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Original Article
8 (
1
); 138-141
doi:
10.1016/j.arabjc.2011.01.027

Ionic liquid[tbmim]Cl2/AlCl3 under ultrasonic irradiation towards synthesis of 1,4-DHP’s

, ,
 Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632014, India

*Corresponding author. Tel.: +91 4162202332 kvpsvijayakumar@gmail.com (V. Vijayakumar)

Received: , Accepted: ,
© The Author(s) 2011
Disclaimer:
This article was originally published by Elsevier and was migrated to Scientific Scholar after the change of Publisher.

Peer review under responsibility of King Saud University.

Available online 1 February 2011

Abstract

One pot, three-component synthesis of 1,4-dihydropyridines using ionic liquid 3,3′-thionyl-bis-1,1′-methylimidazolium chloroaluminate ([tbmim]Cl2/AlCl3) was found to be efficient to afford good to excellent yields at room temperature under ultrasonic irradiation. This method has many advantages, which avoids the use of harmful catalysts, occurence of reactions at room temperature, high yields and methodological simplicity.

Keywords

1,4-DHP’s
[tbmim]Cl2/AlCl3
Hantzsch reaction
Ultrasound irradiation
1

1 Introduction

It is well known that Hantzsch 1,4-dihydropyridines (1,4-DHP’s) exhibit a wide range of biological properties (Mauzeral and Wertheimer, 1955), acting as potent vasodilators, antihypertensives, bronchodilators, heptaprotective, antitumor, antimutagenic, geroprotective and antidiabetic agents (Di Stilo et al., 1998). Moreover a number of DHP’s acts as calcium antagonists (Janis and Triggle, 1983; Bocker and Guengerich, 1986; Gordeev et al., 1996) and they have been introduced for the treatment of congestive heart failure. In addition to this 1,4-DHP’s exhibit several other medicinal applications like neuroprotectant (Klusa, 1995), platet anti-aggregator activity (Bretzel et al., 1993), as cerebral antiischemic agents in the treatment of Alzheimer’s disease (Bretzel et al., 1992) and as a chemosensitizer in tumor therapy (Boer and Gekeler, 1995).

1,4-DHP’s are generally synthesized using Hantzsch method (Hantzsch, 1882), which involves one pot cyclocondensation of aldehydes, dicarbonyls/β-ketoesters and ammonium acetate/ammonia/primary amine either in refluxing with acetic acid or alcohol leading to low yields with longer reaction time (Loev and Snader, 1965; Sausins and Duburs, 1988). Recently, a number of modified methods have been developed (Evdokimor et al., 2006). Other procedures comprise the use of microwaves (Khadikar et al., 1995), ionic liquids (Ji et al., 2004), high temperatures at reflux (Phillips, 1949), TMSCl–NaI (Sabitha et al., 2003), InCl3 (Babu and Perumal, 2000), I2 (Ko et al., 2005), SiO2/NaHSO4 (Adharvana and Syamasundar, 2005), SiO2/HClO4 (Maheswara et al., 2006), CAN (Ko and Yao, 2006), Na- and Cs-Norit carbons (Perozo-Rondon et al., 2006), tetrabutylammonium hydrogen sulfate (Tewari et al., 2004), fermenting Baker’s yeast (Lee, 2005), organocatalysts (Kumar and Maurya, 2007) and metal triflates (Wang et al., 2005). All the above methods are how ever associated with several draw backs, such as unsatisfactory yields, longer duration, difficulty in handling of reagents, toxic solvents, hence the development of an efficient synthesis of Hantzsch 1,4-dihydropyridines seemed to be of prime importance. In green synthesis ionic liquids play a major role. Initially ionic liquids are introduced as alternative green reaction media because of their unique chemical and physical properties of non-volatility, non-flammability, thermal stability, and controlled miscibility. But nowadays ionic liquids have proved to be useful beyond this, showing their importance in controlling reactions as catalysts (Jain et al., 2005).

In organic synthesis ultrasound irradiation has been considered as a clean and useful protocol, compared with the traditional methods. A large number of organic reactions can be carried out in higher yields, shorter reaction time or milder conditions in ultrasonic irradiation (Wilkes, 2002). In continuation of earlier interest on 1,4-DHP’s (Rathore et al., 2009; Palakshi Reddy et al., 2009, 2010; Thenmozhi et al., 2009; Fun et al., 2009a,b,c) herein we report an efficient and simple procedure for the synthesis of 1,4-DHP derivatives at room temperature under ultrasonication using ionic liquid[tbmim]Cl2/AlCl3 as catalyst (see Scheme 1).

Scheme 1

2

2 Experimental

The melting points were recorded in open capillaries and corrected with benzoic acid. Thin-layer chromatography (TLC) was carried out to monitor the course of the reaction and purity of the product. IR spectra recorded in an Avatar-330 FTIR spectrophotometer (Thermo Nicolet), and only noteworthy absorption levels (reciprocal centimeters) were listed. 1H NMR spectra were recorded on Bruker AMX 400-MHz or 300-MHz spectrometer using CDCl3 or DMSO as solvent and TMS as internal standard. Mass spectra were recorded on a LC-MS. Ionic liquid[tbmim]Cl2/AlCl3 was prepared according to the literature (Ling et al., 2006).

2.1

2.1 General procedure for the synthesis of 1,4-DHP’s

A mixture of aromatic aldehyde 1 (1 mmol), ethylacecoacetate/acetylacetone 2 (2 mmol) and ammonium acetate 3 (1 mmol), was taken in a round bottomed flask mixed with[tbmim]Cl2/AlCl3 (0.5 mmol), which was irradiated under ultrasonic waves at room temperature for an appropriate time as indicated in Table 2. The progress of the reaction was monitored by TLC. The reaction mixture was then extracted with chloroform (10 mL) leaving behind[tbmim]Cl2/AlCl3. The organic layer was then washed with water and dried over anhydrous Na2SO4. Organic solvent was evaporated under reduced pressure and a solid compound was crystallized from absolute ethanol to afford the pure corresponding 1,4-dihydropyridine derivatives 4(a–u) in excellent yields.

Table 2 Synthesis of various substituted 1,4-dihydropyridines using ionic liquid.
S. No Ph R US (min) Yield (%) M.P (°C)
4a C6H5 OC2H5 40 94 158–160
4b 4-ClC6H4 OC2H5 45 95 145–146
4c 4-OCH3C6H4 OC2H5 50 93 153–155
4d 3-NO2C6H4 OC2H5 30 96 165–167
4e 4-Pyridyl OC2H5 45 91 185–187
4f 3-Pyridyl OC2H5 50 90 188–190
4g 4-BrC6H4 OC2H5 45 93 148–150
4h 2-Thienyl OC2H5 50 90 172–173
4i 4-CH3C6H4 OC2H5 60 88 142–145
4j 4-HOC6H4 OC2H5 60 90 227–229
4k 3-HOC6H4 OC2H5 55 87 172–175
4l 3-NO2C6H4 CH3 35 94 180–182
4m 2-NO2C6H4 CH3 35 93 195–197
4n 2-Furyl CH3 50 90 169–170
4o 2-Thienyl CH3 55 91 170–172
4p 3-Pyridyl CH3 50 89 262–263
4q 3-ClC6H4 CH3 40 92 222–224
4r 3-OCH3C6H4 CH3 50 88 203–205
4s 4-C2H5C6H4 CH3 55 87 179–181
4t 4-Pyridyl CH3 50 89 245–246
4u 4-BrC6H4 CH3 40 93 109–111

Reaction conditions: aldehyde (10 mmol), ethylaceto acetate/acetylacetone (20 mmol), ammonium acetate (10 mmol), ionic liquid (0.5 mmol).

3

3 Results and discussion

Herein, we report a developed a methodology for the synthesis of 1,4-dihydropyridines (1,4-DHP’s) in the presence of[tbmim]Cl2/AlCl3 under ultrasound-irradiation. Herein we have carried out the reaction of benzaldehyde 1, ethylacetoacetate/acetylacetone 2 and ammonium acetate 3 catalyzed by[tbmim]Cl2/AlCl3. Different reaction conditions have been studied for optimization (Table 1).

Table 1 Optimization of reaction conditions for the synthesis of 1,4-DHP’s.
Entry Method Catalyst[tbmim]Cl2/AlCl3 Time (min) Yield (%)
1 Sonication 1 mmol 40 94
2 Sonication 0 mmol 40 70
3 Reflux 0 mmol 180 80
4 Reflux 0.5 mmol 90 89
5 Stirring 0.5 mmol 150 88
6 Sonication 0.5 mmol 40 94

Reaction conditions: benzaldehyde (10 mmol), ethylacetoacetate (20 mmol), ammonium acetate (10 mmol), ionic liquid.

The use of 1 mmol of ionic liquid does not affect the yield even after increase in reaction time. So 0.5 mmol of ionic liquid is sufficient to yield 1,4-DHP’s. It is important to note that in the absence of the ionic liquid and without using ultrasound irradiation, the yield of the reactions decreased with increase in time. Using ionic liquid as a promoter for the synthesis of Hantzsch 1,4-DHP’s does not only represent a dramatic improvement at room temperature with regard to yield (87–96%) over conventional thermal heating, but the reaction times are also considerably decreased compared to classical synthesis (3–6 h). Ultrasonic irradiation was very simple and convenient for the synthesis of 1,4-DHP’s in room temperature using ionic liquid in ultrasonic cleaner with a frequency of 40 kHz and a nominal power 100 W. In this experiment the ultrasonic technique represented a better procedure with respect to time and yield. After optimizing the conditions, the generality of this method was examined by the reaction of several substituted aldehydes, ethylaceto acetate/acetylacetone and ammonium acetate using[tbmim]Cl2/AlCl3 as a catalyst under ultrasound irradiation, the results are shown in Table 2.

Herein, we have found that the reactions of aromatic aldehydes having electron-withdrawing groups are fast as compared to the reaction of aldehydes having electron donating groups. Unlike those of ethylacetoacetate products, the reaction of acetylacetone products proceeded at lower rate less efficiently to give 1,4-DHP’s. The results obtained in the current method are illustrated in Table 2. All the products obtained were fully characterized by spectroscopic methods, such as IR, 1H NMR and mass spectroscopy and also by comparison with the reference compounds. Another advantage of the ionic liquid is that it is recyclable. In view of environmentally friendly methodologies, recovery and reuse of the ionic liquid is highly preferable.[tbmim]Cl2/AlCl3 is easily separated from reaction medium by washing with water and distillation of the solvent under vacuum and it can be reused for subsequent reactions. Recycled ionic liquid shows no loss of efficiency with regard to yield after four successive runs, hence this method can be regarded as a rapid, convenient and environmentally benign method for the synthesis of 1,4-dihydropyridine derivatives.

4

4 Conclusion

An efficient and environmentally friendly method has been developed for the synthesis of 1,4-dihydropyridines catalyzed by 0.5 mmol of[tbmim]Cl2/AlCl3 under ultrasonic irradiation. The use of sonication combining ionic liquid in the three-component condensation at room temperature brings up the merits like milder conditions, low pollution, good yields and simple work-up.

4.1

4.1 Spectral data for respective compounds

Compound 4a: IR (KBr) νmax 3348, 3052, 1692, 1633, 1223. 1H NMR (CDCl3, 400 MHz, ppm): δ 1.26 (t, 6H, J = 8 Hz), δ 2.35 (s, 6H), δ 4.10 (m, 4H, J = 4 Hz), δ 5.93 (s, 1H), δ 5.76 (s, 1H), δ 7.38–8.14 (Aromatic). MS: m/z 329 (M).

Compound 4b: IR (KBr) νmax 3345, 3091, 1705. 1H NMR (400 MHz, CDCl3): δ 1.22 (t, 6H, J = 6 Hz), δ 2.33 (s, 6H), δ 4.09 (m, 4H, J = 4 Hz), δ 4.96 (s, 1H), δ 5.70 (s, 1H), δ 7.17–7.25 (Aromatic). MS: m/z 363 (M), 364 (M+1).

Compound 4c: IR (KBr) νmax 3342, 3094, 1689. 1H NMR (400 MHz, CDCl3): δ 1.23 (t, 6H, J = 8 Hz), δ 2.34 (s, 6H), δ 3.72 (s, 3H), δ 4.09 (m, 4H, J = 4 Hz), δ 4.94 (s, 1H), δ 5.58 (s, 1H), δ 6.76–7.21 (Aromatic). MS: m/z 360 (M).

Compound 4d: IR (KBr) νmax 3357, 3092, 1692. 1H NMR (400 MHz, CDCl3): δ 1.23 (t, 6H, J = 8), δ 2.33 (s, 6H), δ 4.09 (m, 4H, J = 4 Hz), δ 5.90 (s, 1H), δ 5.73 (s, 1H), δ 7.38–8.14 (Aromatic). MS: m/z 374 (M).

Compound 4e: IR (KBr) νmax 3378, 3082, 1698. 1H NMR (400 MHz, CDCl3): δ 1.20 (t, 6H, J = 6 Hz), δ 2.30 (s, 6H), δ 4.10 (m, 4H, J = 4 Hz), δ 5.00 (s, 1H), δ 6.10 (s, 1H), δ 7.20–8.47 (Aromatic). MS: m/z 330 (M).

Compound 4f: IR (KBr) νmax 3378, 3082, 1698. 1H NMR (400 MHz, CDCl3): δ 1.20 (t, 6H, J = 6 Hz), δ 2.30 (s, 6H), δ 4.10 (m, 4H, J = 4 Hz), δ 5.00 (s, 1H), δ 6.10 (s, 1H), δ 7.20–8.60 (Aromatic). MS: m/z 330 (M).

Compound 4g: IR (KBr) νmax 3345, 3091, 1689. 1H NMR (400 MHz, CDCl3): δ 1.22 (t, 6H, J = 6 Hz), δ 2.33 (s, 6H), δ 4.09 (m, 4H, J = 4 Hz), δ 4.96 (s, 1H), δ 5.70 (s, 1H), δ 7.17–7.25 (Aromatic). MS: m/z 409 (M+2).

Compound 4n: IR (KBr) νmax 3342, 3094, 1689, 1638. 1H NMR (CDCl3, 400 MHz, ppm):δ 2.28 (s, 6H), δ 2.36 (s, 6H), δ 5.29 (s, 1H), δ 6.05 (s, 1H), δ 7.40–8.04 (Aromatic). MS: m/z 330 (M).

Compound 4o: IR (KBr) νmax 3342, 3094, 1689. 1H NMR (400 MHz, CDCl3): δ 2.28 (s, 6H), δ 2.38 (s, 6H), δ 5.29 (s, 1H), δ 6.10 (s, 1H), δ 7.40–8.10 (Aromatic). MS: m/z 314 (M).

Compound 4p: IR (KBr) νmax 3332, 3096, 1690. 1H NMR (400 MHz, CDCl3): δ 2.31 (s, 6H), δ 2.37 (s, 6H), δ 5.15 (s, 1H), δ 5.80 (s, 1H), δ 6.70–7.54 (Aromatic). 13C NMR (CDCl3): δ 20.0, 29.5, 4.7, 104.5, 141.4, 145.1, 157, 197.8. MS: m/z 259 (M+), 261 (M+2), 192.

Compound 4q: IR (KBr) νmax 3332, 3064, 1695. 1H NMR (400 MHz, CDCl3): δ 2.32 (s, 6H), δ 2.33 (s, 6H), δ 5.40 (s, 1H), δ 6.10 (s, 1H), δ 6.80–7.80 (Aromatic). 13C NMR (400 MHz, CDCl3): δ 20.6, 29.7, 35.0, 113.0, 123.7, 128.1, 135.1, 144.1, 150.0, 197.2. MS: m/z 274 (M−1), 275 (M), 276 (M+1).

Compound 4r: IR (KBr) νmax 3345, 3090, 1685. 1H NMR (400 MHz, CDCl3): δ 2.29 (s, 6H), δ 2.35 (s, 6H), δ 5.12 (s, 1H), δ 5.80 (s, 1H), δ 6.70–7.29 (Aromatic). 13C NMR (CDCl3, 400 MHz, ppm): δ 20.4, 30.0, 39.92, 113.7, 119.7, 142.8, 197.8. MS: m/z 299 (M).

Compound 4s: IR (KBr) νmax 3378, 3082, 1698, 963. 1H NMR (400 MHz, CDCl3): δ 2.34 (s, 6H), δ 2.20 (s, 6H), δ 5.11 (s, 1H), δ 5.81 (s, 1H), δ 7.16–7.26 (Aromatic). MS: m/z 303 (M), 304 (M+1).

Acknowledgment

We thank to Chemistry Division, VIT University, Vellore, India for providing facilities to carry research work.

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Appendix A

Supplementary data

Supplementary data associated with this article can be found, in the online version, at doi:10.1016/j.arabjc.2011.01.027.

Appendix A

Supplementary data

Supplementary material

Supplementary material Supplementary figures.


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