Titanium dioxide nanowires as green and heterogeneous catalysts for the synthesis of novel pyranocoumarins

Saeed Khodabakhshi; Bahador Karami; Khalil Eskandari; Seyed Jafar Hoseini

doi:10.1016/j.crci.2013.05.005

Titanium dioxide nanowires as green and heterogeneous catalysts for the synthesis of novel pyranocoumarins

Saeed Khodabakhshi ¹ ; Bahador Karami ¹ ; Khalil Eskandari ¹ ; Seyed Jafar Hoseini ¹

¹ Department of Chemistry, Yasouj University, 75918–74831 PO Box 353, Yasouj, Iran

Comptes Rendus. Chimie, Volume 17 (2014) no. 1, pp. 35-40.

Résumé

Titanium dioxide nanowires were employed as novel, recyclable and safe catalysts in a one-pot three-component condensation of aldehydes, malononitrile, and 4-hydroxycoumarin to produce new and known pyrano[2,3-c]chromenes as potent biologically active compounds. A possible catalytic mechanism was also proposed based on the interaction of reactants with TiO₂ nanowires. This expedient new route has advantages, such as the use of a safe and reusable catalyst, simple operation, short reaction times and good to excellent yields.

Supplementary Materials:
Supplementary material for this article is supplied as a separate file:

mmc1.pdf

Métadonnées

Reçu le : 2013-03-04
Accepté le : 2013-05-13
Publié le : 2013-10-24

DOI : 10.1016/j.crci.2013.05.005

Mots-clés : Titanium dioxide, Pyrano[2, 3-c]chromenes, Malononitrile, Nanowires, 4-hydroxycoumarin

Affiliations des auteurs :

Saeed Khodabakhshi ¹ ; Bahador Karami ¹ ; Khalil Eskandari ¹ ; Seyed Jafar Hoseini ¹

¹ Department of Chemistry, Yasouj University, 75918–74831 PO Box 353, Yasouj, Iran

@article{CRCHIM_2014__17_1_35_0,
     author = {Saeed Khodabakhshi and Bahador Karami and Khalil Eskandari and Seyed Jafar Hoseini},
     title = {Titanium dioxide nanowires as green and heterogeneous catalysts for the synthesis of novel pyranocoumarins},
     journal = {Comptes Rendus. Chimie},
     pages = {35--40},
     publisher = {Elsevier},
     volume = {17},
     number = {1},
     year = {2014},
     doi = {10.1016/j.crci.2013.05.005},
     language = {en},
}

TY  - JOUR
AU  - Saeed Khodabakhshi
AU  - Bahador Karami
AU  - Khalil Eskandari
AU  - Seyed Jafar Hoseini
TI  - Titanium dioxide nanowires as green and heterogeneous catalysts for the synthesis of novel pyranocoumarins
JO  - Comptes Rendus. Chimie
PY  - 2014
SP  - 35
EP  - 40
VL  - 17
IS  - 1
PB  - Elsevier
DO  - 10.1016/j.crci.2013.05.005
LA  - en
ID  - CRCHIM_2014__17_1_35_0
ER  -

%0 Journal Article
%A Saeed Khodabakhshi
%A Bahador Karami
%A Khalil Eskandari
%A Seyed Jafar Hoseini
%T Titanium dioxide nanowires as green and heterogeneous catalysts for the synthesis of novel pyranocoumarins
%J Comptes Rendus. Chimie
%D 2014
%P 35-40
%V 17
%N 1
%I Elsevier
%R 10.1016/j.crci.2013.05.005
%G en
%F CRCHIM_2014__17_1_35_0

Saeed Khodabakhshi; Bahador Karami; Khalil Eskandari; Seyed Jafar Hoseini. Titanium dioxide nanowires as green and heterogeneous catalysts for the synthesis of novel pyranocoumarins. Comptes Rendus. Chimie, Volume 17 (2014) no. 1, pp. 35-40. doi : 10.1016/j.crci.2013.05.005. https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2013.05.005/

Version originale du texte intégral

Le texte intégral ci-dessous peut contenir quelques erreurs de conversion par rapport à la version officielle de l'article publié.

1 Introduction

Nowadays, almost all the devices and technologies are becoming smaller and smaller in size, with improved properties. Among the developments, catalytic technology is an important field. Enhancing the contact between the reactants and catalyst was dramatically observed with the use of nanocatalysts, since the nanoscale increases the exposed surface area of the active component of the catalyst [1–3]. Among nanomaterials, titanium dioxide (TiO₂) is a biocompatible and environmentally benign catalyst. TiO₂ nanomaterials, including nanoparticles, nanorods, nanowires, and nanotubes, are widely investigated for various applications in photocatalysis, photovoltaics, batteries, smart surface coatings, photonic crystals, sensors, ultraviolet blockers, pigment, and paints [4]. Synthetically, multi-component reactions (MCRs) have emerged as useful methods because the combination of three components to generate new products in a single step is extremely economical [5]. Besides, in medicine, pyranocoumarins are well recognized due to their importance in biological and pharmaceutical researches [6]. Several methods have been reported for the synthesis of pyrano[2,3-c]coumarin as biologically active compounds. In general, pyrano[2,3-c]coumarin derivatives are accessible via the one-pot three-component reaction of hydroxycoumarins, carbonyl compounds and active methylenes in the presence of basic catalysts [7] In recent studies, the synthesis of pyrano[2,3-c]chromenes via a three-component reaction has been described using various reagents, such as sodium dodecyl sulfate (SDS) [8], H₆P₂W₁₈O₆₂·18H₂O [9], hexamethylenetetramine [10] magnesium oxide (MgO) [11], diammonium hydrogen phosphate (DAHP), (S)-proline [12], KF–Al₂O₃ [13], tetrabutylammonium bromide (TBAB) [14], and triethylbenzylammonium chloride (TEBA) [15]. However, some of these mentioned reports suffer from drawbacks, such as long reaction times, low product yields, harsh reaction conditions, and the use of excessive amounts of catalyst. In this work, a new methodology to obtain novel and known pyrano[2,3-c]chromene under ultrasound irradiation, via a one-pot three-component condensation, is reported. In this paper, we introduce a new application of titanium dioxide nanowires as a novel and safe catalyst for the synthesis of novel and known pyranocoumarin derivatives.

2 Experimental

2.1 General procedure for preparation of TiO₂ nanowires

In a typical synthesis, 0.115 g of commercial Degussa P25 powder was mixed with 3.5 mL of 10 M NaOH and 3.5 mL of ethanol. The mixed solution was then transferred into a 35 mL Teflon-lined stainless-steel autoclave. The autoclave was maintained at 180 °C under autogenous pressure for 24 h and then cooled to room temperature naturally. The sample so obtained was filtered off, washed several times with a dilute HCl aqueous solution and water until the pH value of the washing solution was about 7. The TiO₂ nanowires so obtained have diameters in the 60–150 nm range and are a few microns in length [16,17].

2.2 General procedure for the synthesis of pyrano[2,3-c]coumarin

Malononitrile (1) (1.1 mmol), aromatic aldehyde 2 (1 mmol), 4-hydroxycoumarin (3) (1 mmol), and TiO₂ NWs (0.03 mmol) were added to a 10-mL mixture EtOH/H₂O (50/50) in a 25-mL pyrex flask and refluxed for an appropriate time (Table 2). The reaction progress was controlled by thin layer chromatography (TLC) using hexane/EtOAc (1:1). After completion of the reaction, the solvent was removed under vacuum, the crude products 4 were obtained after recrystalization from EtOH.

Entry	Product	Time (min)	Yield^a (%)	Mp. (°C) [lit.]
4a		60	90	261–263 [10]
4b		45	85	246–248 [10]
4c		60	92	270–272 [10]
4d		45	90	263–265 [10]
4e		40	90	260–262 [10]
4f		65	95	255–257 [10]
4g		60	95	262–264 [10]
4h		70	85	260–262 [10]
4i		45	95	276–278 [24]
4j		60	90	290–292^b
4k		55	85	270–272^b
4l		70	80	262–264 [14]

^a Isolated yields.

^b Novel compounds.

2.3 Spectral data of some compounds

2.3.1 Compound (4i)

IR (KBr): 3396, 3321, 3195, 2202, 1706, 1671, 1607, 1381, 1053 cm⁻¹. ¹H NMR (DMSO, 400 MHz): δ 7.90 (dd, 1H, J = 7.8, 1.2 Hz), 7.75–7.70 (m, 1H), 7.52–7.43 (m, 6H), 7.30–7.28 (m, 2H), 4.50 (s, 1H) ppm. ¹³C NMR (DMSO, 100 MHz): δ 159.55, 157.94, 153.70, 152.18, 146.02, 132.99, 130.69, 130.39, 130.05, 126.94, 124.65, 122.54, 121.68, 119.05, 116.57, 112.98, 103.15, 57.31, 36.59. Anal. Calcd. for C₁₉H₁₁BrN₂O₃: C, 57.74; H, 2.81; N, 7.09%. Found: C, 58.05; H, 2.68; N, 7.16%.

2.3.2 Compound (4j)

IR (KBr): 3408, 3280, 3175, 2203, 1705, 1674, 1602, 1381, 1055 cm⁻¹. ¹H NMR (DMSO, 400 MHz): δ 7.90 (dd, 1H, J = 7.8, 1.2 Hz), 7.76–7.72 (m, 1H), 7.55–7.48 (m, 4H), 7.55–7.19 (m, 3H), 5.19 (d, 1H, J = 1.6 Hz). ¹³C NMR (DMSO, 100 MHz): δ 159.38, 158.77, 152.11, 133.18, 133.09, 129.93, 129.83, 124.84, 124.70, 124.66, 122.29, 118.73, 116.68, 115.25, 112.56, 38.83 ppm. Anal. Calcd. for C₁₉H₁₀ClFN₂O₃: C, 61.89; H, 2.73; N, 7.60%. Found: C, 61.90; H, 2.55; N, 7.72%.

2.3.3 Compound (4k)

IR (KBr): 3391, 3180, 2196, 1712, 1674, 1608, 1381, 1240, 1054 cm⁻¹. ¹H NMR (DMSO, 400 MHz): δ 7.90 (dd, 1H, J = 8.0 Hz), 7.73–7.69 (m, 1H), 7.44–7.38 (m, 7H), 7.18 (d, 2H, J = 8.8 Hz), 6.95 (d, 2H, J = 8.8 Hz), 5.06 (s, 2H), 4.40 (s, 1H). ¹³C NMR (DMSO, 100 MHz): δ 159.51, 157.87, 157.45, 153.09, 152.06, 137.05, 135.60, 132.83, 128.76, 128.40, 127.79, 127.64, 124.63, 122.41, 119.30, 116.53, 114.61, 112.97, 104.19, 69.17, 58.09, 36.13. Anal. Calcd. for C₂₆H₁₈N₂O₄: C, 73.92; H, 4.29; N, 6.63%. Found: C, 74.15; H, 4.15; N, 6.79%.

2.3.4 Compound (4l)

IR (KBr): 3340, 3312, 2188, 1697, 1669, 1598, 1379, 1066 cm⁻¹. ¹H NMR (DMSO, 400 MHz): δ 8.44(d, 1H, J = 6.4 Hz), 7.96 (d, 2H, J = 8.0 Hz), 7.83 (d, 1H, J = 8.0 Hz), 7.76–7.33 (m, 8H), 5.48 (s, 1H). ¹³C NMR (DMSO, 100 MHz): δ 159.55, 157.83, 153.80, 152.07, 133.26, 132.93, 130.93, 128.47, 127.43, 126.10, 126.00, 125.85, 125.75, 124.74, 123.43, 122.43, 119.15, 116.61, 112.96, 104.65, 58.49 ppm. Anal. Calcd. for C₂₃H₁₄N₂O₃: C, 75.40; H, 3.85; N, 7.65%. Found: C, 75.65; H, 3.70; N, 7.53%.

3 Results and discussion

In continuation of our efforts toward the development of novel, efficient, and green procedures for the synthesis of organic compounds [18–20] using safe catalysts [21–23], we turned our attention toward the three-component condensation of malononitrile (1), aromatic aldehydes 2, and 4-hydroxycoumarin (3) to produce pyrano[2,3-c]coumarins 4 in the presence of TiO₂ nanowires (Scheme 1).

Scheme 1
Synthesis of pyrano[2,3-c]coumarins using TiO₂ NWs.

The scanning electron microscope (SEM) image of TiO₂ nanowires is shown in Fig. 1. In order to optimize the reaction conditions, we used both protic and aprotic solvents in the presence of various amounts of the TiO₂ NWs in the reaction of benzaldehyde, 1 and 3 as a model to investigate the effects of the solvent and the catalyst for preparing compounds 4a. In this case, the substrates were mixed together in 10 mL of the solvent.

As shown in Table 1, we found that polar and protic solvents, such as H₂O and EtOH or MeOH, afford better yields than aprotic ones and also an equal mixture of H₂O and EtOH is the most effective solvent. The effect of temperature was also studied for this reaction and it was found that the reaction would be completed after 180 min at room temperature. However, the thermal-assisted model reaction is efficiently carried out by adding catalytic amounts of TiO₂ NWs (3 mol%) in a mixture of EtOH and H₂O (50/50).

Entry	Catalyst (mol%)	Solvent	Yield (%)
1	5	CH₂Cl₂	50
2	5	CH₃Cl	50
3	5	EtOH	85
4	5	MeOH	85
5	5	H₂O	65
6	–	H₂O/EtOH	Trace
7	1	H₂O/EtOH	50
8	3	H₂O/EtOH	90
9	5	H₂O/EtOH	90
10	10	H₂O/EtOH	85

After optimization of the reaction conditions, in order to extend the scope of this reaction, a wide range of aromatic aldehydes were used with 1 and 3 (Table 2). All the products were characterized by comparison of their spectra and physical data with those reported in the literature [10,14,24].

Table 3 demonstrates the merit of this method for the synthesis of pyrano[2,3-c]coumarins in comparison with previously reported results. As it can be seen from Table 3, piperidine was employed as a basic catalyst under refluxing EtOH, but this method could not afford good yields (entry 1). In the case of (S)-proline (entry 4), the product was obtained in low yield in a long time. In other variations, such as DAHP (entry 3), KF–Al₂O₃ (entry 5), and TEBA (entry 6), the methods need too long reaction times. We believe that these reactions can be efficiently carried out under our suggested conditions with respect to reaction times and product yield.

Entry	Conditions	Time (min)	Yield (%)
1	Piperidine (0.5 mL), EtOH, reflux	30	70 [7]
2	SDS (20 mol%), H₂O, 60 °C	120	85 [8]
3	DAHP (10 mol%), H₂O:EtOH (1:1), room temperature	180	81 [12]
4	(S)-Proline (10 mol%), H₂O:EtOH (1:1), reflux	240	72 [12]
5	KF–Al₂O₃ (0.125 g), EtOH, reflux	240	90 [13]
6	TEBA (0.07 g), H₂O, 90 °C	420	96 [15]
7	TiO₂NWs (3 mol%), H₂O:EtOH (1:1), reflux	60	90^b

^a Synthesis of 4a.

^b Present work.

A mechanistic rationale for the formation of pyranocoumarins 4 is suggested in Scheme 2. It seems that the reaction takes place in three steps. It is reasonable to assume that the initial event involves the generation of the arylmethylene via a Knoevenagel condensation of the aldehyde and malononitrile catalyzed by TiO₂ NWs. In the next steps, a Michael-type addition to the arylmethylene and subsequent heterocyclization promoted by TiO₂ NWs gives the corresponding products 4.

Scheme 2
A plausible mechanism for the formation of pyranocoumarins 4 catalyzed by TiO₂ NWs.

The main disadvantage of many reported methods for these reactions is that the catalysts are destroyed in the work-up procedure and cannot be recovered or reused. In these processes, as outlined in Fig. 2, the TiO₂ NWs showed recyclability up to four cycles, during which there are a little losses in the catalytic activity.

Fig. 2
Recyclability of TiO₂ NWs for synthesis of 4a. Reaction time: 60 min.

4 Conclusion

In summary, a new application of titanium dioxide nanowires as an efficient and heterogeneous catalyst in the reaction between 4-hydroxycoumarin, various aromatic aldehydes and malononitrile to produce pyrano[2,3-c]chromens of potential synthetic and pharmaceutical interest was presented. This method has unique merits, such as the use of a small amount of a safe catalyst, high product yields, short reaction times, and simple operation and work-up procedure, which make it a valid contribution to the existing methodologies.

Acknowledgements

The authors gratefully acknowledge Yasouj University of Iran for supporting this work.

Bibliographie

[1] V. Polshettiwar; R.S. Varma Green Chem., 12 (2010), pp. 743-754

[2] B. Karami; S.J. Hoseini; K. Eskandari; A. Ghasemi; H. Nasrabadi Catal. Sci. Technol., 2 (2012), pp. 331-338

[3] M.A. Rezvani; A.F. Shojaie; M.H. Loghmani Catal. Commun., 25 (2012), pp. 36-40

[4] M. Hosseini-Sarvari; E. Safary; A. Jarrahpour; R. Heiran; S. Chaturvedi; P.N. Dave; N.K. Shah J. Saudi Chem. Soc., 16 (2013), pp. 73-79

[5] B. Karami; S. Khodabakhshi; K. Eskandari Tetrahedron Lett., 53 (2012), pp. 1445-1446

[6] A. Shaabani; A. Rahmati; A.H. Rezayan; H.R. Khavasi J. Iran Chem. Soc., 8 (2001), p. 24

[7] N.A. Greenwood; N. Earnshaw Chemistry of the Elements, Pergamon, Oxford, 1984 (ISBN: 0-08-022057-6)

[8] H. Mehrabi; H. Abusaidi J. Iran. Chem. Soc., 78 (2010), pp. 90-894

[9] M.M. Heravi; B.A. Jani; F. Derikvand; F.F. Bamoharram; H.A. Oskooie Catal. Commun., 10 (2008), pp. 272-275

[10] H.J. Wang; J. Lu; Z.H. Zhang Monatsh. Chem., 141 (2010), pp. 1107-1112

[11] M. Seifi; H. Sheibani Catal. Lett., 126 (2008), pp. 275-279

[12] S. Abdolmohammadi; S. Balalaie Tetrahedron Lett., 48 (2007), pp. 3299-3303

[13] W. Xiang-Shan; Z. Zhao-Sen; S. Da-Qing; W. Xian-Yong; Z. Zhi-Min Chin. J. Org. Chem., 25 (2005), pp. 1138-1141

[14] J.M. Khurana; S. Kumar Tetrahedron Lett., 50 (2009), pp. 4125-4127

[15] S. Da-Qing; W. Jing; Z. Qi-Ya; W. Xiang-Shan Chin. J. Org. Chem., 26 (2006), pp. 643-647

[16] A. Gomathi; S.J. Hoseini; C.N.R. Rao J. Mater. Chem., 19 (2009), pp. 988-995

[17] B.M. Wen; C.Y. Liu; Y. Liu New J. Chem., 29 (2005), p. 969

[18] B. Karami; K. Eskandari; S. Khodabakhshi Arkivoc, ix (2012), pp. 76-84

[19] B. Karami; M. Farahi; S. Khodabakhshi Helv. Chim. Acta, 95 (2012), pp. 455-460

[20] B. Karami; S. Khodabakhshi; M. Nikrooz Polycyclic Aromat. Compd., 31 (2011), pp. 97-109

[21] S. Khodabakhshi; B. Karami Catal. Sci. Technol., 2 (2012), pp. 1940-1944

[22] B. Karami; V. Ghashghaee; S. Khodabakhshi Catal. Commun., 20 (2012), pp. 71-75

[23] B. Karami; M. Taei; S. Khodabakhshi; M. Jamshidi J. Sulfur Chem., 33 (2012), pp. 331-338

[24] A. Patra; T. Mahapatra J. Ind. Chem. Soc., 89 (2012), pp. 925-932

Cité par

Behrooz Maleki; Ali Jamshidi; Sahar Peiman; Mohammad Reza Housaindokht Tri-vanadium Substituted Dawson-type Heteropolytungstate Nanocomposite (g-C 3 N 4 /Fe 3 O 4 @P 2 W 15 V 3 ) as a Novel, Green, and Recyclable Nanomagnetic Catalyst in the Synthesis of Tetrahydrobenzo[b]Pyrans, Polycyclic Aromatic Compounds, Volume 44 (2024) no. 2, p. 994 | DOI:10.1080/10406638.2023.2184398
Niloofar Haghdadi; Sakineh Asghari; Ghasem Firouzzadeh Pasha Synthesis and characterization of functionalized nano NaY zeolite with metformin and use for the synthesis of 2-amino-4H-chromenes, Research on Chemical Intermediates, Volume 50 (2024) no. 5, p. 1961 | DOI:10.1007/s11164-024-05258-w
Jayalakshmi M; Francis Joy; Aatika Nizam; Suresh Babu Naidu Krishna Multicomponent Synthesis Strategies, Catalytic Activities, and Potential Therapeutic Applications of Pyranocoumarins: A Comprehensive Review, Chemistry Biodiversity, Volume 20 (2023) no. 10 | DOI:10.1002/cbdv.202300836
Pooja Garg; Sabbasani Rajasekhara Reddy Biomass‐derived Sugar Ionic Liquid as a Sustainable Organocatalyst: An Efficient Synthesis of Functionalized Dihydropyrano Coumarins, Asian Journal of Organic Chemistry, Volume 11 (2022) no. 9 | DOI:10.1002/ajoc.202200322
Giovanna Bosica; Roderick Abdilla Recent Advances in Multicomponent Reactions Catalysed under Operationally Heterogeneous Conditions, Catalysts, Volume 12 (2022) no. 7, p. 725 | DOI:10.3390/catal12070725
Bubun Banerjee; Manmeet Kaur; Aditi Sharma; Arvind Singh; Anu Priya; Vivek Kumar Gupta; Vikas Jaitak Glycine Catalyzed One-Pot Three-Component Synthesis of Structurally Diverse 2-Amino Substituted Pyran Annulated Heterocycles in Aqueous Ethanol under Refluxed Conditions, Current Green Chemistry, Volume 9 (2022) no. 3, p. 162 | DOI:10.2174/2213346110666221212152202
T. A. J. Siddiqui; Shoyebmohamad F. Shaikh; Balaji B. Totawar; Madhuri Dumpala; Mohd Ubaidullah; Badr M. Thamer; Rajaram S. Mane; Abdullah M. Al-Enizi Tungsten oxides: green and sustainable heterogeneous nanocatalysts for the synthesis of bioactive heterocyclic compounds, Dalton Transactions, Volume 50 (2021) no. 6, p. 2032 | DOI:10.1039/d0dt04238b
U. P. Patil; Rupesh C. Patil; Suresh S. Patil Biowaste-Derived Heterogeneous Catalyst for the One-Pot Multicomponent Synthesis of Diverse and Densely Functionalized 2-Amino-4H-Chromenes, Organic Preparations and Procedures International, Volume 53 (2021) no. 2, p. 190 | DOI:10.1080/00304948.2020.1871309
Maedeh Saeedi Mirak-Mahaleh; Kurosh Rad-Moghadam A novel amphipathic low-melting complex salt: An efficient homogeneous catalyst for synthesis of pyran-annulated heterocyclic scaffolds and pyrido[2,3-d]pyrimidines, Journal of Molecular Liquids, Volume 307 (2020), p. 112989 | DOI:10.1016/j.molliq.2020.112989
Mehrnoush Tamimi; Majid M. Heravi; Masoud Mirzaei; Vahideh Zadsirjan; Nahid Lotfian; Hossein Eshtiagh‐Hosseini Ag3[PMo12O40]: An efficient and green catalyst for the synthesis of highly functionalized pyran‐annulated heterocycles via multicomponent reaction, Applied Organometallic Chemistry, Volume 33 (2019) no. 9 | DOI:10.1002/aoc.5043
Moaz M. Abdou; Rasha A. El-Saeed; Samir Bondock Recent advances in 4-hydroxycoumarin chemistry. Part 2: Scaffolds for heterocycle molecular diversity, Arabian Journal of Chemistry, Volume 12 (2019) no. 7, p. 974 | DOI:10.1016/j.arabjc.2015.06.029
Nader Daneshvar; Omid Goli‐Jolodar; Reyhaneh Karimi‐Chayjani; Mohaddeseh Safarpoor Nikoo Langarudi; Farhad Shirini Sustainable and Eco‐Friendly Method for the Synthesis of Some Bioactive Derivatives of Biscoumarin and Pyrano[3,2‐c]Chromene‐3‐Carbonitrile Using Taurine, as the Catalyst, ChemistrySelect, Volume 4 (2019) no. 5, p. 1562 | DOI:10.1002/slct.201803210
Hamideh Mohamadi Tanuraghaj; Mahnaz Farahi A novel protocol for the synthesis of pyrano[2,3-h]coumarins in the presence of Fe3O4@SiO2@(CH2)3OCO2Na as a magnetically heterogeneous catalyst, New Journal of Chemistry, Volume 43 (2019) no. 12, p. 4823 | DOI:10.1039/c8nj06415f
Saeed Khodabakhshi; Bahareh Abdol Pour Mori; Mojtaba Baghernejad; Sajad Kiani A Green One-Pot Synthesis of New and Known 5-Oxatetracene Derivatives Using Carboxylated Multiwall Carbon Nanotubes, Polycyclic Aromatic Compounds, Volume 39 (2019) no. 5, p. 434 | DOI:10.1080/10406638.2017.1340315
Mina Jafari Nasab; Ali Reza Kiasat; Raziyeh Zarasvandi β-Cyclodextrin nanosponge polymer: a basic and eco-friendly heterogeneous catalyst for the one-pot four-component synthesis of pyranopyrazole derivatives under solvent-free conditions, Reaction Kinetics, Mechanisms and Catalysis, Volume 124 (2018) no. 2, p. 767 | DOI:10.1007/s11144-018-1373-5
Mozhgan Shahamirian; Sajad Kiani; Abbas Jorsaraei Talar; Saeed Khodabakhshi Functionalized Nano Graphene Platelets as Green Catalyst to Synthesize New and Known Benzoyl-1,4-diazanaphthalene and Study of Their Local Aromaticity, Polycyclic Aromatic Compounds, Volume 37 (2017) no. 1, p. 81 | DOI:10.1080/10406638.2015.1099552
Mahnaz Farahi; Bahador Karami; Raziyeh Keshavarz; Foroogh Khosravian Nano-Fe3O4@SiO2-supported boron sulfonic acid as a novel magnetically heterogeneous catalyst for the synthesis of pyrano coumarins, RSC Adv., Volume 7 (2017) no. 74, p. 46644 | DOI:10.1039/c7ra08253c
Marwa Gardelly; Belsem Trimech; Mohamed Amine Belkacem; Mounira Harbach; Soukaina Abdelwahed; Amor Mosbah; Jalloul Bouajila; Hichem Ben Jannet Synthesis of novel diazaphosphinanes coumarin derivatives with promoted cytotoxic and anti-tyrosinase activities, Bioorganic Medicinal Chemistry Letters, Volume 26 (2016) no. 10, p. 2450 | DOI:10.1016/j.bmcl.2016.03.108
Saeed Khodabakhshi; Alimorad Rashidi; Ziba Tavakoli; Mojtaba Baghernejad; Amir Yadegari The first catalytic application of oxidized carbon nanotubes in a four-component synthesis of fused heterocycles, Monatshefte für Chemie - Chemical Monthly, Volume 147 (2016) no. 4, p. 791 | DOI:10.1007/s00706-015-1532-6
Bahador Karami; Mahtab Kiani Silica-supported molybdic acid: preparation, characterization, and its catalytic application in synthesis of pyranocoumarins, Monatshefte für Chemie - Chemical Monthly, Volume 147 (2016) no. 6, p. 1117 | DOI:10.1007/s00706-015-1551-3
Mojtaba Baghernejad; Saeed Khodabakhshi; Sanaz Tajik Isatin-based three-component synthesis of new spirooxindoles using magnetic nano-sized copper ferrite, New Journal of Chemistry, Volume 40 (2016) no. 3, p. 2704 | DOI:10.1039/c5nj03027g
Bahador Karami; Mahtab Kiani Novel silica-supported molybdic acid (SSMA): an efficient catalyst for the synthesis of new azo dyes, Research on Chemical Intermediates, Volume 42 (2016) no. 4, p. 3373 | DOI:10.1007/s11164-015-2218-8
Yinglei Wang; Hongyong Ye; Guangling Zuo; Jun Luo Synthesis of a novel poly (ethylene glycol) grafted N,N-dimethylaminopyridine functionalized dicationic ionic liquid and its application in one-pot synthesis of 3,4-dihydropyrano[3,2-c]chromene derivatives in water, Journal of Molecular Liquids, Volume 212 (2015), p. 418 | DOI:10.1016/j.molliq.2015.09.030
Saeed Khodabakhshi; Masoud Khaleghi Abbasabadi; Mojtaba Baghrnejad; Farzaneh Marahel A Green Strategy to Prepare Warfarin‐like Compounds Catalyzed by Zirconium Oxychloride, Journal of the Chinese Chemical Society, Volume 62 (2015) no. 1, p. 9 | DOI:10.1002/jccs.201400266
Bahador Karami; Mahtab Kiani; S. Jafar Hosseini; Mehrangiz Bahrami Synthesis and characterization of novel nanosilica molybdic acid and its first catalytic application in the synthesis of new and known pyranocoumarins, New Journal of Chemistry, Volume 39 (2015) no. 11, p. 8576 | DOI:10.1039/c5nj01302j
Ardeshir Khazaei; Mohammad Ali Zolfigol; Fatemeh Karimitabar; Iraj Nikokar; Ahmad Reza Moosavi-Zare N,2-Dibromo-6-chloro-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide 1,1-dioxide: an efficient and homogeneous catalyst for one-pot synthesis of 4H-pyran, pyranopyrazole and pyrazolo[1,2-b]phthalazine derivatives under aqueous media, RSC Advances, Volume 5 (2015) no. 87, p. 71402 | DOI:10.1039/c5ra10730j
Saeed Khodabakhshi; Bahador Karami; Khalil Eskandari Molybdate sulfuric acid-catalyzed one-pot synthesis of substituted coumarins under solvent-free conditions, Research on Chemical Intermediates, Volume 41 (2015) no. 10, p. 7263 | DOI:10.1007/s11164-014-1810-7
Saeed Khodabakhshi; Mozhgan Shahamirian; Mojtaba Baghernejad Solvent-free and One-pot Synthesis of Trisubstituted Methanes Containing Coumarin Catalysed by Yttrium(III) Nitrate, Journal of Chemical Research, Volume 38 (2014) no. 11, p. 655 | DOI:10.3184/174751914x14137247130017
Saeed Khodabakhshi; Mozhgan Shahamirian; Mojtaba Baghernejad A New Three-Component Coupling reaction of Aryl Glyoxal, Malononitrile, and 4-Hydroxy Coumarin Catalysed by Recyclable Tio2 nanoparticles, Journal of Chemical Research, Volume 38 (2014) no. 8, p. 473 | DOI:10.3184/174751914x14050999895192
Saeed Khodabakhshi; Bahador Karami; Mojtaba Baghernejad Iron(II,III) oxide nanoparticle-catalyzed selective synthesis of unknown dihydropyrano[c]chromenes under green conditions, Monatshefte für Chemie - Chemical Monthly, Volume 145 (2014) no. 11, p. 1839 | DOI:10.1007/s00706-014-1240-7
Saeed Khodabakhshi; Bahador Karami Graphene oxide nanosheets as metal-free catalysts in the three-component reactions based on aryl glyoxals to generate novel pyranocoumarins, New J. Chem., Volume 38 (2014) no. 8, p. 3586 | DOI:10.1039/c4nj00228h
Fariba Jafari; Saeed Kodabakhshi; Sanaz Gharehzadeh Shirazi Zinc oxide nanorods: a new application as a powerful catalyst for the green one-pot synthesis of new warfarin analogs, RSC Adv., Volume 4 (2014) no. 89, p. 48095 | DOI:10.1039/c4ra06669c
Saeed Khodabakhshi; Bahador Karami Tungstate sulfuric acid catalyzed one-pot synthesis of a new class of aroylamido coumarins under solvent-free conditions, Tetrahedron Letters, Volume 55 (2014) no. 51, p. 7136 | DOI:10.1016/j.tetlet.2014.11.016

Cité par 33 documents. Sources : Crossref

Commentaires - Politique

Il n'y a aucun commentaire pour cet article. Soyez le premier à écrire un commentaire !

Publier un nouveau commentaire:

Publier une nouvelle réponse: