Skip to content
BY-NC-ND 3.0 license Open Access Published by De Gruyter November 14, 2017

Efficient synthesis of new pyrano[3,2-b]pyran derivatives via Fe3O4@SiO2-IL-Fc catalyzed three-component reaction

  • Reza Teimuri-Mofrad EMAIL logo , Somayeh Esmati , Masoumeh Rabiei and Mahdi Gholamhosseini-Nazari


Ferrocene-containing ionic liquid supported on silica-coated Fe3O4 magnetic nanoparticles (nano Fe3O4@SiO2-IL-Fc), a novel heterogeneous nanocatalyst, was synthesized. The structure of the catalyst was characterized by Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction patterns (XRD), energy-dispersive X-ray spectroscopy (EDX) and field emission scanning electron microscopy (FE-SEM). The novel nanomagnetic catalyst was used in the one-pot synthesis of pyrano[3,2-b]pyran derivatives by the three-component reaction of various aldehydes, malononitrile and kojic acid or chlorokojic acid at room temperature under ultrasonic irradiation. This new method has many advantages such as simplicity, short reaction times, high yields, easy workup and easy purification. Also, the nanocatalyst can be separated on an external magnet and reused for at least six consecutive runs without any significant loss of its catalytic activity.


Synthesis of efficient and recyclable catalysts has been an increasingly important goal for chemists and material scientists for both economic and environmental reasons [1], [2]. In this regard, magnetic nanoparticles (MNPs) have been widely used as catalysts due to their high surface area, easy synthesis and functionalization, good stability, low toxicity and facile separation by an external magnetic force [3], [4], [5], [6]. Recent investigations have revealed that MNPs can act as excellent supports for various homogeneous catalysts, and diverse organic transformations catalyzed by supported MNPs have been reported [7]. Besides, supported ionic liquids (SILs) are an important class of heterogeneous catalysts and have many advantages over free ILs, including a higher number of accessible active sites on the catalyst, reduction in the amount of required IL and improved recyclability of catalysts [8]. Ferrocene containing SILs have been synthesized and used in some organic reactions [9], [10], but the development andexpansion of these types of catalysts needs more attention.

Pyran derivatives are important structural units of many natural products and synthetic compounds which possess a wide range of pharmacological and biological activities such as anti-HIV [11], anticancer [12], [13], antimicrobial [14], antifungal [15], antidiabetic [16], antiviral and anti-inflammatory [17] and antioxidant [18] properties, among others [19], [20], [21], [22]. Pyrano[3,2-b]pyrans are of great interest in organic synthesis, and various methods using different homogeneous and heterogeneous catalysts have been reported for the preparation of these compounds and analogues [23], [24], [25], [26], [27], [28], [29].

In continuation of our research on the synthesis and applications of ferrocene derivatives [30], [31] and the development of multicomponent reactions [32], [33], [34], [35], herein we report the design and synthesis of novel ferrocene labeled ionic liquid supported on MNPs as an efficient catalyst for the synthesis of a series of pyrano[3,2-b]pyran derivatives under ultrasound irradiation.

Results and discussion

The ferrocene functionalized ionic liquid supported on magnetic nanoparticle (Fe3O4@SiO2-IL-Fc) as the catalyst was prepared according to Scheme 1. A chemical co-precipitation method was used for the preparation of nanomagnetite (Fe3O4). Subsequently, Fe3O4 nanoparticles were covered with silica (Fe3O4@SiO2) using the Stober method [36]. The silica-coated MNPs were subsequently allowed to react with (3-chloropropyl)triethoxysilane to obtain the functionalized nanoparticles. Then, 1-(4-ferrocenylbutyl)-1H-imidazole was prepared by the reaction of imidazole with 4-chlorobutylferrocene. Finally, ferrocene containing ionic liquid supported on MNPs was synthesized by the reaction of chloropropyl functionalized silica-coated MNPs with 1-(4-ferrocenylbutyl)-1H-imidazole.

Scheme 1 Preparation of Fe3O4@SiO2-IL-Fc nanocatalyst.
Scheme 1

Preparation of Fe3O4@SiO2-IL-Fc nanocatalyst.

The nanomagnetic Fe3O4 particles show the IR absorption peak at about 572 cm−1 which is related to Fe-O bond vibrations. The Fe3O4@SiO2-propyl chloride core-shell MNPs show the Fe-O and Si-O-Si bonds IR vibrations, and the absorption peak at 2925 cm−1 is related to the asymmetric stretching vibration of aliphatic C-H moieties. Finally, in the infrared (IR) spectrum of the Fe3O4@SiO2-IL-Fc MNPs, absorption peak above 3000 cm−1 is related to the stretching vibration of aromatic C-H moieties of imidazole and ferrocene groups. The absorption peak at 1644 and 1385 cm−1 are linked to the stretching vibrations of C=N and C=C bonds of aromatic rings.

The energy-dispersive X-ray spectrum of the Fe3O4@SiO2-IL-Fc nanocatalyst is consistent with the presence of the expected elements (Fe, Cl, Si, O, N and C) in the structure. The X-ray diffraction (XRD) analyses illustrate the degree of crystallinity of the synthesized Fe3O4@SiO2-IL-Fc nanocatalyst. The XRD pattern of Fe3O4@SiO2-IL-Fc is the same as that of Fe3O4 and shows diffraction peaks at 2θ=30.4°, 35.7°, 43.3°, 53.9°, 57.3° and 63.0°. These results indicate that the functionalization process did not induce any phase change of Fe3O4. The surface morphology of the nanoparticles was investigated by field emission scanning electron microscopy (FE-SEM) analysis. The FE-SEM images show that the particles are uniformly distributed and the sizes of MNPs are under 60 nm.

For optimization of the catalyst and reaction conditions, the reaction of 4-methylbenzaldehyde (1 mmol), malononitrile (1.2 mmol) and kojic acid (1 mmol) was selected. Initially, the model reaction was examined with some catalysts including typical ILs, ferrocene labeled IL and newly synthesized Fe3O4@SiO2-IL-Fc nanocatalyst under solvent-free conditions at 80°C. It was found that Fe3O4@SiO2-IL-Fc shows the best catalytic activity. Different solvents including CH2Cl2, CH3CN, EtOH and H2O were examined in the presence of Fe3O4@SiO2-IL-Fc as catalyst. For the reaction conducted in ethanol or aqueous ethanol the product 4a is obtained rapidly and in high yield. However, the best yield of 95% is obtained in aqueous ethanol containing 30% of water under ultrasonic irradiation. The amount of the catalyst under optimized conditions is 6 mg per 1 mmol of the aldehyde. Different aromatic aldehydes were allowed to react under this optimal procedure with ultrasonic irradiation. The results are summarized in Scheme 2. The reactions of aromatic aldehydes with both electron-releasing and electron-withdrawing substituents furnish the corresponding 2-aminopyrano[3,2-b]pyrans 4 in good to high yields under the optimized conditions. Aldehydes with electron-withdrawing substituents react more rapidly, while electron donating substituents decrease the reactivity and the reactions are completed at longer reaction times.

Scheme 2 Fe3O4@SiO2-IL-Fc catalyzed three-component synthesis of pyrano[3,2-b]pyran derivatives in EtOH/H2O (70:30) at room temperature under ultrasonic irradiation.
Scheme 2

Fe3O4@SiO2-IL-Fc catalyzed three-component synthesis of pyrano[3,2-b]pyran derivatives in EtOH/H2O (70:30) at room temperature under ultrasonic irradiation.

Chlorokojic acid (5) was also subjected to this reaction under optimized conditions and the target compounds 6a–f were synthesized in high yields (Scheme 3). All products 4 and 6 were characterized by melting points, IR, 1H nuclear magnetic resonance (NMR), 13C NMR and elemental analysis.

Scheme 3 Synthesis of pyrano[3,2-b]pyran derivatives 6a–f.
Scheme 3

Synthesis of pyrano[3,2-b]pyran derivatives 6a–f.

A possible mechanism for the Fe3O4@SiO2-IL-Fc catalyzed condensation reaction is proposed in Scheme 4. The first step is the Knoevenagel condensation of aromatic aldehyde and malononitrile to generate the intermediate product (A). Then, the Michael addition of (chloro)kojic acid enolate (B) with (A) furnishes an intermediate product (C), which undergoes cyclization to (D). The intermediate product (D) is a direct precursor to the final pyrano[3,2-b]pyran product.

Scheme 4 Proposed mechanism for the Fe3O4@SiO2-IL-Fc catalyzed three-component reaction.
Scheme 4

Proposed mechanism for the Fe3O4@SiO2-IL-Fc catalyzed three-component reaction.

The reusability of the magnetic nanocatalyst was investigated using the model reaction leading to 4a. After completion of the reaction, the catalyst was separated with an external magnet. The collected nanocatalyst was repeatedly washed with EtOH prior to use in the next round of catalysis. The catalyst exhibited a consistent activity up to the sixth consecutive cycle. Specifically, the yield of 4a of 95% after the first cycle was only lowered to 90% after the sixth cycle and the initial reaction time of 10 min had to be increased to 12 min to complete the reaction.


A simple, rapid and efficient method for the three-component synthesis of pyrano[3,2-b]pyran derivatives using a novel Fe3O4 supported ionic liquid phase catalyst with a ferrocenyl group under ultrasonic irradiation was developed. The protocol provides a practical benefit of facile removal of the catalyst that can subsequently be reused.


Melting points were measured with a MEL-TEMP model 1202D. Fourier transform infrared (FT-R) spectra were recorded on a Bruker Tensor 27 spectrometer using KBr disks. The 1H NMR spectra (400 MHz) were determined with a Bruker Spectrospin Avance 400 spectrometer with DMSO-d6 as a solvent and tetramethylsilane (TMS) as an internal standard. 13C NMR spectra were recorded on the same instrument at 100 MHz. Elemental analyses were performed on a Vario EL III analyzer. Sonication was performed using a Hielscher (UP400s) ultrasonic probe system at a frequency of 24 KHz. XRD patterns of samples were taken on a Siemens D500 X-ray powder diffraction diffractometer (CuK radiation, λ=1.5406 Å). FE-SEM images of the products were visualized with a TESCAN MIRA3 FE-SEM.

Synthesis of 1-(4-ferrocenylbutyl)-1H-imidazole

To a suspension of NaH (60%, 0.80 g, 20 mmol) in dry THF (100 mL), imidazole (1.36 g, 20 mmol) was added and the mixture was stirred at 0°C for 1 h. Then, 4-chlorobutylferrocene (1.38 g, 5 mmol) was added and the mixture was heated under reflux for 12 h. After cooling, the excess amount of NaH was quenched by the addition of water. After extraction with dichloromethane, the extract was concentrated and the residue was subjected to silica column chromatography eluting with n-hexane/ethyl acetate, 9:1, to give 1-(4-ferrocenylbutyl)-1H-imidazole as brown viscous oil; IR: 3394, 2859, 1506, 1453, 1105, 1228, 1000, 650, 486 cm−1; 1H NMR: δ 1.42–1.49 (m, 2H, -CH2-), 1.75–1.78 (m, 2H, -CH2-), 2.34 (t, J=7.5 Hz, 2H, -CH2-), 3.90 (t, J=6.6 Hz, 2H, -CH2-), 4.00–4.03 (m, 4H, Cp-H), 4.06 (s, 5H, Cp-H), 6.98–7.26 (m, 2H, imid-H), 7. 49 (s, 1H, imid-H); 13C NMR: δ 27.0, 28.0, 29.7, 45.9, 66.1, 66.9, 67.3, 87.0, 118.2, 128.7, 136.6 ppm.

Synthesis of Fe3O4@SiO2-IL-Fc

Fe3O4@SiO2-propyl chloride nanoparticales were prepared as previously reported [38], [39]. Then, a mixture of Fe3O4@SiO2-(CH2)3Cl (1.0 g) and 1-(4-ferrocenylbutyl)-1H-imidazole (0.92 g, 3 mmol) in 10 mL of toluene was heated at 80°C in an oil bath. After 72 h, the residue was filtered, washed with toluene (3×20 mL), MeOH (3×20 mL), CH2Cl2 (3×20 mL) and dried under reduced pressure at 50°C for 48 h to afford Fe3O4@SiO2-IL-Fc.

General procedure for the synthesis of pyrano[3,2-b]pyrans 4a–l and 6a–f

A 50-mL flask was charged with aldehyde (1 mmol), malononitrile (1.2 mmol), kojic acid or chlorokojic acid (1 mmol) and Fe3O4@SiO2-IL-Fc nanocatalyst (6 mg) in 3 mL EtOH/H2O (70:30). The mixture was sonicated at 25°C. When the reaction was completed [monitored by thin layer chromatography (TLC), using n-hexane/ethyl acetate (3:1) as eluent], the catalyst was separated using an external magnet and the reaction mixture was cooled and the precipitate was filtered, washed and dried. The crude product was crystallized from ethanol. The structures of new compounds 6a–f were characterized by IR, 1H NMR, 13C NMR and CHN analysis. The spectra for 4a–l were virtually identical with those reported (Scheme 2).

2-Amino-6-(chloromethyl)-4-(4-isopropylphenyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile (6a)

White powder; mp 207–209°C; IR: 3379, 3290, 3027, 2960, 2199, 1647, 1598 cm−1; 1H NMR: δ 1.18 (d, 6H, J=6.47 Hz, 2CH3), 2.84–2.90 (m, 1H, CH), 4.52–4.60 (m, 2H, CH2), 4.78 (s, 1H, methin-H), 6.59 (s, 1H, Ar-H), 7.18–7.27 (m, 6H, NH2, Ar-H); 13C NMR: δ 23.8, 33.1, 40.8, 41.2, 55.7, 114.9, 119.4, 126.9, 127.6, 136.5, 138.3, 148.0, 150.0, 159.2, 161.9, 169.6. Anal. Calcd for C19H17ClN2O3: C, 63.96; H, 4.80; N, 7.85. Found: C, 63.71; H, 4.84; N, 7.89.

2-Amino-6-(chloromethyl)-8-oxo-4-(p-tolyl)-4,8-dihydropyrano [3,2-b]pyran-3-carbonitrile (6b)

White powder; mp 236–238°C; IR: 3376, 3322, 3017, 2953, 2200, 1647, 1599 cm−1; 1H NMR: δ 2.28 (s, 3H, CH3), 4.51–4.59 (m, 2H, CH2), 4.78 (s, 1H, methin-H), 6.59 (s, 1H, Ar-H), 7.16 -7.21 (m, 4H, Ar-H), 7.25 (s, 2H, NH2); 13C NMR: δ 20.6, 39.6, 40.8, 55.7, 114.9, 119.2, 127.6, 129.5, 136.5, 137.1, 137.6, 149.9, 159.1, 161.8,169.4. Anal. Calcd for C17H13ClN2O3: C, 62.11; H, 3.99; N, 8.52. Found: C, 61.88; H, 4.03; N, 8.57.

2-Amino-6-(chloromethyl)-4-(4-nitrophenyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile (6c)

White powder; mp 193–195°C ; IR: 3400, 3300, 3084, 2924, 2197, 1642, 1591 cm−1; 1H NMR: δ 4.51–4.59 (m, 2H, CH2), 5.14 (s, 1H, methin-H), 6.62 (s, 1H, Ar-H), 7.42 (s, 2H, NH2), 7.64 (d, 2H, J=8.23 Hz, Ar-H), 8.26 (d, 2H, J=8.23 Hz, Ar-H); 13C NMR: δ 39.6, 40.8, 55.2, 114.9, 119.0, 128.9, 129.8, 132.6, 136.6, 139.5, 149.2, 159.1, 161.8, 169.4. Anal. Calcd for C16H10ClN3O5: C, 53.42; H, 2.80; N, 11.68. Found: C, 53.18; H, 2.83; N, 11.72.

2-Amino-6-(chloromethyl)-4-(3-nitrophenyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile (6d)

White powder; mp 208–210°C ; IR: 3395, 3325, 3080, 2957, 2191, 1638, 1597 cm−1; 1H NMR: δ 4.51–4.60 (m, 2H, CH2), 5.19 (s, 1H, methin-H), 6.62 (s, 1H, Ar-H), 7.43 (s, 2H, NH2), 7.71 (t, 1H, J=5.5 Hz, Ar-H), 7.83 (d, 1H, J=7.67 Hz, Ar-H), 8.21 (m, 2H, Ar-H); 13C NMR: δ 39.6, 40.8, 54.5, 115.0, 119.0, 122.7, 123.1, 130.7, 134.8, 136.8, 142.6, 148.0, 148.5, 159.4, 161.9, 169.5. Anal. Calcd for C16H10ClN3O5: C, 53.42; H, 2.80; N, 11.68. Found: C, 53.15; H, 2.84; N, 11.73.

2-Amino-6-(chloromethyl)-4-(4-chlorophenyl)-8-oxo-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile (6e)

White powder; mp 217–219°C; IR: 3374, 3312, 3028, 2958, 2198, 1641, 1594 cm−1; 1H NMR: δ 4.52–4.59 (m, 2H, CH2), 4.91 (s, 1H, methin-H), 6.60 (s, 1H, Ar-H), 7.32–7.36 (m, 4H, Ar-H and NH2), 7.46 (d, 2H, J=8.34 Hz, Ar-H); 13C NMR: δ 39.6, 40.7, 55.2, 114.9, 119.0, 128.9, 129.8, 132.6, 136.6, 139.5, 149.2, 159.1, 161.8, 169.4. Anal. Calcd for C16H10Cl2N2O3: C, 55.04; H, 2.89; N, 8.02. Found: C, 54.85; H, 2.92; N, 8.10.

2-Amino-6-(chloromethyl)-8-oxo-4-(thiophen-2-yl)-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile (6f)

White powder; mp 190–192°C ; IR: 3381, 3312, 3028, 2925, 2200, 1640, 1598 cm−1; 1H NMR: δ 4.58–4.65 (m, 2H, CH2), 5.21 (s, 1H, methin-H), 6.62 (s, 1H, Ar-H), 7.02 (t, J=4.39 Hz, 1H, Ar-H), 7.09 (s, 1H, Ar-H), 7.37 (s, 2H, NH2), 7.52 (d, J=4.75 Hz, 1H, Ar-H); 13C NMR: δ 35.5, 40.8, 55.6, 115.0, 119.0, 126.1, 126.4, 127.3, 135.9, 144.6, 149.1, 159.3, 161.9, 169.4. Anal. Calcd for C14H9ClN2O3S: C, 52.43; H, 2.83; N, 8.73. Found: C, 52.19; H, 2.87; N, 8.80.


The authors thank Research Affairs of the University of Tabriz for financial support.


[1] Rossi, L. M.; Silva, F. P.; Vono, L. L.; Kiyohara, P. K.; Duarte, E. L.; Itri, R.; Landers, R.; Machado, G. Superparamagnetic nanoparticle-supported palladium: a highly stable magnetically recoverable and reusable catalyst for hydrogenation reactions. Green Chem.2007, 9, 379–385.10.1039/b612980cSearch in Google Scholar

[2] Shahrisa, A.; Esmati, S. Three novel sequential reactions for the facile synthesis of a library of bisheterocyclespossessing the 3-aminoimidazo[1,2-a]pyridine core catalyzed by bismuth(III) chloride. Synlett2013, 24, 595–602.10.1055/s-0032-1318221Search in Google Scholar

[3] Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara, M.; Basset, J.-M. Magnetically recoverable nanocatalysts. Chem. Rev.2011, 111, 3036–3075.10.1021/cr100230zSearch in Google Scholar PubMed

[4] Gawande, M. B.; Branco, P. S.; Varma, R. S. Nano-magnetite (Fe3O4) as a support for recyclable catalysts in the development of sustainable methodologies. Chem. Soc. Rev.2013, 42, 3371–3393.10.1039/c3cs35480fSearch in Google Scholar PubMed

[5] Baig, R. N.; Varma, R. S. Organic synthesis via magnetic attraction: benign and sustainable protocols using magnetic nanoferrites. Green. Chem.2013, 15, 398–417.10.1002/chin.201320220Search in Google Scholar

[6] Sadeghzadeh, S. M.; Daneshfar, F.; Malekzadeh, M. Manganese(III) salen complex immobilized on Fe3O4magnetic nanoparticles: the efficient, green and reusable nanocatalyst. Chin. J. Chem.2014, 32, 349–355.10.1002/cjoc.201400007Search in Google Scholar

[7] Shylesh, S.; Schünemann, V.; Thiel, W. R. Magnetically separable nanocatalysts: bridges between homogeneous and heterogeneous catalysis. Angew. Chem. Int. Ed.2010, 49, 3428–3459.10.1002/anie.200905684Search in Google Scholar PubMed

[8] Xin, B.; Hao, J. Imidazolium-based ionic liquids grafted on solid surfaces. Chem. Soc. Rev.2014, 43, 7171–7187.10.1039/C4CS00172ASearch in Google Scholar PubMed

[9] Rashinkar, G.; Salunkhe, R. J. Ferrocene labelled supported ionic liquid phase (SILP) containing organocatalytic anion for multi-component synthesis. J. Mol. Catal. A-Chem.2010, 316, 146–152.10.1016/j.molcata.2009.10.013Search in Google Scholar

[10] Rashinkar, G.; Kamble, S.; Kumbhar, A.; Salunkhe, R. An expeditious synthesis of homoallylic alcohols using Brønsted acidic supported ionic liquid phase catalyst with pendant ferrocenyl group. Catal. Commun.2011, 12, 1442–1447.10.1016/j.catcom.2011.05.026Search in Google Scholar

[11] He, M.; Yang, N.; Sun, C.; Yao, X.; Yang, M. Modification and biological evaluation of novel 4-hydroxy-pyrone derivatives as non-peptidic HIV-1 protease inhibitors. Med. Chem. Res.2011, 20, 200–209.10.1007/s00044-010-9307-4Search in Google Scholar

[12] da Rocha, D. R.; de Souza, A. C.; Resende, J. A.; Santos, W. C.; dos Santos, E. A.; Pessoa, C.; de Moraes, M. O.; Costa-Lotufo, L. V.; Montenegro, R. C.; Ferreira, V. F. Synthesis of new 9-hydroxy-α- and 7-hydroxy-β-pyrannaphthoquinones and cytotoxicity against cancer cell lines. Org. Biomol. Chem.2011, 9, 4315–4322.10.1039/c1ob05209hSearch in Google Scholar PubMed

[13] Shahrisa, A.; Esmati, S.; Miri, R.; Firuzi, O.; Edraki, N.; Nejati, M. Cytotoxic activity assessment, QSAR and docking study of novel bis-carboxamide derivatives of 4-pyrones synthesized by Ugi four-component reaction. Eur. J. Med. Chem.2013, 66, 388–399.10.1016/j.ejmech.2013.05.049Search in Google Scholar PubMed

[14] Hussain, H.; Aziz, S.; Schulz, B.; Krohn, K. Synthesis of a 4H-anthra[1,2-b]pyran derivative and its antimicrobial activity. Nat. Prod. Commun.2011, 6, 841–843.10.1177/1934578X1100600621Search in Google Scholar

[15] Schiller, R.; Tichotová, L.; Pavlík, J.; Buchta, V.; Melichar, B.; Votruba, I.; Kuneš, J.; Špulák, M.; Pour, M. 3,5-Disubstituted pyranone analogues of highly antifungally active furanones: Conversion of biological effect from antifungal to cytostatic. Bioorg. Med. Chem. Lett.2010, 20, 7358–7360.10.1016/j.bmcl.2010.10.052Search in Google Scholar PubMed

[16] Bisht, S. S.; Jaiswal, N.; Sharma, A.; Fatima, S.; Sharma, R.; Rahuja, N.; Srivastava, A.; Bajpai, V.; Kumar, B.; Tripathi, R. P. A convenient synthesis of novel pyranosyl homo-C-nucleosides and their antidiabetic activities. Carbohydr. Res.2011, 346, 1191–1201.10.1016/j.carres.2011.03.006Search in Google Scholar PubMed

[17] Wang, S.; Milne, G.; Yan, X.; Posey, I. J.; Nicklaus, M. C.; Graham, L.; Rice, W. G. Discovery of novel, non-peptide HIV-1 protease inhibitors by pharmacophore searching. J. Med. Chem.1996, 39, 2047–2054.10.1021/jm950874+Search in Google Scholar PubMed

[18] Wang, Y.; Mo, S.-Y.; Wang, S.-J.; Li, S.; Yang, Y.-C.; Shi, J.-G. A unique highly oxygenated pyrano[4,3-c][2]benzopyran-1,6-dione derivative with antioxidant and cytotoxic activities from the fungus phellinusigniarius. Org. Lett.2005, 7, 1675–1678.10.1021/ol0475764Search in Google Scholar PubMed

[19] Shahrisa, A.; Miri, R.; Esmati, S.; Saraei, A.; Mehdipour, A.; Sharifi, M. Synthesis and calcium channel antagonist activity of novel 1,4-dihydropyridine derivatives possessing 4-pyrone moieties. Med. Chem. Res.2012, 21, 284–292.10.1007/s00044-010-9534-8Search in Google Scholar

[20] Osman, S.; Albert, B. J.; Wang, Y.; Li, M.; Czaicki, N. L.; Koide, K. Structural requirements for the antiproliferative activity of pre-mRNA splicing inhibitor FR901464. Chem. Eur. J.2011, 17, 895–904.10.1002/chem.201002402Search in Google Scholar PubMed PubMed Central

[21] Kesten, S. R.; Heffner, T. G.; Johnson, S. J.; Pugsley, T. A.; Wright, J. L.; Wise, L. D. Design, Synthesis, and evaluation of chromen-2-ones as potent and selective human dopamine D4 antagonists. J. Med. Chem.1999, 42, 3718–3725.10.1021/jm990266kSearch in Google Scholar PubMed

[22] Brühlmann, C.; Ooms, F.; Carrupt, P.-A.; Testa, B.; Catto, M.; Leonetti, F.; Altomare, C.; Carotti, A. Coumarins derivatives as dual inhibitors of acetylcholinesterase and monoamine oxidase. J. Med. Chem.2001, 44, 3195–3198.10.1021/jm010894dSearch in Google Scholar PubMed

[23] Banitaba, S. H.; Safari, J.; Baghbanian, S. M.; Rezaei, N.; Tashakkorian, H. Nanozeoliteclinoptilolite as a highly efficient heterogeneous catalyst for the synthesis of various 2-amino-4H-chromene derivatives in aqueous media. Green Chem.2013, 15, 3446–3458.10.1039/c3gc41302kSearch in Google Scholar

[24] Asghari, S.; Baharfar, R.; Alimi, M.; Ahmadipour, M.; Mohseni, M. Synthesis and antibacterial activities of pyrano[3,2-b]pyranones from kojic acid, ethyl cyanoacetate, and benzaldehydes in aqueous K2CO3. Monatsh. Chem.2014, 145, 1337–1342.10.1007/s00706-014-1190-0Search in Google Scholar

[25] Banitaba, S. H.; Safari, J.; Khalili, S. D. Ultrasound promoted one-pot synthesis of 2-amino-4,8-dihydropyrano[3,2-b]pyran-3-carbonitrile scaffolds in aqueous media: a complementary ‘green chemistry’ tool to organic synthesis. Ultrason. Sonochem.2013, 20, 401–407.10.1016/j.ultsonch.2012.07.007Search in Google Scholar PubMed

[26] Kataev, E. A.; Reddy, M. R.; Reddy, G. N.; Reddy, V. H.; Reddy, C. S.; Reddy, B. V. S. Supramolecular catalysis by β-cyclodextrin for the synthesis of kojic acid derivatives in water. New J. Chem.2016, 40, 1693–1697.10.1039/C5NJ01902HSearch in Google Scholar

[27] Asghari, S.; Mohammadnia, M. Synthesis and characterization of pyridine-4-carboxylic acid-functionalized Fe3O4nanoparticles as a magnetic catalyst for the synthesis of tetrahydrobenzo[b]pyran derivatives under solvent-free conditions. Inorg. Nano-Metal. Chem.2017, 47, 1004–1011.10.1080/15533174.2016.1219870Search in Google Scholar

[28] Tabassum, S.; Govindaraju, S.; Pasha, M. A. Ultrasound mediated, iodine catalyzed green synthesis of novel 2-amino-3-cyano-4H-pyran derivatives. Ultrason. Sonochem.2015, 24, 1–7.10.1016/j.ultsonch.2014.12.006Search in Google Scholar PubMed

[29] Liju, W.; Ablajan, K.; Jun, F. Rapid and efficient one-pot synthesis of spiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives catalyzed by l-proline under ultrasound irradiation. Ultrason.Sonochem.2015, 22, 113–118.10.1016/j.ultsonch.2014.05.013Search in Google Scholar PubMed

[30] Teimuri-Mofrad, R.; Mirzaei, F.; Abbasi, H.; Safa, K. D. Synthesis of new binuclear ferrocenyl compounds byhydrosilylation reactions. C. R. Chim.2017, 20, 197–205.10.1016/j.crci.2016.06.011Search in Google Scholar

[31] Teimuri-Mofrad, R.; Gholamhosseini-Nazari, M.; Payami, E.; Esmati, S. Novel ferrocene-based ionic liquid supported on silica nanoparticles as efficient catalyst for synthesis of naphthopyran derivatives. Res. Chem. Intermed.2017, doi: 10.1007/s11164-017-3061-x.10.1007/s11164-017-3061-xSearch in Google Scholar

[32] Teimuri-Mofrad, R.; Gholamhosseini-Nazari, M.; Esmati, S.; Shahrisa, A. A novel tandem Betti/Ullmann oxidation reaction as an efficientroute for synthesis of new oxazepine derivatives. J. Chem. Sci.2017, doi: 10.1007/s12039-017-1343-x.10.1007/s12039-017-1343-xSearch in Google Scholar

[33] Shahrisa, A.; Teimuri-Mofrad, R.; Gholamhosseini-Nazari, M. Chemoselective sequential reactions for the synthesis of 12H-Benzo[a]xanthenes and Dihydro-1H-naphtho[1,2-e][1,3]oxazines. Synlett2015, 26, 1031–1038.10.1055/s-0034-1380323Search in Google Scholar

[34] Shahrisa, A.; Teimuri-Mofrad, R.; Gholamhosseini-Nazari, M. Synthesis of a new class of Betti bases by the Mannich-type reaction: efficient, facile, solvent-free and one-pot protocol. Mol. Divers.2015, 19, 87–101.10.1007/s11030-014-9559-xSearch in Google Scholar PubMed

[35] Teimuri-Mofrad, R.; Shahrisa, A.; Gholamhosseini-Nazari, M.; Arsalani, N. Eco-friendly one-pot, three-component synthesis of novel derivatives of kojic acid by the Mannich-type reaction under solvent-free ball-milling conditions. Res. Chem. Intermed.2016, 42, 3425–3439.10.1007/s11164-015-2221-0Search in Google Scholar

[36] Stöber, W.; Fink, A.; Bohn, E. Controlled growth of monodisperse silica spheres in the micron size range. J. Colloid. Interface. Sci.1968, 26, 62–69.10.1016/0021-9797(68)90272-5Search in Google Scholar

[37] Meng, X. X.; Du, B. X.; Zhao, B.; Li, Y. L.; Chen, C. F. An efficient three-component synthesis of amino-substituted pyrano[3,2-b] pyranones. J. Chem. Res.2013, 37, 638–641.10.3184/174751913X13796142561782Search in Google Scholar

[38] Nishio, K.; Ikeda, M.; Gokon, N.; Tsubouchi, S.; Narimatsu, H.; Mochizuki, Y.; Sakamoto, S.; Sandhu, A.; Abe, M.; Handa, H. Preparation of size-controlled (30–100 nm) magnetite nanoparticles for biomedical applications. J. Magn. Magn. Mater.2007, 310, 2408–2410.10.1016/j.jmmm.2006.10.795Search in Google Scholar

[39] Deng, Y.; Qi, D.; Deng, C.; Zhang, X.; Zhao, D. Superparamagnetic high-magnetization microspheres with an Fe3O4@SiO2 core and perpendicularly aligned mesoporous SiO2 shell for removal of microcystins. J. Am. Chem. Soc.2008, 130, 28–29.10.1021/ja0777584Search in Google Scholar PubMed

Received: 2017-7-6
Accepted: 2017-8-21
Published Online: 2017-11-14
Published in Print: 2017-12-20

©2017 Walter de Gruyter GmbH, Berlin/Boston

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Downloaded on 2.3.2024 from
Scroll to top button