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Application of \(\hbox {SiO}_{{2}}\) nanoparticles as an efficient catalyst to develop syntheses of perimidines and tetraketones

  • Heshmatollah AlinezhadEmail author
  • Armin Ahmadi
  • Parvin Hajiabbasi
Regular Article
  • 59 Downloads

Abstract

In this paper, we explore the catalytic activity of \(\hbox {SiO}_{{2}}\) nanoparticles (NPs) as an eco-friendly, efficient and reusable catalyst in the synthesis of 2,3-dihydro-1H-perimidines as well as tetraketones. For tetraketones syntheses, a simple tandem Knoevenagel condensation following Michael addition procedure is performed by the reaction between benzaldehydes and 5,5-dimethyl-1,3-cyclohexanediones under solvent-free condition using \(\hbox {SiO}_{{2}}\) NPs as an efficient solid catalyst. In addition, for 2,3-dihydro-1H-perimidines syntheses, cyclocondensation of various aldehydes with 1,8-diaminonaphthalene is achieved under solvent-free condition using \(\hbox {SiO}_{{2}}\) NPs as a catalyst at room temperature. The results showed catalytic enhancement in both synthetic procedures. In this work, 4-(2,3-dihydro-1H-perimidin-2-yl)benzonitrile and 2-(pyridin-4-yl)-2,3-dihydro-1H-perimidine are synthesized as new compounds. Also, reusability study of \(\hbox {SiO}_{{2}}\) NPs was done to ensure its applicability as a recycled catalyst in this work.

Graphical Abstract

  The catalytic activity of \(\hbox {SiO}_{{2}}\) nanoparticles (NPs) as an eco-friendly, efficient and reusable catalyst in the synthesis of 2,3-dihydro-1H-perimidines as well as tetraketones is explored. For tetraketones syntheses, a simple tandem Knoevenagel condensation following Michael addition procedure is performed by the reaction between benzaldehydes and 5,5-dimethyl-1,3-cyclohexanediones under solvent-free condition using \(\hbox {SiO}_{{2}}\) NPs as an efficient solid catalyst.

Keywords

2,3-Dihydro-1H-perimidines green synthesis nano-\(\hbox {SiO}_{{2}}\) solid catalyst solvent-free tetraketone derivatives 

1 Introduction

Nanoparticles are particles that exist on a nanometre range (i.e., below 100 nm in at least one dimension). They can possess physical properties such as uniformity, conductance or special optical properties that make them desirable in materials science and biology. Inorganic nanoparticles such as \(\hbox {SiO}_{{2}}\) nanoparticles (NPs) have attracted considerable attention because of their potential importance in technological applications (e.g., catalysts, filler for polymers, pigments, pharmacy, electronics and thin film substrates, electronic and thermal insulators, and humidity sensors and so on).[1, 2, 3] Moreover, homogeneous catalysts have many deficiencies in industrial and laboratory processes such as handling, corrosiveness, difficult separation and toxicity of waste. Indeed, most novel solid catalysts are based on silica due to their excellent stability (chemical and thermal), high surface area, and good accessibility of reactive centers.[4, 5, 6, 7, 8, 9]

Perimidine derivatives are attractive either for their biological activities such as antifungal, antimicrobial, antiulcer and antitumor agents[10] or for their application as intermediates in organic synthesis.[11, 12] In addition, tetraketones are also extensively used as important precursors for the synthesis of various acridinediones as laser dyes,[13, 14] DNA intercalator,[15] electron donors and acceptors[16, 17, 18] of the photoinitiated polymerization of acrylates and methacrylates,[19] and synthesis of some heterocyclic compounds.[20, 21, 22, 23]

Due to our interest in developing a new synthesis in the field of catalyst applications,[24, 25, 26, 27] herein, we explore the catalytic activity of \(\hbox {SiO}_{{2}}\) NPs as an eco-friendly, efficient and reusable catalyst in the synthesis of 2,3-dihydro-1H-perimidines as well as tetraketones. In this work 4-(2,3-dihydro-1H-perimidin-2-yl)benzonitrile and 2-(pyridin-4-yl)-2,3-dihydro-1H-perimidine are synthesized as new compounds. Although several approaches for the synthesis of both skeletons have been reported,[28, 29, 30, 31, 32, 33, 34, 35] development of simple and convenient synthetic procedures is attractive for research in synthetic organic chemistry.

2 Experimental

2.1 General information

All chemicals were used without further purification and purchased from commercial sources as follows: 1,8-diaminonaphthalene (Sigma-Aldrich-99%), dimedone (Sigma-Aldrich-97%), benzaldehyde (Sigma-Aldrich->99%), Tetraethoxysilane (Sigma-Aldrich-98%). Other chemicals and solvents were prepared commercially without further purification. IR spectra were recorded from KBr disk using an FT-IR Bruker Tensor 27 instrument. Melting points were measured by using the capillary tube method with a thermal scientific 1900 apparatus. The progress of reactions was monitored by thin-layer chromatography (TLC) on 0.2 mm silica gel F-252 (Merck) plates using n-hexane/ethyl acetate as eluent. The \(^{1}\)H NMR (400 MHz) and \(^{13}\)C NMR (100 MHz) was run on a Bruker DPX using TMS as an internal standard. Scanning Electron Microscopy (SEM) analysis was recorded on an electron microscope model Tescan Vega MV 2300T/40.

2.2 Preparation of silica nanoparticles

Tetraethoxysilane (TEOS) and aqueous ammonia 25% were separately dissolved in ethanol. Then, these two solutions were mixed and stirred for 24 h to obtained white suspension. The particles in the suspension were collected by centrifugation and dried in vacuum for 12 h to produce silica nanoparticles as the literature reported.[38]

2.3 General procedure for the preparation of 2,3-dihydro-1H-perimidine derivatives (3a3p)

The mixture of 1,8-diaminonaphthalene (1.0 mmol), carbonyl compound (1.0 mmol) and \(\hbox {SiO}_{{2}}\) NPs (0.001 g, 2 mol%) was ground by mortar and pestle at room temperature for an appropriate time. After completion of the reaction as monitored by TLC, the mixture was dissolved in ethyl acetate; then the catalyst was isolated by centrifuging and the solvent was evaporated to yield the crude product (3a3p).

2.3.1 4-(2,3-Dihydro-1H-perimidin-2-yl)benzonitrile(3j)

Brown powder. M.p.: 177–179 \({^{\circ }}\)C. \(^{1}\)H NMR (400 MHz, DMSO-\(d_{6})\): \(\delta \) 5.48 (s, 1H, N-CH-N), 6.49 (s, 2H, NH), 6.94–7.00 (m, 4H, ArH), 7.14 (t, 2H, ArH), 7.75 (d, \(J=8.0\) Hz, 2H, ArH), 7.87 (d, \(J=8.4\) Hz, 2H, ArH).\(^{ 13}\)C NMR (100 MHz, DMSO-\(d_{6})\): \(\delta \) 60.22, 104.96, 111.40, 112.82, 115.96, 119.23, 127.39, 129.19, 132.70, 134.74, 142.64, 148.27.

2.3.2 2-(Thiophen-2-yl)-2,3-dihydro-1H-perimidine(3n)

Light yellow powder. M.p.: 115–117 \({^{\circ }}\)C. \(^{1}\)H NMR (400 MHz, DMSO-\(d_{6})\): \(\delta \) 5.49 (s, 1H, N-CH-N), 6.48 (s, 2H, NH), 6.78 (m, 2H, ArH), 6.95 (d, \(J=7.6\) Hz, 2H, ArH), 7.12 (m, 2H, ArH), 7.28 (m, 1H, ArH), 7.52 (m, 1H, ArH), 7.54 (m, 1H, ArH). \(^{13}\)C NMR (100 MHz, DMSO-\(d_{6})\): \(\delta \) 62.46, 104.85, 113.04, 115.70, 124.05, 126.68, 127.32, 127.50, 134.82, 143.17, 144.44.

2.3.3 2-(Pyridin-4-yl)-2,3-dihydro-1H-perimidine(3o)

Light yellow powder. M.p.: 162–163 \({^{\circ }}\)C. \(^{1}\)H NMR (400 MHz, DMSO-\(d_{6})\): \(\delta \) 5.42 (s, 1H, N-CH-N), 6.50 (s, 2H, NH), 6.98 (m, 2H, ArH), 7.14 (m, 2H, ArH), 7.54 (m, 2H, ArH), 8.57 (m, 2H, ArH). \(^{13}\)C NMR (100 MHz, DMSO-\(d_{6})\): \(\delta \) 64.84, 105.01, 112.90, 115.96, 123.06, 127.40, 130.08, 134.74, 142.46, 150.10, 151.43.

2.4 General procedure for the preparation of tetraketone derivatives (9a9p)

A mixture of dimedones (2 mmol), benzaldehydes (1 mmol) and \(\hbox {SiO}_{{2}}\) NPs (2 mol%, 0.001 g) was heated at 110 \({^{\circ }}\)C under solvent-free condition. After completion of the reaction monitored by TLC, 5 mL THF was added to the reaction mixture. Then after isolating the catalyst by centrifuging, the solvent was evaporated to yield the crude products 2,2\(^\prime \)-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1,3-dione) (9a9p).

2.4.1 2,2\(^\prime \)-(Phenylmethylene)bis(5,5-dimethylcyclohexane-1,3-dione) (9a)

M.p.: 194–195 \({^{\circ }}\)C. \(^{1}\)H NMR (400 MHz, \(\hbox {CDCl}_{3})\): \(\delta \) 1.12 (s, 6H, Me), 1.26 (s, 6H, Me), 2.30–2.50 (m, 8H, \(\hbox {CH}_{2})\), 5.56 (s, 1H, CH), 7.11 (m, 2H, ArH), 7.19 (m, 1H, ArH), 7.21 (m, 1H, ArH), 7.29 (m, 1H, ArH), 11.93 (s, 1H, OH).\(^{ 13}\)C NMR (100 MHz, \(\hbox {CDCl}_{3})\): \(\delta \) 27.40, 29.60, 31.42, 32.73, 46.45, 47.06, 115.59, 125.85, 126.77, 128.22, 138.06, 189.41, 190.49.
Table 1

Syntheses of 2,3-dihydro-1H-perimidine derivatives catalyzed by \(\hbox {SiO}_{{2}}\) NPs.

2.4.2 2,2\(^{\prime }\)-((4-Chlorophenyl)methylene)bis(5,5-dimethylcyclohexane-1,3-dione) (9c)

M.p.: 136–138 \({^{\circ }}\)C. \(^{1}\)H NMR (400 MHz, \(\hbox {CDCl}_{3})\): \(\delta \) 1.12 (s, 6H, Me), 1.23 (s, 6H, Me), 2.19 (m, 4H, \(\hbox {CH}_{2})\), 2.35 (m, 4H, \(\hbox {CH}_{2})\), 5.49 (s, 1H, CH), 7.02 (d, \(J=7.6\) Hz, 2H, ArH), 7.23 (m, 2H, ArH), 11.89 (s, 1H, OH).\(^{ 13}\)C NMR (100 MHz, \(\hbox {CDCl}_{3})\): \(\delta \) 27.41, 29.68, 31.42, 32.40, 46.42, 47.04, 115.33, 128.19, 128.34, 129.77, 130.01, 131.58, 136.70, 189.43, 190.63.

2.4.3 2,2\(^{\prime }\)-((2-Nitrophenyl)methylene)bis(5,5-dimethylcyclohexane-1,3-dione) (9o)

M.p.: 204–206 \({^{\circ }}\)C. \(^{1}\)H NMR (400 MHz, \(\hbox {CDCl}_{3})\): \(\delta \) 1.02 (s, 6H, Me), 1.12 (s, 6H, Me), 2.26–2.35 (m, 4H, \(\hbox {CH}_{2})\), 2.43-2.54 (m, 4H, \(\hbox {CH}_{2})\), 6.05 (s, 1H, CH), 7.26 (s, 1H, ArH), 7.32 (m, 1H, ArH), 7.48 (d, \(J=7.6\) Hz, 1H, ArH), 7.51 (d, \(J=7.8\) Hz, 1H, ArH), 11.60 (s, 1H, OH).\(^{ 13}\)C NMR (100 MHz, \(\hbox {CDCl}_{3})\): \(\delta \) 28.14, 28.63, 30.06, 31.90, 46.31, 46.84, 114.64, 124.33, 127.17, 129.57, 131.36, 132.10, 149.73, 189.41, 191.20.
Table 2

Optimization of the reaction condition in the synthesis of compound 3a.

Entry

Solvent

Temperature (\({^{\circ }}\)C)

Time (min)

Yield (%)

1

\(\hbox {H}_{{2}}\)O

25

30

trace

2

EtOH

25

30

50

3

\(\hbox {CH}_{{3}}\)CN

25

30

35

4

\(\hbox {CH}_{{2}}\hbox {Cl}_{{2}}\)

25

30

32

5

THF

25

30

44

6

Neat

25

30

95 \(^\mathrm{a}\)

7

Neat

50

15

90

8

Neat

90

15

50

\(^\mathrm{a}\) The best condition

Table 3

Optimization of the amount of \(\hbox {SiO}_{{2}}\) NPs as a catalyst in the synthesis of compound 3a.

Entry

Catalyst (mol%)

Time (min)

Yield (%)

1

-

60

trace

2

1

60

75

3

2

30

95 \(^\mathrm{a}\)

4

5

25

95

5

10

20

95

\(^\mathrm{a}\) The best condition

Scheme 1

A plausible mechanism for the synthesis of 2,3-dihydro-1H-perimidine derivatives.

3 Results and Discussion

3.1 SiO \(_{2}\) NPs as an efficient catalyst to improve the synthetic procedure of 2,3-dihydro-1H-perimidines

We wish to report our results in the synthesis of 2,3-dihydro-1H-perimidines (3a3p) by the reaction of 1,8-diaminonaphthalene 1 and various aldehydes 2 using \(\hbox {SiO}_{{2}}\) as a nano heterogeneous catalyst (Table 1). To study the effect of solvent and temperature in the reaction of benzaldehyde and 1,8-diaminonaphthalene was chosen as a model reaction (Table 2). Among the examined conditions, grinding in a neat condition at 25 \({^{\circ }}\)C was found to be the most effective situation to produce excellent yields of products (entry 6). Also, in the optimization procedure, 2 mol% of catalyst was the appropriate amount of the reaction. Lesser amount gave a low yield and bigger amounts could not cause the obvious increase in the production of 3a (Table 3). Finally, the recovered catalyst could be reused without any noticeable loss in its reactivity. The new structures of products were characterized by spectral data (\(^{1}\)H NMR and \(^{13}\)C NMR). Other structures were characterized in comparison to their authentic samples.

Scheme 2

The Crucial role of catalyst in limiting the reaction to yield products 9.

A plausible mechanism and the crucial role of \(\hbox {SiO}_{{2}}\) NPs in activating the carbonyl group of the aldehyde is shown in Scheme 1. Aldehyde 2 and 1,8-diaminonaphthalene 1 was condensed by releasing one water molecule to form imine intermediate 6. After imine formation 6, it might be possible to interact with \(\hbox {SiO}_{{2}}\) nanoparticle by hydrogen bonding which has an intramolecular react with a second amine group to form intermediate 7. Finally, 1,3-proton transfer gives the corresponding 2,3-dihydro-1H-perimidines (3a3p).

3.2 SiO \(_{2}\) NPs as an efficient catalyst to improve the synthetic procedure of tetraketone derivatives

In continuation of our work, we examined \(\hbox {SiO}_{{2}}\) as a nano heterogeneous catalyst in the condensation of benzaldehydes 2 with 5,5-dimethyl-1,3-cyclohexanediones 8. As illustrated in Scheme 2, the crucial role of catalyst in limiting the reaction to yield products 9 or 10 is evident.[37] Surprisingly, only intermediate 2,2\(^\prime \)-phenylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1,3-dione) (9a) obtained in 92% yield and cyclized product 10 did not form.

Initially, the optimization of reaction condition was studied in a model reaction of benzaldehyde and dimedone in preparing compound 9a (Table 4). It was found that solvent-free condition can afford the product in good yield even better than other organic solvents (Entries 1–5). In addition, it was found that increasing the temperature to 110 \({^{\circ }}\)C leads to the higher yields (Entries 6 and 7). Entry 7 was the most desired condition among the various reaction conditions used in Table 1. In addition, in the optimization procedure, 2 mol% of catalyst was the appropriate amount for the reaction as shown in Table 5. The fewer amount gave a low yield and the more amounts could not cause the apparent increase in the production of 2,2\(^\prime \)-phenylmethylenebis(5,5-dimethyl-2-cyclohexene-1,3-dione) (9a). Therefore, a mixture of dimedones, various benzaldehydes bearing electron-withdrawing and electron-donating substituents and \(\hbox {SiO}_{{2}}\) NPs as a catalyst were heated at 110 \({^{\circ }}\)C under solvent-free condition to prepare crude products 2,2\(^\prime \)-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1,3-diones) (9a9p) in high to excellent yields (Table 6). The resulting solid products were dissolved in hot ethanol to crystallize; then were characterized by \(^{1}\)H NMR and \(^{13}\)C NMR analysis and by comparison with their authentic samples.
Table 4

Optimization of the reaction condition in the synthesis of compound 9a.

Entry

Solvent

Temperature (\({^{\circ }}\)C)

Time (h)

Yield (%)

1

\(\hbox {H}_{{2}}\)O

70

1

30

2

EtOH

70

1

35

3

Toluene

70

1

50

4

THF

70

1

47

5

Neat

70

1

62

6

Neat

90

30 min

80

7

Neat

110

15 min

92 \(^\mathrm{a}\)

\(^\mathrm{a}\) The best condition

Table 5

Optimization of the amount of nano-\(\hbox {SiO}_{{2}}\) as a catalyst in the synthesis of compound 9a.

Entry

Catalyst (mol%)

Time (min)

Yield (%)

1

-

60

trace

2

1

30

76

3

2

15

92 \(^\mathrm{a}\)

4

5

8

95

5

7

5

95

\(^\mathrm{a}\) The best condition

Table 6
Syntheses of tetraketone derivatives 9a9p catalyzed by \(\hbox {SiO}_{{2}}\) NPs.
Open image in new window

Entry

-X

R

Product

Time (min)

Yield (%)

M.p. (\({^{\circ }}\)C)

1

H

Me

9a

15

92

194-195 [32]

2

4-OH

Me

9b

30

74

187-189 [32]

3

4-Cl

Me

9c

15

95

136-138 [31]

4

4-\(\hbox {NO}_{{2}}\)

Me

9d

10

97

177-179 [31]

5

4-OMe

Me

9e

15

90

136-139 [31]

6

4-Me

Me

9f

20

92

123-126 [31]

7

H

H

9g

10

95

208-210 [31]

8

4-OH

H

9h

30

80

197-199[31]

9

4-Cl

H

9i

20

93

202-204 [31]

10

2-\(\hbox {NO}_{{2}}\)

H

9j

8

95

204-206 [32]

11

4-\(\hbox {NO}_{{2}}\)

H

9k

5

96

210-212 [32]

12

4-OMe

H

9l

20

90

190-191 [32]

13

3-Br

H

9m

10

96

206-208 [32]

14

4-Me

H

9n

15

92

190-191 [31]

15

2-\(\hbox {NO}_{{2}}\)

Me

9o

10

93

204-206 [32]

16

3-Br

H

9p

7

92

206-208 [31]

The mechanism seems to proceed via sequential Knoevenagel condensation-Michael addition reaction. The crucial role of \(\hbox {SiO}_{{2}}\) NPs is shown in Scheme 3 by forming a complex and thus activating the carbonyl group of benzaldehydes for nucleophilic addition. In this protocol, intermediate alcohol 11 is formed by the attack of activated dimedone 8. After the Knoevenagel condensation reaction, intermediate 12 which undergoes the nucleophilic attacking of another dimedone by Michael addition is transformed into the desired products (9a9p).

Scheme 3

Proposed mechanism for syntheses of tetraketone derivatives.

Fig. 1

SEM image of \(\hbox {SiO}_{{2}}\) NPs.

Table 7

Reusability of \(\hbox {SiO}_{{2}}\) NPs as catalyst.

 

Run

 

1

2

3

4

Yield of compound 3a

95%

93%

90%

88%

Yield of compound 9a

92%

91%

89%

86%

Table 8

Comparison of various catalysts in the synthesis of 2,3-dihydro-1H-perimidines in recent years.

Entry

Catalyst

Solvent

Condition

Time

Yield (%)

Year

1

NaY zeolite

Ethanol

Stir. at rt.

4550 h

70

2009 [36]

2

NSSA

Ethanol

Stir. at rt.

50 min

84

2010 [28]

3

CMK-5-\(\hbox {SO}_{{3}}\)H

Ethanol

Stir. at rt.

5 min

91

2013 [39]

4

\(\hbox {I}_{{2}}\)

Ethanol

Stir. at rt.

40 min

84

2013 [29]

Comparing the current work with previous works

5

SiO \(_{2}\) NPs

Neat

Grinding

10-60 min

85–97

This work

Table 9

Comparison of various conditions in the synthesis of tetraketones in recent years.

Entry

Catalyst

Solvent

Condition

Time

Yield (%)

Ref.

1

-

DMF

Stir. at 80 \({^{\circ }}\)C

1 h

6586

2000 [30]

2

Yb(OTf)\(_{3}\)-\(\hbox {SiO}_{{2}}\)

Neat

Grinding

2–5 min

7388

2011 [31]

3

-

\(\hbox {H}_{{2}}\)O

Stir. at rt.

14 h

6499

2010 [32]

Comparing the current work with previous works

4

SiO \(_{2}\) NPs

Neat

Heating at 110 \({^{\circ }}\) C

5–30 min

74–97

This work

3.3 Catalyst

Moreover, mesoscopic structure of silica with 50 nm particles is established in the SEM image (Figure 1) of these nanoparticles which were prepared according to the literature.[38]

To check the reusability, the recovered catalyst could be washed with diluted aqueous \(\hbox {Et}_{{3}}\)N solution, water and acetone sequentially. After a period of drying, the catalyst could be reused in the synthesis of compound 9a and 3a as a model reaction. The process of recycling was completed four times without any noticeable loss of reactivity (Table 7).

We have compared the efficiency of \(\hbox {SiO}_{{2}}\) NPs with various conditions in the synthesis of 2,3-dihydro-1H-perimidines as shown in Table 8. In addition, we have also compared the efficiency of various catalysts in the synthesis of tetraketones (Table 9). The high yield of products and short reaction times demonstrated that \(\hbox {SiO}_{{2}}\) NPs acts as an efficient catalyst in these reactions.

4 Conclusions

In conclusion, we have developed a simple strategy for the synthesis of a series of organic compounds using the catalytic amount of \(\hbox {SiO}_{{2}}\) nanoparticles under mild condition. The advantages of this method are solvent-free conditions, broad scope, easy handling, and high to excellent yields. Further, some different selectivities of \(\hbox {SiO}_{{2}}\) NPs catalytic system is observed which is the formation of 2,2\(^\prime \)-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) and not its corresponding cyclized compound.

Notes

Acknowledgements

We gratefully acknowledge the financial support from the Research Council of the University of Mazandaran.

Supplementary material

12039_2019_1607_MOESM1_ESM.pdf (1.9 mb)
Supplementary material 1 (pdf 1929 KB)

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Copyright information

© Indian Academy of Sciences 2019

Authors and Affiliations

  • Heshmatollah Alinezhad
    • 1
    Email author
  • Armin Ahmadi
    • 1
  • Parvin Hajiabbasi
    • 1
  1. 1.Department of Organic Chemistry, Faculty of ChemistryUniversity of MazandaranBabolsarIran

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