Synthesis of benzoimidazoquinazolinone and indolylxanthenone derivatives using Keggin- type heteropoly-11-molybdo-1-vanadophosphoric acid supported on Montmorillonite K-10 clay as catalyst: A green approach

doi:10.21203/rs.3.rs-1963641/v1

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Synthesis of benzoimidazoquinazolinone and indolylxanthenone derivatives using Keggin- type heteropoly-11-molybdo-1-vanadophosphoric acid supported on Montmorillonite K-10 clay as catalyst: A green approach

https://doi.org/10.21203/rs.3.rs-1963641/v1

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A new green protocol for the synthesis of benzoimidazoquinazolinone and indolylxanthenone derivatives were attained under environmental-friendly solvent-free condition through a simple one-pot three component condensation reaction using 10% heteropoly-11-molybdo-1-vanadophosphoric acid (H₄[PVMo₁₁O₄₀]) loaded on Montmorillonite K-10 clay material (PVMoK-10) as an efficient heterogeneous catalyst. The identification and characterization of the derivatives were done by physical as well as spectral techniques. Synthesis of ten derivatives of benzo[4,5]imidazo[2,1-b]quinazolin-1(2H)-one and two derivatives of 9-(1H-indol-3-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-onewere successfully achieved using this protocol.A tentative reaction mechanism has also been proposed for the synthetic plans.

One-pot multi-component synthesis

Heteropoly acid supported Montmorillonite K-10 clay catalyst

Benzoimidazoquinazolinone

Indolylxanthenone

Heterocyclic compounds are renowned for their diversified and potential biological activity essential for everyday life [1-6]. More specifically, the nitrogen containing heterocyclic moieties are more active in the biological and the pharmacological areas [7-9] because of their resemblance of structure with some naturally existing organic molecules, which shows familiar biological activity [4]. Furthermore, the review of literature reveals that, polyheterocyclic molecular entity enhances the biological versatility of the natural product [10]. This part of the work dealt with the synthesis of two such types of polyheterocyclic compounds viz., benzoimidazoquinazolinones and indolylxanthenones.

Benzoimidazoquinazolinone contains benzimidazole as well as quinazoline moieties in its structure. Both the heterocycles have been attracted extensively by synthetic organic as well as medicinal chemists, due to their diversified applications in the multitude of areas [11-14]. On the other hand, indolylxanthenones have both indole and xanthene moieties. The chromene part of xanthene is one of the more privileged scaffolds in natural products [15]. They are found to be a valuable precedence motif for designing pharmacophore in the area of medicinal chemistry for the development of drugs [16, 17, 18]. Organic chemists are more concerned with devising synthetic strategies for the synthesis of such biologically active organic molecules. MCRs diligently have been admired due to their powerful upshot on drug innovation for their sharp focus in shortening the synthetic pathway of drugs and their derivative products [19-23]. Tayebee et-al [24-31] have successfully attempted many novel protocols to synthesise biologically active organic molecules using heteropolyoxometalate-supported catalysts through MCRs. This research work is one such attempt to develop a new synthetic protocol for the syntheses of benzoimidazoquinazolinones and indolylxanthenones using heteropolyoxometallate supported catalysts under environmentally benign reaction conditions.

A review of the literature finds that a few synthetic approaches have been reported for the synthesis of benzimidazoquinazolinesincluding its synthesis through a three-component condensation of 2-aminobenzimidazole, 1,3-cyclohexadione and substituted aromatic aldehydes in the presence of catalyst silica gel under solvent free condition [32]. Ali Maleki et-al[33] reported thesynthesis of Benzimidazolo[2,3-b]quinazolinone derivatives through a one-pot multicomponent reaction promoted by a Chitosan-based composite magnetic nanocatalyst. Ziarani et-al[34] proposed a synthetic route for the synthesis of benzimidazoquinazolinones using nanoporous Santa Barbara Amorphous-15 silica (SBA-15).

Functionalized on sulfonic acid (SBA-Pr-SO₃H) as heterogeneous acid catalyst via the reaction of substituted aldehydes with a cyclic1,3- diketone and 2- aminobenzimidazole under solvent-free condition.Heravi et-al [35] proposed the synthesis of triazoloquinazolinones and benzimidazoquinazolinones by the condensation reaction of amine sources like 3-amino-1,2,4-triazole/2-amino benzimidazole with aldehydes and dimedone using acetonitrile mediated sulfamic acid catalyst under reflux condition.Mousavi et-al [36] proposed synthesis of derivatives of [1,2,4]triazolo[5,1‑b] quinazolin‑8(4H)‑one and hexahydro[4,5]benzimidazolo[2,1‑b]quinazolinone by the reaction of substituted aldehydes with dimedone and 3-amino-1,2,4-triazole/2-aminobenzimidazole using acetic acid promoter under metal-free condition at 60^oC.Mousavi et-al [37] developed an eco-friendly synthesis of triazoloquinazolinones and benzimidazoquinazolinones derivatives via the condensation reaction of substituted aromatic aldehydes with cyclic 1,3-diketone and 3-amino-1,2,4-triazole/2-amino benzimidazole by heterogeneous nano-SiO₂ catalyst in acetonitrile medium at room temperature. Yao et-al [38] accomplished the synthesis of 4-aryl-1H-pyrimido[1,2-a] benzimidazole derivatives by the condensation of substituted aryl aldehyde and 2-aminobenzimidazole with 1,3-dicarbonyl compounds in 1-butyl-3-methyl imidazolium tetrafluoroborate ([bmim⁺][BF^4-]) ionic liquid medium at 90^oC. Mousavi et-al [39] proposed the synthesis of triazoloquinazolinone and benzimidazoquinazolinone derivatives via the condensation reaction of different aryl aldehydes and cyclic1,3-dicarbonyl compound with 2-aminobenzimidazole/3-amino-1,2,4-triazole catalysed by p-toluenesulfonic acid monohydrate at 40-50^oC in acetonitrile reaction medium. Puligoundla et-al [40] reported the synthesis of benzimidazoloquinazolinone derivatives through the condensation of an amino source, 2-aminobenzimidazole, aryl aldehyde and dimedone. The reaction was mediated by molecular iodine in acetonitrile solvent medium under reflux condition for about 15 min. Heravi et-al[41] developed the synthesis of [1,2,4]triazolo/benzimidazolo-quinazolinone derivatives by refluxing 3-amino-1,2,4-triazole / 2-amino benzimidazole with dimedone and aromatic aldehyde using Wells-Dawson type heteropoly acid, H₆[P₂W₁₈O₆₂]18H₂O as catalyst in acetonitrile solvent medium. Petrova et-al [42] developed a three-component condensation reaction of arylglyoxals, 2-aminobenzimidazole and 1,3-cyclohexanedione under conventional as well as microwave conditions. Mourad et-al [43] reported the microwave mediated synthesis of benzimidazoquinazolinones via the reaction of 2-aminobenzimidazole with aryl aldehydes and dimedone in dimethylformamide. Kasaralikar et-al[44] reported the synthesis of oxochromenyl xanthenone / indolyl xanthenone derivatives via the condensation of various substituted salicylaldehydes and 4-hydroxy coumarin/indole with dimedone at room temperature using an ionic liquid 1-hexyl-3-methylimidazolium hydrogen sulphate, ([Hmim]HSO₄) catalyst in ethanolic medium at 50^oC.Bhattacharjee et-al [45] performed the synthesis of 9-(1H-Indol-3-yl)-3,3-dimethyl-2,3,4,9-tetrahydro-1H-xanthen-1-one using ammonium chloride in aqueous medium via a condensation reaction of salicylaldehyde with cyclic 1,3-diketones and indole. Ganguly et-al [46] accomplished L-proline mediated coupling reaction of 2-hydroxybenzaldehyde with indole and 5,5-dimethyl-1,3-cyclohexanedione for the synthesis of 9-(1H-indol-3-yl)-xanthen-4-(9H)-ones under micellar condition using sodium dodecyl sulphate in water at ambient temperature.

In spite of their pre-eminence of the aforementioned synthetic protocols, the synthesis of benzimidazoquinazolines and indolylxanthenone are perceived to be deprived of easy, simple, greener and direct methods. The discovery of simpler and greener method for the synthesis is of utmost significance and is essential for overcoming these difficulties by the emergence of a simpler and greener method. Subsequently, it is planned to prepare benzimidazoquinazolines and indolylxanthenone in new methodology. In continuation of our successful previous green synthetic protocol for the synthesis of several organic heterocyclic compounds [47-51].Herein, we devised a simple and economical strategy to synthesize benzo[4,5]imidazo[2,1-b]quinazolin-1(2H)-one derivatives (R1) by condensation of 1,3-cyclohexadione with 2-aminobenzimidazole, and various substituted aldehydes and 9-(1H-indol-3-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one derivatives (R2) through the condensation reaction of indole, 1,3-cyclohexadione and salicylaldehyde at 100 ^oC under solvent-free medium using a heterogeneous catalyst heteropoly-11-molybdo-1-vanadophosphoric acid, H₄[PVMo₁₁O₄₀]-supported on the clay material MontmorilloniteK-10 clay (PVMoK-10).

Materials and methods

1,3-cyclohexadione, 2-aminobenzimidazole, indole, different substituted aldehydes and Montmorillonite K-10 clay (Mont-K10)were purchased from Sigma-Aldrich and all were used as such without further purification. The 12-heteropoly acid (HPA) H₃[PMo₁₂O₄₀], its mono-vanadium (V) substituted HPA,H₄[PVMo₁₁O₄₀], di-vanadium (V) substituted HPA, H₅[PV₂Mo₁₀O₄₀] and the HPAs supported Mont-K10 with different loadings of HPA viz.10%, 20% and 30% in (w/w) were prepared and characterized using the procedures reported in the literature [52-54].

General reaction procedure for the synthesis of benzo[4,5]imidazo[2,1-b]quinazolin-1(2H)-onederivatives (R1)

Benzo[4,5] imidazo[2,1-b]quinazolin-1(2H)-one derivatives were prepared as per the procedure adopted in literature [35, 55]. A mixture of one millimole each of undefined2-aminobenzimidazole, 1,3-cyclohexadione, substituted aromatic aldehyde and 0.05g of the catalyst 10% PVMoK-10 were heated at 100^oC for 1h in oil bath. The proceeding of the conversion was followed by TLC using petroleum ether – ethyl acetate solvent mixture in the ratio 7:3. After the completion of the reaction was ascertained through TLC, 5 mL of ethanol was added to the reaction mixture and the mixture was heated. The organic product thus formed was soluble in ethanol. The solid catalyst from the reaction mixture was removed by filtration. The filtrate was then poured into crushed ice pieces and the solid product isolated was filtered out. The product formed was washed thoroughly with water, dried and recrystallized from ethanol. The recovered catalyst by filtration method was thoroughly washed with water and dried in air oven for about an hour at 100^oC.

General reaction procedure for the synthesis of 9-(1H-indol-3-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-onederivatives (R2)

9-(1H-indol-3-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one derivatives were prepared as per the procedure reported in the literature [55-57]. One millimole each of indole, 1,3-cyclohexadione, salicylaldehyde were mixed with 0.05g of 10% PVMoK-10 and heated for about 1h at 100^oC in an oil bath. The completion of the reaction was followed by TLC using the eluent ethyl acetate and n-hexane solvent in the ratio 7:3. After the reaction is over, 5 mL of ethanol was added in order to dissolve the organic product formed. The solid catalyst from the reaction mixture, was filtered out while hot. A solid product was regenerated by pouring the filtrate into water and the solid separated out was filtered off, washed thoroughly with water, dried well and recrystallized using solvent ethanol. The recovered catalyst by filtration was washed thoroughly with water and dried in air oven at 100^oC for about an hour.

IR Affinity-1 Shimadzu FT-IR spectrophotometer isused for recording Fourier transform infrared (FT-IR) spectra,under atmospheric conditions using KBr pellets. Bruker400 MHz NMR instrument is utilized for recording proton and ¹³C NMR with DMSO-d₆as solvent and tetramethylsilane as internal standard. Melting points of samples were noted by the electro thermal melting point apparatus. Elemental analyses were studied usingElementarVario EL III equipment. High-resolution mass spectra (HRMS) was recorded using the maXis Impact 282001.00081 Mass Spectrometer for the selected products.

Optimization of catalyst

The efficacy of the catalyst was investigated by choosing the condensation reaction of 2-aminobenzimidazole, 1,3-cyclohexadione with benzaldehyde in the presence of catalyst as a model reaction for the preparation of R1 and the condensation of indole, 1,3-cyclohexadione and salicylaldehyde in the presence of catalyst for the preparation of the R2. The reactions were strived with various catalytic materials such as raw Mont K-10, HPAs viz., H₃[PMo₁₂O₄₀] (PMo), H₄[PVMo₁₁O₄₀] (PVMo) and H₅[PV₂Mo₁₀O₄₀] (PV₂Mo) & 10% HPAs loaded Mont K-10 clay, PVMoK-10 and PV₂MoK-10. Product yield in percentages was used to assess the performance of the selected catalyst, and the results are summarised in Table 1. Clearly, the results reveal that the performance of 10% catalysts-PVMoK-10 & PV₂Mo-K10 are found to be very high compared to both raw Mont-K10 clay and vanadium substituted heteropoly acids. Both vanadium (V) substituted HPAs loaded Mont-K10 clay show more or less similar catalytic efficacy. Hence, PVMoK-10 has been selected as catalyst for the current investigation.

Table 1. Optimization of catalyst for one-pot three component synthesis of 12-phenyl-3,4,5,12-tetrahydrobenzo[4,5]imidazo[2,1-b]quinazolin-1(2H)-one and 9-(1H-indol-3-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one derivative^a

Run	Catalyst	Catalyst amount (g)	Yield^b (%)
				R1	R2
1.	Mont-K10	0.05	43 51 62 65 75 94 95	42	39
2.	PMo	0.05		48	47
3.	PVMo	0.05		54	56
4.	PV₂Mo	0.05		66	59
5.	PMo-K10	0.05		74	62
6.	PVMo-K10	0.05		94	88
7.	PV₂Mo-K10	0.05		92	88

Reaction conditions: R1: 2-aminobenzimidazole (1 mmol), 1,3-cyclohexadione (1 mmol) and benzaldehyde (1 mmol), Solvent-free condition, 100 °C, 1h.

R2: Indole (1 mmol), 1,3-cyclohexadione (1 mmol) and salicylaldehyde (1 mmol), Solvent-free condition, 100 °C, 1h.

^bIsolated Yields.

Dependency of different loadings of PVMo on Mont K-10 clay

The catalytic performances of PVMo loaded Mont K-10 for about 5 %, 10 %, 30 % and 40 % were evolved for both the reactions as per the reported procedure [51]. The efficiency of the catalysts was evaluated in terms of percentage yield of products (R1 and R2). The results are summarised in Table 2. It is found that the 10% PVMoK-10 showed equivalent efficiency as that of 20% and 30% loading of PVMo on Mont-K10 and hence 10% PVMoK-10 has been selected as the catalyst to perform the present synthetic transformation.

Table 2. Effect of different loadings of PVMo on Mont-K10 in synthesis of 12-phenyl-3,4,5,12-tetrahydrobenzo[4,5]imidazo[2,1-b]quinazolin-1(2H)-one and 9-(1H-indol-3-yl)-2,3,4,9-tetrahydro-1H-xanthen-1-one derivative^a

Run	% of loading of PVMo on Mont-K10	Catalyst amount (g)	Yield^b (%)
Run	% of loading of PVMo on Mont-K10	Catalyst amount (g)	R1	R2
1.	5	0.05	73	71
2.	10	0.05	94	88
3.	20	0.05	95	88
4.	30	0.05	95	89

^aReaction conditions: R1: 2-aminobenzimidazole (1 mmol), 1,3-cyclohexadione (1 mmol) and benzaldehyde (1 mmol), Solvent-free condition, 100 °C, 1h.

R2: Indole (1 mmol), 1,3-cyclohexadione (1 mmol) and salicylaldehyde (1 mmol), Solvent-free condition, 100 °C, 1h.

^bIsolated Yields.

Dependency of solvents

The reactions were run in different solvent media such as EtOH, MeOH, H2O, MeCN, DCE, DMF, CHCl3, 1,4-dioxane, n-hexane and toluene at elevated temperature (refluxing for an hour). The reaction was also attempted under solvent-free reaction condition. The results of the experiments in terms of yield of products R1 and R2 are given in Table 3. The results favours the solvent-free reaction condition for the present synthetic transformation since the yield of products under this condition is excellent.

Table 3. Dependency of different solvent medium for synthesis R1 & R2 catalyzed by 10%PVMoK-10 ^a

S. No	Solvent used	Yield^b(%)
S. No	Solvent used	R1	R2
1	EtOH	57	51
2	MeOH	71	64
3	H2O	31	27
4	CH₃CN	28	22
5	DCE	57	53
6	DMF	30	26
7	CHCl₃	39	33
8	1,4-dioxane	32	28
9	n-Hexane	40	42
10	Toluene	55	49
11^c	Solvent free	94	88

^aReaction conditions: R1: 1,3-cyclohexadione (1 mmol), 2-aminobenzimidazole (1 mmol) and benzaldehyde (1 mmol), Solvent-free condition, 10% PVMo-K10 0.05 g, Stirring at 1 h.

R2: 1,3-cyclohexadione(1mmol), Indole (1 mmol) and salicylaldehyde (1 mmol), Solvent-free condition, 10% PVMo-K10 0.05 g, Stirring at 1 h.

^bIsolated Yields, ^c100 °C.

Synthesis of benzimidazoquinazolinone derivatives

The optimized reaction procedure has been adapted for the preparation of ten derivatives of R1 (4a – 4j) using 2-aminobenzimidazole, 1,3-cyclohexadione and ten structurally diverse aldehydes. The reaction pattern is schematically explained in Scheme 1 and the results are consolidated in Table 4.

Synthesis of indolylxanthenone derivatives

Similarly, the optimized reaction procedure has been adapted for the preparation of two derivatives of R2 (4k and 4l) using 1,3-cyclohexadione, salicylaldehyde and two different indoles. The reaction pattern is schematically explained in Scheme 2 and the results are consolidated in Table 5.

With the help of above procedure, ten different R1 derivatives (4a-4j) and two different R2 derivatives (4k and 4l) have been synthesized through one-pot reaction condition using 10% PVMoK-10 catalyst in solvent-free reaction condition. The details of specific reactants used, products formed (4a-4l) and their percentages of yields are collected in Table 4 and 5.

Further HRMS (Fig.1) of optimized reaction product 12-phenyl-3,4,5,12-tetrahydrobenzo[4,5]imidazo[2,1-b]quinazolin-1(2H)-one (4a) with the molecular ion peak at 315.0428 confirms the formation of the expected product. Analytical as well as the spectral data of the compounds 4a- l are appended as supplementary materials.

Tentative mechanism

The tentative mechanism for the synthesis of R1 derivatives using 10% PVMoK-10 catalyst as a promoter has been arrived based on the mechanism reported by Jolodar and Shirini [58] and is shown in Scheme 3. The catalysis involves the following sequence:

(i) The nucleophilic attack of enol form of 1,3-cyclohexadione on the carbonyl carbon of aldehyde leads to the formation of intermediate (I)

(ii) Dehydration of the intermediate (I) forms intermediate (II)

(iii) The hastening of the nucleophilic attack of the amine group on intermediate (II) leads to the formation of (IV) through the intermediate (III) and

(iv) Dehydration of (IV) leads to the formation of desired product.

10 % loaded solid heteropoly acid, PVMo on Mont K-10 catalytic material accelerates the organic transformation.

The plausible mechanism for the synthesis of R2 derivatives using 10% PVMoK-10 as a promoter has been arrived as per the mechanisms reported in the literature [44, 45] and is shown in Scheme 4. The reaction sequence is given as follows:

(i) The nucleophilic attack of enol form of 1,3-cyclohexadione on the carbonyl carbon of salicylaldehyde leads to the formation of intermediate (I).

(ii) The nucleophile indole reacts at the benzylidene double bond of the intermediate (I) which further experiences ring-closure reaction intra-molecularly followed by dehydration and give the desired product.

The primary role of heteropoly acid is a source of proton, which activates the carbonyl group.

Recycling of the catalyst

The separation of the catalyst and its reusability are the two most important criteria for the green catalysts.

In the present investigation, the catalyst from the reaction mixture wasseparated by simply adding excess ethanol with the fused mass produced at the end of the condensation reaction. The product obtained wasdissolved in ethanol whereas the catalyst was separated from the reaction mixture as insoluble residue, filtered off, washed thoroughly with ethanol and dried in hot air oven for an hour at 120 ^oC.The catalyst thus recovered was reused under the same reaction conditions. It was observed that the reuse of the catalytic material 10% PVMo-K10 showed gradual decrease in its activity. The consecutive performance of the catalyst thus recovered was examined in terms of its % yield of the products and was found to be sustainable for about five times.

An environmentally benign approach has been devised for one-pot three component synthesis of ten derivatives of R1 and two derivatives of R2 under solvent-free reaction medium, catalyzed by 10%PVMoK-10 heterogeneous catalyst. About five times of reusing the catalyst is possible without significantly losing its catalytic activity. This approach has a number of advantages, including a short reaction time, better yield, the capacity to reuse the catalytic material, and a simplified setup process under environment friendly experimental studies.

Acknowledgements

The authors thank the Managing Board authorities of Virudhunagar Hindu Nadars’ Senthikumara Nadar College (Autonomous), Virudhunagar-626001, Tamil Nadu, India for providing infrastructural and research facilities.

Supporting information

Complete analytical details, ¹H, ¹³C NMR, FT-IR spectral data of the compounds 4 (a) – 4 (l) and HRMS data for 4(a) and 4 (k) are appended as Supplementary materials.

Ethical Approval

This declaration is not applicable

Competing interests

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.

Authors' contributions

Antony Muthu Prasanna and Murugan Kumaresan: Conceptualization, Methodology, Investigation, Formal analysis, Writing -original draft.

Karuppaiah Selvakumar and Meenakshisundaram Swaminathan: Data curation and spectral verification

Ponnusamy Sami : Resources, Formal analysis and Supervision.

Funding

Not applicable

Availability of data and materials

Not applicable

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Tables 4- 5 are available in the Supplementary Files section.

Schemes 1-4 are available in the Supplementary Files section.

No competing interests reported.

APSupplimentarydata15.08.2022.docx
Table45.docx
Scheme01.png
Scheme 1 Synthesis of R1 derivatives (4a - 4j) catalyzed by 10% PVMoK-10 as catalyst.
Scheme02.png
Scheme 2 Synthesis of R2 derivatives (4k and 4l) using 10% PVMoK-10 as catalyst.
Scheme03.png
Scheme 3: Tentative reaction pathway for benzoimidazoquinazolinone synthesis using 10% PVMoK-10 as catalyst
Scheme04.png
Scheme 4: Tentative reaction pathway for synthesis of indolylxanthenone derivatives catalyzed by 10% PVMoK-10 as catalyst

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Synthesis of benzoimidazoquinazolinone and indolylxanthenone derivatives using Keggin- type heteropoly-11-molybdo-1-vanadophosphoric acid supported on Montmorillonite K-10 clay as catalyst: A green approach

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