P-mediated C-acylation/cyclization approach [6], a three-component reaction of 2,4′-dibromoacetophenone, benzaldehydes and 4-hydroxycoumarin under microwave irradiation [7], radical cyclization of hydroxyenones with electron-rich alkenes [8] and a Pd-catalyzed cascade of 1,4-addition and cyclization [9], among others. The three-component reaction of aromatic amines, 4-hydroxycoumarin and α,β-epoxy ketones leading to the formation of 3-aryl-2-[(aryl)-(arylamino)]methyl-4H-furo[3,2-c]chromen-4-ones, as reported in this paper, has not been previously described. This work is a continuation of our efforts devoted to the improved synthesis of heterocyclic motifs [10], [11], [12], [13], [14], [15], [16], [17], [18], [19], [20], [21], [22].

Results and discussion

ZnO-ZnAl2O4 nanocomposite was prepared through co-precipitation from an equimolar solution of zinc acetate and aluminum nitrate. The surface morphology and particle size analysis were performed using field emission-scanning electron microscopy (FE-SEM) and dynamic light scattering (DLS) techniques and the results are shown in Figure 1. FE-SEM images show that the nanocomposite is composed of amorphous particles and is a homogenized mixture of ZnO and ZnAl2O4 phases. The prepared nanoparticles were evaluated by X-ray diffraction (XRD). Although the broad peaks of zinc aluminate cover the peaks of zinc oxide, the XRD pattern is consistent with the formation of the two-phase nano-zinc oxide and zinc aluminate. The hexagonal phase of ZnO is characterized by peaks at 31.8, 34.3, 36.5, 47.6, 57.2, 63.2 and 67.9 [2θ°]. Zinc aluminate is characterized by peaks at 31.4, 36.8, 44.8, 47.6, 49.2, 55.7, 59.6, 62.7, 65.2 and 77.5 [2θ°], which shows a cubic phase.

Figure 1 XRD pattern, FE-SEM photographs and particle size distribution of ZnO-ZnAl2O4 nanocomposite.
Figure 1

XRD pattern, FE-SEM photographs and particle size distribution of ZnO-ZnAl2O4 nanocomposite.

The DLS technique was used to determine the particle size distribution. The results show that the samples consist of particles <100 nm in size. Before analysis, the sample was dispersed in ethanol (1 g in 25 mL) and sonicated for 30 min. The mean particle size determined by this method was 56 nm.

The condensation reaction of phenyl(3-phenyloxiran-2-yl)methanone (3a, 1 mmol), 4-hydroxycoumarin (2, 1 mmol) and aniline (1, 1 mmol) in the presence of the catalyst (Scheme 1) was investigated as a model reaction under solvent-free conditions and in different solvents including H2O, EtOH, aqueous EtOH (50%), n-hexane and CH2Cl2. The temperature and the amount of catalyst were also varied. In solution, the reaction was successful only in aqueous ethanol, furnishing the product in a 22% yield. Under optimized conditions, the solvent-free reaction leading to 4a was conducted at 120°C. Following these optimization studies, various derivatives of the 3-aryl-2-[(aryl)(arylamino)]methyl-4H-furo[3,2-c]chromen-4-ones were prepared. In all cases, the reaction proceeded well and the products were obtained in moderate to good yields.

Scheme 1 Catalytic three-component reactions of aromatic amines, 4-hydroxycoumarin and α,β-epoxy ketones using ZnO-ZnAl2O4 nanocomposite as a catalyst.
Scheme 1

Catalytic three-component reactions of aromatic amines, 4-hydroxycoumarin and α,β-epoxy ketones using ZnO-ZnAl2O4 nanocomposite as a catalyst.

Finally, the catalyst was recovered from the reaction medium by filtration and used for new reactions. It was found that the catalyst could be reused for five successive runs without loss of its catalytic activity.

Conclusion

A novel one-pot three-component reaction of aromatic amines, 4-hydroxycoumarin and α,β-epoxy ketones under solvent-free conditions at 120°C in the presence of ZnO-ZnAl2O4 nanocomposite as a heterogeneous catalyst furnishes furo[3,2-c]chromen-4-ones 4a–i.

Experimental

The powder XRD patterns were measured with a D8-Advance diffractometer (Bruker) using Cu-Kα irradiation. The 1H nuclear magnetic resonance (NMR) (400 MHz) and 13C NMR (100 MHz) spectra were recorded on a Bruker Avance DPX 400 instrument. The spectra were measured in dimethyl sulfoxide-d6 (DMSO-d6) relative to tetramethylsilane (TMS). Elemental analysis was performed on a Heraeus CHN-O-Rapid analyzer. The powder XRD patterns were measured with a D8-Advance diffractometer (Bruker) using Cu-Kα irradiation. FE-SEM and energy dispersive X-ray analysis measurements were taken on a Hitachi S-4160 instrument to examine the shape and metallic composition of the samples.

Preparation of ZnO-ZnAl2O4 nanocomposite

Zinc acetate (20 mmol) and aluminum nitrate (20 mmol) were dissolved in 100 mL of water in a 250-mL beaker (solution A). In a separate beaker, 2-aminoethanol (120 mmol) was dissolved in a mixture of water (50 mL) and glycerine (10 mL) (solution B). Solution B was slowly added dropwise to the solution A under vigorous magnetic stirring. The mixture was continuously stirred for another 60 min. The resulting precipitate was filtered, washed with water several times, dried in an oven and finally calcined at 700°C for 2 h.

Preparation of compounds 4a–i

A mixture of aromatic amine 1 (1.0 mmol), 4-hydroxycoumarin (2, 1.0 mmol), α,β-epoxy ketone 3 (1 mmol) and ZnO-ZnAl2O4 nanocomposite (0.025 g) was heated at 120°C for 3 h. After the completion of the reaction, as monitored by thin-layer chromatography (TLC) eluting with EtOAc/hexane (1:9), the resultant solid was dissolved in hot ethanol, and the solution was filtered and concentrated. The product 4a–i was crystallized from ethanol.

3-Phenyl-2-[(phenyl)(phenylamino)]methyl-4H-furo[3,2-c]chromen-4-one (4a)

Yield 69%; mp 257–259°C; 1H NMR: δ 4.22 (s, 1H, NH), 6.19 (s, 1H, CH), 6.89 (t, 1H, J=7.8 Hz), 7.06–7.67 (m, 17H), 7.83 (d, 1H, J=8.2 Hz) ); 13C NMR: δ 58.3, 113.7, 114.2, 114.8, 117.1, 123.6, 123.9, 124.7, 126.9, 127.4, 128.2, 128.5, 128.9, 129.1, 129.2, 129.5, 131.3, 132.8, 139.6, 143.7, 151.6, 152.9, 158.6, 160.1. Anal. Calcd for C30H21NO3: C, 81.25; H, 4.77; N, 3.16%. Found: C, 81.19; H, 4.68; N, 3.14.

3-Phenyl-2-[(phenyl)(2,4-dichlorophenylamino)]methyl-4H-furo[3,2-c]chromen-4-one (4b)

Yield 22%; mp >300°C; 1H NMR: δ 4.37 (s, 1H, NH), 6.15 (s, 1H, CH), 6.97 (d, 1H, J=7.8 Hz), 7.10–7.62 (m, 15H), 7.81 (d, 1H, J=8.4 Hz) ); 13C NMR: δ 58.6, 114.1, 114.8, 117.0, 117.2, 122.9, 123.5, 123.9, 126.9, 127.4, 128.2, 128.5, 128.8, 129.1, 129.2, 129.4, 130.6, 131.3, 132.8, 135.3, 139.7, 151.5, 152.9, 158.5, 159.9. Anal. Calcd for C30H19Cl2NO3: C, 70.32; H, 3.74; N, 2.73. Found: C, 70.19; H, 3.68; N, 2.63.

3-Phenyl-2-[(phenyl)(4-nitrophenylamino)]methyl-4H-furo[3,2-c]chromen-4-one (4c)

Yield 50%; mp >300°C; 1H NMR: δ 4.89 (s, 1H, NH), 6.19 (s, 1H, CH), 7.07–7.62 (m, 15H), 7.82 (d, 1H, J=8.4 Hz), 8.09 (d, 2H, J=8.0 Hz); 13C NMR: δ 58.9, 113.9, 114.6, 116.9, 117.3, 118.8, 123.4, 123.8, 126.9, 127.4, 128.4, 128.5, 128.9, 129.1, 129.4, 131.5, 132.7, 139.5, 140.7, 144.1, 151.6, 152.8, 158.7, 160.4 Anal. Calcd for C30H20N2O5: C, 73.76; H, 4.13; N, 5.73. Found: C, 73.63; H, 4.01; N, 5.67.

3-Phenyl-2-[(phenyl)(cyclohexylamino)]methyl-4H-furo[3,2-c]chromen-4-one (4d)

Yield 43%; mp 203–205°C; 1H NMR: δ 1.25–1.71 (m, 10H), 2.61–2.64 (m, 1H), 4.02 (s, 1H, NH), 6.01 (s, 1H, CH), 7.16–7.66 (m, 13H), 7.82 (d, 1H, J=8.3 Hz); 13C NMR: δ 25.3, 26.4, 34.7, 53.9, 58.3, 113.7, 114.0, 116.9, 123.5, 123.9, 126.9, 127.7, 128.2, 128.5, 128.8, 129.0, 129.4, 131.5, 132.7, 139.4, 151.5, 152.7, 158.6, 159.8. Anal. Calcd for C30H27NO3: C, 80.15; H, 6.05; N, 3.12. Found: C, 80.19; H, 6.05; N, 3.14.

3-Phenyl-2-[(phenyl)(2-methoxyphenylamino)]methyl-4H-furo[3,2-c]chromen-4-one (4e)

Yield 57%; mp 237–239°C; 1H NMR: δ 3.81 (s, 3H, OCH3), 4.19 (s, 1H, NH), 6.13 (s, 1H, CH), 6.84–6.99 (m, 4H), 7.14–7.66 (m, 13H), 7.82 (d, 1H, J=8.4 Hz); 13C NMR: δ 56.3, 58.4, 110.9, 114.0, 114.5, 116.8, 118.1, 121.9, 123.4, 123.5, 123.8, 127.0, 127.1, 127.4, 127.6, 128.5, 128.7, 128.9, 129.0, 129.3, 131.5, 132.8, 139.5, 147.8, 151.6, 152.6, 158.5, 160.1. Anal. Calcd for C31H23NO4: C, 78.63; H, 4.90; N, 2.96. Found: C, 78.51; H, 4.77; N, 2.88.

3-(4-Chlorophenyl)-2-[(phenyl)(phenylamino)]methyl-4H-furo[3,2-c]chromen-4-one (4f)

Yield 76%; mp 276–278°C; 1H NMR: δ 4.23 (s, 1H, NH), 6.10 (s, 1H, CH), 6.89 (t, 1H, J=7.8 Hz), 7.02–7.54 (m, 16H), 7.80 (d, 1H, J=8.6 Hz); 13C NMR: δ 58.3, 113.4, 113.8, 114.1, 116.7, 123.2, 123.7, 124.7, 126.9, 128.3, 128.5, 128.9, 129.1, 129.2, 129.5, 131.5, 132.8, 135.7, 139.4, 144.0, 151.5, 152.3, 158.7, 160.2. Anal. Calcd for C30H20ClNO3: C, 75.39; H, 4.22; N, 2.93. Found: C, 75.33; H, 4.16; N, 2.85.

3-(4-Chlorophenyl)-2-[(phenyl)(p-tolylamino)]methyl-4H-furo[3,2-c]chromen-4-one (4g)

Yield 77%; mp 283–285°C; 1H NMR: δ 2.19 (s, 3H, CH3), 4.28 (s, 1H, NH), 6.07 (s, 1H, CH), 6.68 (d, 2H, J=7.8 Hz), 7.06 (d, 2H, J=7.8 Hz), 7.11–7.54 (m, 12H), 7.81 (d, 1H, J=8.4 Hz); 13C NMR: δ 21.4, 58.4, 113.8, 114.3, 114.3, 116.6, 123.4, 123.6, 126.9, 128.4, 128.7, 128.9, 129.2, 129.5, 129.6, 131.5, 132.5, 132.7, 135.6, 139.5, 144.1, 151.6, 152.3, 158.7, 160.1. Anal. Calcd for C31H22ClNO3: C, 75.68; H, 4.51; N, 2.85. Found: C, 75.60; H, 4.46; N, 2.79.

3-(4-Chlorophenyl)-2-[(phenyl)(4-methoxyphenylamino)]methyl-4H-furo[3,2-c]chromen-4-one (4h)

Yield 83%; mp 288–290°C; 1H NMR: δ 3.74 (s, 3H, OCH3), 4.23 (s, 1H, NH), 6.06 (s, 1H, CH), 6.85 (d, 2H, J=7.8 Hz), 6.97 (d, 2H, J=7.8 Hz), 7.11–7.54 (m, 12H), 7.81 (d, 1H, J=8.4 Hz); 13C NMR: δ 56.1, 58.4, 113.9, 114.2, 114.4, 116.3, 116.6, 123.4, 123.6, 126.9, 128.4, 128.7, 128.9, 129.5, 129.6, 131.5, 132.7, 135.7, 139.5, 144.1, 151.6, 152.3, 157.7, 158.6, 160.2. Anal. Calcd for C31H22ClNO4: C, 73.30; H, 4.37; N, 2.76. Found: C, 73.30; H, 4.37; N, 2.76.

3-(4-Chlorophenyl)-2-[(phenyl)(4-chlorophenylamino)]methyl-4H-furo[3,2-c]chromen-4-one (4i)

Yield 70%; mp >300°C; 1H NMR: δ 4.39 (s, 1H, NH), 6.10 (s, 1H, CH), 6.52 (d, 2H, J=7.6 Hz), 7.12–7.54 (m, 14H), 7.81 (d, 1H, J=8.6 Hz); 13C NMR: δ 58.5, 113.9, 114.4, 116.5, 119.8, 123.2, 123.8, 126.9, 128.4, 128.8, 129.0, 129.2, 129.4, 129.6, 130.0, 131.4, 132.8, 135.9, 139.7, 144.1, 151.5, 152.4, 158.7, 160.2. Anal. Calcd for C30H19Cl2NO3: C, 70.32; H, 3.74; N, 2.73. Found: C, 70.27; H, 3.68; N, 2.70.

Acknowledgments

We are thankful to the Najafabad Branch of the Islamic Azad University Research Council for partial support of this research.

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Received: 2017-08-06
Accepted: 2017-11-03
Published Online: 2018-01-05
Published in Print: 2018-02-23

©2018 Walter de Gruyter GmbH, Berlin/Boston

Articles in the same Issue

  1. Frontmatter
  2. Review
  3. Research progress in quinazoline derivatives as multi-target tyrosine kinase inhibitors
  4. Research Articles
  5. A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles
  6. Solvent-free preparation of 3-aryl-2-[(aryl)(arylamino)]methyl-4H-furo[3,2-c]chromen-4-one derivatives using ZnO-ZnAl2O4 nanocomposite as a heterogeneous catalyst
  7. Synthesis of 4-arylethyl-6-arylpyrimidine-2-thiols through aza-Michael addition/nucleophilic addition/aromatization tandem reactions
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  9. Synthesis of new 3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement
  10. A new synthesis of pyrrolo[3,2-d]pyrimidine derivatives by a one-pot, three-component reaction in the presence of L-proline as an organocatalyst
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  12. Synthesis, crystal structure, molecular docking studies and bio-evaluation of some N4-benzyl-substituted isatin- 3-thiosemicarbazones as urease and glycation inhibitors
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https://doi.org/10.1515/hc-2017-0141
Keywords for this article
α,β-epoxy ketones; 4-hydroxycoumarin; furo[3,2-c]chromen-4-one; multi-component reaction; ZnO-ZnAl2O4 nano-composite

Articles in the same Issue

  1. Frontmatter
  2. Review
  3. Research progress in quinazoline derivatives as multi-target tyrosine kinase inhibitors
  4. Research Articles
  5. A bio-inspired approach to proline-derived 2,4-disubstituted oxazoles
  6. Solvent-free preparation of 3-aryl-2-[(aryl)(arylamino)]methyl-4H-furo[3,2-c]chromen-4-one derivatives using ZnO-ZnAl2O4 nanocomposite as a heterogeneous catalyst
  7. Synthesis of 4-arylethyl-6-arylpyrimidine-2-thiols through aza-Michael addition/nucleophilic addition/aromatization tandem reactions
  8. 3-Carboxy-1-sulfopyridin-1-ium chloride ([CPySO3H]+Cl−): an efficient catalyst for one-pot synthesis of hexahydroquinoline-3-carboxamides
  9. Synthesis of new 3H-chromeno[2,3-d]pyrimidine-4,6(5H,7H)-diones via the tandem intramolecular Pinner/Dimroth rearrangement
  10. A new synthesis of pyrrolo[3,2-d]pyrimidine derivatives by a one-pot, three-component reaction in the presence of L-proline as an organocatalyst
  11. Diversity-oriented synthesis of amide derivatives of tricyclic thieno[2,3-d]pyrimidin-4(3H)-ones and evaluation of their influence on melanin synthesis in murine B16 cells
  12. Synthesis, crystal structure, molecular docking studies and bio-evaluation of some N4-benzyl-substituted isatin- 3-thiosemicarbazones as urease and glycation inhibitors
  13. Ultrasound-assisted synthesis and antimicrobial activity of tetrazole-based pyrazole and pyrimidine derivatives
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