Novel Pumice@SO3H catalyzed efficient synthesis of 2,4,5-triarylimidazoles and acridine-1,8-diones under microwave assisted solvent-free path

https://doi.org/10.1016/j.scp.2021.100485Get rights and content

Highlights

  • Pumice supported sulfonic acid

  • Heterogeneous catalyst

  • Green protocol

  • Microwave assisted synthesis

  • Solvent-free approach

  • Recyclable catalyst

Abstract

In the present investigation, new heterogeneous catalyst pumice supported sulfonic acid (pumice@SO3H) was prepared from natural pumice by simple agitation with chlorosulphonic acid. The catalytic performance of a pumice@SO3H was investigated for the synthesis of 2,4,5-triaryl imidazoles and acridine-1,8-diones under microwave (MW) assisted solvent-free condition. The pumice@SO3H was stable and exhibits a good Brønsted acidic character. The beneficial characteristic features observed with this protocol are the recyclability of catalyst, the solvent free approach, the applicability to a wide variety of substrates, good to excellent yields, and easy to use. The catalyst pumice@SO3H with MW has been increased the green chemistry value of this method.

Introduction

Pumice is a naturally occurring volcanic material which has attracted attention due to various outstanding features associated with it such as high abundance, cheaply available, high porosity, large surface area, light weight and non-toxic nature. The presence of a high percentage of silica and a good number of hydroxyl groups makes it suitable as a backbone to develop new heterogeneous solid acid catalysts. The pumice supported materials have been employed as heterogeneous catalysts in numerous organic transformations (Yuana et al., 2012; Venezia et al., 2001; Alver et al., 2016; Deganello et al., 2000). Due to the presence of huge numbers of hydroxyl groups, Pumice has been converted into several active catalysts such as acidic (Maleki et al., 2020), nano-composites (Valadi et al., 2020), and metal supported catalyst (Liotta et al., 2001; Duca et al., 1995). This volcanic pumice material has also been used as adsorbents (Bekaroglu et al., 2010) and as photo catalysts in the water treatment (Rao et al., 2003).

The microwave assisted reactions is a well established green, and the minimum time consuming path used for the synthesis of a number of N-heterocycles by MCRs. The microwave protocol provides a clean, efficient, quicker, simple and powerful dielectric heating for the construction of complex heterocyclic compounds (Ahankar et al., 2016; Shirole et al., 2017, 2018; Mullassery et al., 2018; Bhatt et al., 2018; Magyar and Hell, 2019; Ulus et al., 2016; Zhu et al., 2017; Alirezvani et al., 2019). The multicomponent reactions (MCRs) have fascinated exceptional protocol for one pot synthesis of diverse heterocyclic compounds. The interesting characteristic features of MCRs are their high atom economy, synthetic efficiency, single operation, and simplicity (Aute et al., 2020; Bienayme et al., 2000; Harikrishna et al., 2020; Naeimi and Didar, 2017; Kiyani and Ghorbani, 2015; Alinezhad et al., 2020; Thwin et al., 2019). The synthesis of 2,4,5-triarylimidazole (Maleki et al., 2015), and acridine-1,8-diones (Yu et al., 2017) are provides the significant illustrations of multicomponent reactions. The imidazole and 1,4-dihydropyridine scaffolds are the important class of heterocyclic compounds, exhibit promising biological and pharmaceutical activities (Gong et al., 2016; Weinstein et al., 2007; Trommenschlager et al., 2017; Takle et al., 2006; Gunduz et al., 2014; Periyasami et al., 2019; Bhosle et al., 2020; Naouri et al., 2020; Joubert and Kapp, 2020; Jamalian et al., 2011) and also found as a core in various natural products (Fig. 1). Some imidazole derivatives are also used in the preparation of ionic liquids which have played a dual role in synthetic organic chemistry as a catalyst as well as solvents (Alinezhad et al., 2017; Nejatianfar et al., 2018; Ngugyen et al., 2019; Shirole and Shelke, 2016).

The imidazole and pyridine based ligands shows a strong coordination capability and resourceful coordination sites (Guo et al., 2013). They display the properties such as luminescence and gas adsorption (Chen et al., 2014; Li et al., 2018), luminescence and magnetic properties (Li et al., 2020), thermal and solid-state fluorescence, anion sensors (Sengar and Narula, 2017), photocatalysis (Zhang et al., 2016) etc.

The various synthetic operations are developed for the synthesis of 2,4,5-triarylimidazole by the three component reaction of aldehydes, benzil and ammonium acetate in the presence of different catalysts includes various nanomaterials, ionic liquids, metal supported catalyst, hybrid catalyst, resins etc. (Alinezhad et al., 2017; Ghasemi et al., 2017; Nejatianfar et al., 2018; Nguyen et al., 2019; Shirole and Shelke, 2016; Arpanahi and Goodajdar, 2020; Mardani et al., 2019; Chakraborty et al., 2017). In addition, many acidic catalysts have been employed for the synthesis of 2,4,5-triarylimidazole such as p-toluene sulphonic acid (Kumar et al., 2012), chitosan−SO3H (Khan and Siddiqui, 2015), mesoporous organosilica supported benzotriazolium ionic liquid (Tan et al., 2020), spherical carbon with SO3H groups (Song et al., 2016), caffeine-H3PO4 (Saghanezhad et al., 2017), citrate trisulfonic acid (Kanaani and Esfahani, 2018), [Et3NH][HSO4] (Deng et al., 2013), (4-SB)T (4-SPh)PHSO4 (Banothu et al., 2017), DES catalyst (Bakavoli et al., 2015), silica sulfuric acid (Shaabani et al., 2006), [Hmim]HSO4 (Khosropour, 2008), oxalic acid (Kokare et al., 2007) and trichloroisocyanuric acid (Hojati et al., 2013), 2-[(1H-imidazole-3-ium-3-yl)methyl]-4-{bis [3-((1H-imidazole-3-ium-3-yl)methyl-(4-hydroxyphenyl]methylene}cyclohexa-2,5-dienone trihydrogen sulfate ([2-(imm)-4-{b (immh)m}c][HSO4]3) (Hilal and Hanoon, 2020), etc.

Also, various synthetic methods have been demonstrated for the synthesis of acridine-1,8-diones by multicomponent reaction in the presence of various catalysts like TEMPO/CuCl2 (Pavithra and Ethiraj, 2020), Fe3O4@SiO2@Ni–Zn–Fe LDH (Gilanizadeh and Zeynizadeh, 2021), graphene-based nanoparticles (Mousavi et al., 2020), glycerol (Tiwari, S.K., 2020), (Fe3O4/HT-SMTU-ZnII) (Zarei and Akhlaghinia, 2017), ultrasound (Chavan, P.N., 2019), nano ferrite (Sunkara et al., 2016), Pd/AlO(OH) (Kilbas et al., 2019), and also various Brønsted acidic catalysts such p-toluenesulfonic acid (Jamalian et al., 2011), silica-bonded S-sulfonic acid (Niknam et al., 2010), [CMIM][CF3COO] (Patil et al., 2014), sulfonic acid-functionalized silica (Ziarani et al., 2014), sulfuric acid-modified poly (vinylpyrrolidone) ((PVP–SO3H)HSO4) (Safaei et al., 2015), etc.

These literatures reported protocol offers several beneficial features, but still some drawbacks such as costly catalyst, lower yields, optimal difficulty etc. With this background and in contribution to our research related to the development of greener methods for the synthesis of valuable heterocyclic scaffolds, we report here a new inexpensive and environmentally benign catalyst pumice@SO3H for the one-pot synthesis of 2,4,5-triarylimidazole and acridine-1,8-dione. The combination of the catalyst pumice@SO3H with MW showed the way to the most effective and efficient methodology with good yield in short period under solvent-free conditions.

Section snippets

Materials and methods

The MW assisted transformation was carried out in the Scientific Microwave (700 W) synthesizer of the RAGA make. Physical constants were taken in an open capillary and are uncorrected. IR spectra were recorded on a PerkinElmer FTIR spectrophotometer. The 1H NMR and 13C NMR spectra were recorded on a Brucker Avance II 500 MHz in CDCl3 using TMS as an internal standard. Mass spectra were recorded on a Finnigan Mass spectrometer. TLC was carried out on pre-coated silica gel aluminum plates to

Result and discussion

The first part of this work was aimed to synthesize pumice@SO3H as a heterogeneous catalyst from naturally occurring non-toxic volcanic pumice stone (Scheme 1). Initially, chlorosulfonic acid was added drop by drop through the dropping funnel into a round bottom flask containing the pumice powder over a period of 50 min. The resulting mixture was stirred well at room temperature for 2 h. Finally, the obtained solid catalyst was washed with the acetone to remove the traces of chlorosulfonic acid

Conclusion

In the present work, we have investigated pumice@SO3H as a novel, cheaper, greener, reusable, solid heterogeneous catalyst. It was successfully used for the synthesis of 2,4,5-triarylimidazoles from aromatic aldehyde, benzil and ammonium acetate as well as for the synthesis of acridine-1,8-diones from aromatic aldehyde, dimedone, and ammonium acetate via multi-component condensation reaction under microwave assisted solvent-free condition with excellent yield in a short time. The significant

Declaration of competing interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgement

We are very much thankful to the Principal, Arts, Science and Commerce College, Rahata, Ahmednagar (India) for providing infrastructural facilities. We are also thankful to SAIF, Punjab University, Chandigarh for providing the good characterization.

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