Document Type : Original Article

Authors

1 Department of Chemistry, Amruteshwar ACS, College, Vinzar, Pune (MS) India-412213

2 Department of Chemistry, D.Y. Patil ACS, College, affiliated; Savitribai Phule Pune University, Pimpri, Pune (MS) India-411018

3 Department of Chemistry, DD Bhoyar College, Mouda, Nagpur (MS) India-441104

4 Department of Chemistry, Vidnyan Mahavidhyalaya, Sangola, Solapur (MS) India 413307

5 Department of Chemistry, PDVP College, Tasgaon, Sangali (MS) India 416312

6 School of Chemical Sciences, SRTM University, Nanded (MS) India 431606

Abstract

An efficient and convenient method has been developed for the synthesis of 2-amino-5-oxo-4-phenyl-4, 5-dihydropyrano[3,2-c]chromene-3-carbonitrile derivatives from one-pot multicomponent reaction between 4-hydroxy-2H-chromen-2-one, aromatic aldehydes and malononitrile catalyzed by DTP/SiO2 as an efficient and reusable heterogeneous catalyst. The current method provides adavtages over reported method viz simple operational procedure, easy isolation and recyclability of the catalyst, environmental benign, reduced reaction time and superior yield.

Graphical Abstract

DTP/SiO2:An Efficient And Reusable Heterogeneous Catalyst For synthesis of dihydropyrano[3,2-c]chromene-3-carbonitrile derivatives

Keywords

Main Subjects

Introduction

Silica-supported DTP/SiO2 is simple to prepare and shows good acidic characteristics. The acidic properties of DTP/SiO2 can be controlled by activation temperature and has shown significant catalytic activity [1]. DTP/SiO2 exhibits efficient heterogeneous catalytic properties for the synthesis of wide variety important organic building blocks such as α-aminophosphonate [2]. Moreover, it is successfully employed as catalyst for the many organic transformations viz C-H activation and functionalization of nitrogen containing aromatic heterocycles [3, 4], Fries rearrangement [5], Friedel-Crafts benzylation of anisole [6].

The pyrans are considered as an important building block for the synthesis of several natural products [7] and photochromic materials [8]. The heterocyclic entities containing pyrans ring show many medicinal and pharmacological properties and are involved in may biochemical reactions [8]. Furthermore, pyrans serve as important synthetic intermediates for the synthesis of biologically important compounds such as pyrano-pyridnes [9], poly-azanaphthalenes [10], pyrano[2-c]pyrimidines [11], and pyridin-2-ones [12]. Hence, the synthesis of hetrocyclic compounds containing pyran nucleus has attracted the attention of many synthetic and medicinal chemist. Moreover, the herteocyclic compounds containing pyrano[3,2-c]chromene nucleus is a class of important heterocycle with broad spectrum of biological activities [13] involving spasmolytic, diuretic, anti-coagulant, anti-cancer and anti-anaphylactic activity [14]. The chromene building block with fused ring system has proved to expand the biological spectrum with superior anti-bacterial profile against numerous microbes such as bacteria and fungi [15]. The fused chromene containing heterocycles has shown the excellent biological properties viz antiproliferative [16], sexpheromonal [17], mutagenicitical [18], anti-tumor [19], anti-viral [20]and CNS depressant activities [21].

There are many methods available in the literature for the synthesis of dihydropyrano[3,2-c]chromene compounds via one-pot multicomponent reaction (MCR) between 4-hydroxycoumarin with aldehydes and malononitriles such as H6P2W18O62/18H2O [22], sodium dodecyl sulfate (SDS) [23], DBU  [24], Tetrabutylammonium bromide (TBAB) under solvent free and in aqueous condition [25], ionic liquid [26], sulfonic acid functionalized silica (SiO2PrSO3H) [27], poly(N,N'-dibromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS] and N,N,N',N'-tetrabromobenzene-1,3-disulfonamide [TBBDA] [28], trisodium citrate [29], Biguanide-functionalized Fe3O4/SiO2 magnetic nanoparticles [30], inorganic–organic hybrid magnetic nanocatalyst Fe2O3 [31] Ru(II) phosphine complexes [32], Silica-bonded n-propylpiperazine sodium n-propionate [33],  2-hydroxyethylammonium formate (ionic liquid) [34], bleaching earth clay [35] etc. However, these reported methods have been found to be inadequate in terms of longer reaction time, lower practical yields, ease of handling of hazardous chemicals, isolation of the product, lack of catalytic reusability etc. Taking into account the limitation of the reported methods, we can still have a scope to develop new method for the synthesis of dihydropyrano[3,2-c]chromene derivatives. To address the shortcomings of reported methods, herein we reported DTP/SiO2 as efficient, recyclable heterogeneous catalysts for the synthesis of dihydropyrano[3,2-c]chromene derivatives.

Experimental

General

All the physical constants were recorded in an open capillary tube and were uncorrected. The reagents, chemicals and solvents used were of synthetic grades and were used as obtained. The reactions were monitored by thin layer chromatography on precoated sheets of alumina gel-G (Merk, Germany) using iodine vapours and or UV light for detection. The Infra-Red (IR) spectra were recorded on Schimadzu Spectrophotometer (KBr pellets). 1H NMR (300MHz) and 13C NMR (100 MHz) spectra were recorded in DMSO-d6 or CDCl3 using TMS an internal standard with an Avance spectrometer (Bruker, Germany). Mass spectra were determined on an EI-Schimadzu QP 2010+ GCMS system.

2.1. General procedure for the synthesis of 2-amino-5-oxo-4-phenyl-4,5-dihydropyrano[3,2-c]chromene-3-carbonitrile derivatives 4:

A mixture of 4-hydroxy-2H-chromen-2-one 1 (1 mol), aldehyde (2a–2n) (1.1 mol), malononitrile 3 (1.1 mmol), and DTP/SiO2 (20 wt %) in DMF (10 mL) was heated to 60°C with stirring about 30-50 Minute (Table 2). The progress of reaction was checked by TLC. After completing the conversion of reactant into product (by TLC), the catalyst was filtered off and reaction mixture was allowed to cool at room temperature. To this cooled mixture, ice cold water (50 mL) was added and stirred mechanically for 5-10 min. The solid was separated out, filtered and recrystallized from ethanol to afford the pure products 4 a-n.

2.1.1.Product 4a: Pale yellow powder; (purified by recrystallization with ethanol); IR (KBr) cm-1: 3323, 3204, 2195, 1720, 1668, 1601, 1519, 1381, 1264, 1143, 1048, 761, 481; 1H NMR (300 MHz, DMSO-d6 TMS) δ ppm; 4.40 (1H, s, pyran-CH), 7.21-7.30 (5H, m, arom.), 7.36 (2H, s, NH2), 7.40-7.48 (2H, m, arom.), 7.69 (1H, t, J = 7.2 Hz, arom.), 7.86 (1H, d,  J = 7.2 Hz, arom); 13C NMR (100 MHz, DMSO-d6, TMS) δ ppm; 37.1, 57.9, 103.8, 112.9, 116.6, 119.2,122.5, 124.7, 127.2, 127.7, 128.6, 133.0, 143.4, 152.2, 153.5, 158.1, 159.6.

2.1.2. Product 4b: Grayish solid; (purified by recrystallization with ethanol); IR (KBr) cm-1: 3319, 3310, 3195, 2196, 1718, 1676, 1608, 1377, 1057, 954, 757, 506; 1H NMR (300 MHz, DMSO-d6 TMS) δ ppm; 2.21 (3H, s, CH3), 4.36 (1H, s, CH), 7.05-7.11 (4H, m, arom.), 7.34 (2H, s, NH2), 7.39-7.47 (2H, m, arom.), 7.66 (1H, t,  J = 9.0 Hz, arom.), 7.86 (1H, d, J = 9.0 Hz, arom.);  13C NMR (100 MHz, DMSO-d6, TMS) δ ppm; 20.7, 36.7, 58.2, 104.2, 113.1, 116.6, 117.8, 119.3, 122.5, 124.7, 127.6, 129.1, 132.9, 136.3, 140.5, 152.2, 153.3, 158.0, 159.6.

2.1.3. Product 4c: White solid; (purified by recrystallization with ethanol); IR (KBr) cm-1: 3370, 3290, 3182, 2191, 1709, 1671, 1605, 1571, 1507, 1459, 1379, 1319, 1251, 1178, 1111, 1052, 1026, 951, 834, 756, 564, 529;  ; 1H NMR (300 MHz, DMSO-d6 TMS) δ ppm;  3.68 (3H, s, OCH3), 4.35 (1H, s, CH), 6.82  (2H, d,  J = 8.4 Hz, arom.), 7.13  (2H, d, J = 8.4 Hz, arom.), 7.33 (2H, s, NH2), 7.38-7.47 (1H, m, arom.),7.63-7.69 (1H, m, arom.), 7.84 (1H, dd,  J = 7.5 Hz, J = 1.2 Hz, arom.), 7.93  (1H, d,  J = 9.0 Hz, arom.);  13C NMR (100 MHz, DMSO-d6, TMS) δ ppm; 36.2, 55.1, 58.4, 104.3, 114.0, 115.3, 116.6, 119.4, 122.5, 124.8, 128.8, 132.9, 133.5, 135.5, 152.2, 153.1, 158.0, 159.6, 160.5.

2.1.4. Product 4e: Light yellow colored solid; (purified by recrystallization with ethanol); IR (KBr) cm-1: 3402, 3323, 3204, 2197, 1714, 1670, 1604, 1509, 1379, 1264, 1143, 1047, 761, 481;  ; 1H NMR (300 MHz, DMSO-d6 TMS) δ ppm ; 4.46 (1H, s, CH), 7.23 (2H, d,  J = 8.4 Hz, arom.), 7.43-7.50 (6H, m, NH2 + arom.), 7.68-7.72 (1H, m, arom.), 7.88 (1H, d, J = 7.2 Hz, arom.);  13C NMR (100 MHz, DMSO-d6, TMS) δ ppm; 36.4, 57.7, 103.6, 113.1, 116.6, 119.1, 122.6, 124.8,128.6, 129.6, 131.7, 133.1, 142.4, 152.3, 153.6, 158.1, 159.7.

2.1.5. Product 4f: Yellow colored solid;  (purified by recrystallization with ethanol); IR (KBr) cm-1: 3385, 3305, 3188, 2191, 1712, 1674, 1606, 1375, 1060, 759, 510;  ; 1H NMR (300 MHz, DMSO-d6 TMS) δ ppm; 5.12 (1H, s, CH), 7.17-7.23 (3H, m, NH2 + arom.), 7.34 (3H, t,  J = 8.7 Hz, arom.), 7.46 (4H, t, J = 10.1 Hz, arom); 13C NMR (100 MHz, DMSO-d6, TMS) δ ppm; 37.0, 56.6, 116.5, 116.9, 119.5, 120.7, 124.8, 125.1, 125.8, 129.8, 130.4, 131.9, 134.5, 142.5, 150.3, 154.1, 159.0.

2.1.6. Product 4j: Yellow colored solid; (purified by recrystallization with ethanol); IR (KBr) cm-1: 3390, 3212, 3179, 2197, 1662, 1575, 1465, 1409, 1260, 1227, 746, 548; 1H NMR (300 MHz, DMSO-d6 TMS) δ ppm: 4.64 (1H, s, CH), 7.44 (2H, t,  J = 7.5 Hz, arom.), 7.49-7.54 (2H, m, arom.), 7.57 (2H, s, NH2), 7.69 (1H, t,  J = 7.5 Hz, arom.), 7.87 (1H, d, J = 7.5 Hz, arom.), 8.14 (2H, d,  J = 8.4 Hz, arom.); 13C NMR (100 MHz, DMSO-d6, TMS) δ ppm; 22.3, 36.9, 43.9, 56.9, 102.9, 113.0, 116.7, 118.9, 122.7, 123.8, 124.8, 129.2, 133.2, 146.7, 150.8, 152.4, 154.0, 158.1, 159.6.

2.1.7. Product 4k: Yellow colored solid; (purified by recrystallization with ethanol); IR (KBr) cm-1;  3382, 3235,3179, 2193, 1728, 1663, 1600, 1416, 1298, 1173, 1119, 1010, 753, 472;  1H NMR  (300 MHz, DMSO-d6 TMS) δ ppm: 4.69 (1H, s, CH), 7.42 (1H, d,  J = 8.7 Hz, arom.), 7.48 (1H, d,  J = 7.8 Hz, arom.), 7.52 (2H, s, NH2), 7.59 (1H, t,  J = 7.8 Hz, arom.), 7.68 (1H, dt, J = 8.0 Hz, J = 8.0 Hz, J = 1.4 Hz, arom.), 7.76 (1H, t, J = 7.8 Hz, arom.), 7.87 (1H, d, J =7.2 Hz, arom.), 8.08 (2H, d,  J = 7.8 Hz, arom.), 13C NMR (100 MHz, DMSO-d6, TMS) δ ppm; 22.3, 36.8, 43.9, 57.1, 103.0, 113.0, 116.7, 119.0, 122.5, 124.8, 130.2, 133.2, 134.8, 145.6, 148.0, 152.4, 154.0, 158.3, 159.7.

Result and Discussion

To pursue our work towards development of efficient methods for the synthesis of important heterocyclic compounds adopting MCRs [35], herein we became interested in developing an environmental friendly method involving use of DTP/SiO2 as an efficient, recyclable heterogenous catalyst for the synthesis of 2-amino-5-oxo-4-phenyl-4, 5-dihydropyrano[3,2-c]chromene-3-carbonitrile derivatives through a one-pot multi-component condensation reaction of 4-hydroxyquinolin-2(1H)-one, aldehydes, and malononitrile. By a preliminary experiment, we found that this three-component condensation reaction catalyzed by DTP/SiO2 worked very well. Hence, inspired by the preliminary experiments, herein we have reported an efficient one-pot multi-component synthesis of 2-amino-5-oxo-4-phenyl-4, 5-dihydropyrano [3,2-c] chromene-3-carbonitrile derivatives in excellent yields (Scheme 1).

Scheme 1. Synthetic route of 2-amino-5-oxo-4-phenyl-4, 5-dihydropyrano[3,2-c]chromene-3-carbonitrile derivatives

Initially, we investigated the three-component condensation reaction of 4-hydroxy-2H-chromen-2-one 1, benzaldehyde 2a, and malononitrile 3 in the presence of various catalyst; the results are tabulated in Table 1.

Table 1. Comparison of catalytic activity of various catalysts for synthesis of pyrano[3,2-c]chromene-3-carbonitrile derivatives

In order to optimize the reaction condition viz. catalyst loading and solvent, a model reaction was studied by varying the range of solvent including polar and non-polar solvent. In order to find out the appropriate solvent for the synthesis, the model reaction was carried out by using solvents such as methanol, ethanol, dichloromethane (DCM), acetonitrile, Dimethyl formamide (DMF). However, the DMF solvent gave the preferred pyrano[3,2-c]chromene-3-carbonitrile product in good yield (Table 1, entry 8), whereas methanol, ethanol, DCM and acetonitrile, respectively gave moderate yield (Table 1, entries 1–4). The formation of the preferred product was not observed using water as the solvent (Table 1, entry 6). This indicates that the solvent play the key role for the activity and performance of the catalyst. The above observations indicate the reaction using polar protic solvent that shows an astonishing effect on the yield of the product. Thus, with the reaction in the presence of polar protic solvent, there was negligible possibility for the substrate to come in contact with catalyst therefore, the yield of the product was found to be low, and reaction in polar aprotic solvent showed the highest yield. The promising results were observed using DMF as a solvent over a DTP/SiO2 catalyst, which allowed us to further optimize the DTP/SiO2 catalyst loading. The results in Table 1 (entry 7) reveal that the catalyst with 20 mole % of DTP/SiO2 loading is excellent. Considering the catalyst using 30 mole % DTP/SiO2 tested, there was no considerable rise in the yield of the product (Table 1, entry 8). The optimized reaction condition for the given reaction was found to be using 20 mole% DTP/SiO2 in DMF solvent. These results motivated us to explore the scope of the pyrano[3,2-c]chromene-3-carbonitrile derivatives synthesis from substituted 4-hydroxyquinolin-2(1H)-one, aldehydes, and malononitrile in the presence of a DTP/SiO2 catalyst at optimized reaction conditions.

A series of aromatic aldehydes were selected to undergo the condensation in the presence of DTP/SiO2 catalyst. As shown in Table 2, aromatic aldehydes 2 carrying either electron-donating or electron-withdrawing substituent reacted efficiently and gave excellent yields (Table 2, entries 1–14). The possible mechanism is depicted in scheme 2 in the supplementary file.

Therefore, the nature of the substituents attached to the aromatic ring did not show significant effect in this conversion. The experimental operations involved efficient, eco-friendly, convenient, rapid properties and showed the ability to endure a variety of electron releasing and electron withdrawing functional groups, such as methoxyl, nitro, hydroxyl, and halides. The recycling experiment revealed that the catalyst could be recycled for next 4-5 times reaction without further purification of the catalyst. And it was observed that there was no significant loss in the yield of the product (Table-3).

Conclusion

In summary, we have reported a simple, rapid, efficient one-pot multi-component condensation of 4-hydroxyquinolin-2(1H)-one 1, aldehyde 2, malononitrile 3 catalyzed by efficient heterogeneous catalyst DTP/SiO2 to offer 2-amino-5-oxo-4-phenyl-4, 5-dihydropyrano [3,2-c] chromene-3-carbonitrile derivatives 4. The current method offers simple experimental procedure, easy isolation of catalyst, efficacy and reusability of the catalyst over the previously reported methods.

Acknowledgments

The author RDK thankful to BOD, Savitribai Phule Pune University, Pune for ASPIRE Research Grant (18TCR000044) and author MVG gratefully acknowledge to Savitribai Phule Pune University, Pune for Minor Research Grant.

Orcid:

Rahul D. Kamble: https://orcid.org/0000-0003-4994-9818 

Milind V. Gaikwad: https://orcid.org/0000-0001-5917-6455  

Manojkumar R. Tapare: https://orcid.org/0000-0003-1968-9189     

Shrikant V. Hese: https://orcid.org/0000-0002-5274-1148 

Shuddhodan N. Kadam: https://orcid.org/0000-0003-3791-3498 

Ajay N. Ambhore: https://orcid.org/0000-0002-0993-2440   

Bhaskar S. Dawane: https://orcid.org/0000-0003-2359-90182

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[1] M.Y. Pathan, S.S. Chavan, T.M.Y. Shaikh, S.H. Thorat, R.G. Gonnade, S.A.R. Mulla, Chemistry Select, 2017, 2(28), 9147-9152. [crossref], [Google Scholar], [Publisher]  
[2] S.A.R. Mulla, M.Y. Pathan, S.S. Chavan, S.P. Gample, D. Sarkarb, RSC Adv., 2014, 4, 7666-7672. [crossref], [Google Scholar], [Publisher]
[3] S.A.R. Mulla, M.Y. Pathan, S.S. Chava, RSC Adv., 2013, 3, 20281-20286. [crossref], [Google Scholar], [Publisher]
[4] M.Y. Pathan, S.S. Chavan, T.M.Y. Shaikh, S.H. Thorat, R.G. Gonnade, S.A.R. Mulla, Chemistry Select, 2017, 2(28), 9147-9152. [crossref], [Google Scholar], [Publisher]
[5] L.S. Roselin, R. Selvin, P. Aneesh, Kinet Catal., 2011, 52, 823–827. [crossref], [Google Scholar], [Publisher]
[6] U.A.A. Mohammad, S.A. Khayyat, S. Rosilda, Sci. of Adv. Mat., 2015, 7, 2452-2458. [crossref], [Google Scholar], [Publisher]
[7] S. Kumar, D. Hernandez, B. Hoa, Y. Lee, J.S. Yang, A. McCurdy, Org. Lett., 2008, 10, 3761–3764. [crossref], [Google Scholar], [Publisher]
[8] C.N. O’Callaghan, T.H.B. McMurry, J. Chem. Res., 1995, 214-217. [Pdf], [Google Scholar], [Publisher]
[9] A.H. Adbel-Fattah, A.M. Hesien, S.A. Metwally, M.H. Elnagdi, Liebigs Ann. Chem., 1989, 585–588. [crossref], [Google Scholar], [Publisher]
[10] J.M. Quintela, C. Peinador, M.J. Moreira, Tetrahedron, 1995, 51, 5901–5912. [crossref], [Google Scholar], [Publisher]
[11] S.V. GAIKWAD, M.V Gaikwad, P.D. Lokhande, J. Appl. Organomet. Chem., 2021, 1, 1-8. [crossref], [Pdf], [Publisher]; (b) B.S. Hote, D.B. Muley, G.G. Mandawad, J. Appl. Organomet. Chem., 2021, 1, 9-16. [crossref], [Pdf], [Publisher]
 
[12] G.R. Green, J.M. Evans, A.K. Vong, A.R. 00Katritzky, C.W.E.F. Rees, Scriven(Eds.), Comprehensive Heterocyclic Chemistry II, 5, Pergamon Press, Oxford, 1995, pp. 469-471. [Google Scholar], [Publisher]
[13] W.O. Foye, Principi Di Chemico Farmaceutic. Piccin, Padova, Italy, 1991, 416-420. [Google Scholar], [Publisher]
[14] M.M. Khafagy, A.H.F.A. El-Wahab, F.A. Eid, A.M. El-Agrody, Farmaco 2002, 57, 715-722. [crossref], [Google Scholar], [Publisher]  
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