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Communication

An Efficient One-Pot Three-Component Synthesis of Fused 1,4-Dihydropyridines Using HY-Zeolit

by
Mohammad Nikpassand
,
Manouchehr Mamaghani
* and
Khalil Tabatabaeian
Department of Chemistry, Faculty of Sciences, University of Guilan, P. O. Box 41335-1914, Rasht, Iran
*
Author to whom correspondence should be addressed.
Molecules 2009, 14(4), 1468-1474; https://doi.org/10.3390/molecules14041468
Submission received: 6 March 2009 / Revised: 19 March 2009 / Accepted: 30 March 2009 / Published: 8 April 2009
Browse Figure
Versions Notes

Abstract

:
A facile and convenient protocol was developed for the fast (2.5-3.5 h) and high yielding (70-90 %) synthesis of fused 1,4-dihydropyridines from dimedone in the presence of HY-zeolite as an efficient recyclable heterogeneous catalyst.

1. Introduction

1,4-Dihydropyridines represent an important class of compounds which are found in many biologically active products, such as vasodilator, bronchodilator, anti-atherosclerotic, antitumor, geroprotective, hepatoprotective and antidiabetic agents [1]. Numerous synthetic methods have been reported for the preparation of 1,4-dihydropyridine derivatives under classical or modified conditions [2,3,4,5,6,7,8,9,10]. However, some of these methods suffer from long reaction times, low yields, use of large quantities of volatile organic solvents, harsh reaction conditions and tedious workups, therefore, development of an efficient and versatile method is still required.
HY-zeolite is unique acid heterogeneous catalyst that has become popular over the last two decades. It is used in various chemical transformations, such as liquid phase acylation of amines [11], direct conversion of aldehydes into amines [12], selective removal of N-Boc protecting groups from aromatic amines [13], one-pot synthesis of 2,3-dihydro-2,2-dimethylbenzofurans [14], and one-pot syntheses of polyhydroquinolines [15].
This remarkable catalytic activity together with easy availability, operational simplicity and recoverability of HY-zeolite encouraged us to utilize this catalyst for the synthesis of fused 1,4-dihydropyridine derivatives.

2. Results and Discussion

Recent developments in 1,4-dihydropyridine chemistry and our continued interest in the development of efficient and environmentally friendly procedures for the synthesis of heterocyclic compounds [16,17,18,19,20,21,22,23], prompted us to study the conversion of dimedone into fused 1,4-dihydropyridines in the presence of HY zeolite (Si/Al: 2.54). The reaction of dimedone (1, 2 eq.) with 1 equiv. of each of various arylaldehydes 2a-i and NH4OAc in EtOH in the presence of HY-zeolite furnished the desired fused 1,4-dihydropyridine derivatives 3a-i (Scheme 1) in reasonable reaction times (2.5-3.5 h) and high yields (70-90%) (Table 1). Moreover, the catalyst was easily recovered and the high catalytic activity was maintained even after third reuse of the catalyst.
Molecules 14 01468 g001 550
Scheme 1. Synthesis of 1,4-dihydropyridines from dimedone in the presence of HY-zeolite.
Scheme 1. Synthesis of 1,4-dihydropyridines from dimedone in the presence of HY-zeolite.
Molecules 14 01468 g001
The reaction, using substrate 2a, was also performed in the presence of CH3CO2H (1 mL/mmol substrate, 5 h, 67%), ZnCl2 (0.01 g/mmol substrate, 6 h, 65%) and RuCl3 (0.01 g/mmol substrate, 5.5 h, 70%) under optimized condition, which furnished the desired product after longer reaction times and in lower yields. The control reaction was carried out on the substrates 2a and 2d in refluxing ethanol without the zeolite catalyst. Under this classical condition the reaction proceeded smoothly resulting in the expected 1,4-dihydropyridine products after longer reaction times and in lower yields (2a: 6.5 h, 65%; 2d: 8.0 h, 63%). These results revealed that using HY-zeolite as catalyst appreciably shortens the reaction times and increases the product yields. All of the products were fully characterized by spectroscopic methods (IR, 1H-NMR, 13C-NMR) and elemental analysis.
Table
Table 1. Synthesis of fused 1,4-dihydropyridine derivatives (3a-i) using HY-zeolite.
Table 1. Synthesis of fused 1,4-dihydropyridine derivatives (3a-i) using HY-zeolite.
EntryAldehydeTime (h)Yield (%)1,2
a2-NO2 C6H4CHO 2.5 (6.5)3 75 (65)3
b3-NO2 C6H4CHO2.583
c4-NO2 C6H4CHO3.079
d2-ClC6H4CHO3.5 (8.0)375 (63)3
e4-ClC6H4CHO3.577
f3-BrC6H4CHO3.090
g4-FC6H4CHO3.570
h Molecules 14 01468 i0013.582
i Molecules 14 01468 i0023.578
1 Isolated yields; 2 All the products were Identified by spectroscopic (IR, 1H-NMR, 13C- NMR) and elemental analyses. 3A mixture of dimedone (20 mmol), aryl aldehydes (2a, 2d) (10 mmol) and NH4OAc (10 mmol) in EtOH (10 mL) was refluxed for the required reaction time, after which removal of the solvent produced the desired products 3a and 3d in 65% and 63% yields, respectively.

Conclusions

In summary, we report a simple protocol for the synthesis of fused 1,4-dihydropyridines using HY zeolite as an efficient catalyst. The simplicity, easy workup, together with the use of inexpensive, environmentally friendly and reusabile catalyst, are the notable features of this catalytic procedure.

3. Experimental

3.1. General

Melting points were measured on an Electrothermal 9100 apparatus. IR spectra were determined on a Shimadzo IR-470 spectrometer. 1H-NMR and 13C-NMR spectra were recorded on a 500 MHz Bruker DRX-500 in CDCl3 as solvent and with TMS as internal standard. Chemicals were purchased from Merck and Fluka. Elemental analyses were done on a Carlo-Erba EA1110CNNO-S analyzer and agreed with the calculated values. All solvents used were dried and distilled according to standard procedures.

3.2. General procedure for the synthesis of 3a-i in the presence of HY-zeolite

A mixture of dimedone (20 mmol), aryl aldehydes (10 mmol), NH4OAc (10 mmol), HY-zeolite (0.1 g) in EtOH (10 mL) was refluxed for the required reaction time (Table 1). The progress of the reaction was monitored by TLC (EtOAc: petroleum ether 3:1). After completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated under vacuum and the residue was recrystallized from ethanol to produce 1,4-dihydropyridine derivatives 3a-i as pure crystalline products in 70-90% yields.
3,3,6,6-Tetramethyl-9-(2-nitrophenyl)-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione (3a): Brown solid, mp 281-282 oC; 1H-NMR δ 0.96 (s, 6H), 1.06 (s, 6H), 2.23- 2.46 (m, 8H), 5.80 (s, 1H), 7.21 (t, J = 6.99 Hz, 1H), 7.30- 7.35 (d, J = 6.81 Hz, 1H), 7.41- 7.48 (m, 2H); 13C-NMR δ 27.8, 29.5, 32.9, 41.2, 51.1, 112.9, 124.5, 127.0, 132.5, 134.2, 141.2, 149.6, 149.8, 195.9; IR (neat, cm-1) 3450, 3080, 2980,1650, 1520, 1480, 1360, 1220, 1140. Anal. Calcd. for C23H26N2O4: C, 70.03; H, 6.63; N, 7.10. Found: C, 70.25; H, 6.48; N, 7.02.
3,3,6,6-Tetramethyl-9-(3-nitrophenyl)-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione (3b): Off white solid, mp 273-275 oC; 1H-NMR δ 0.86 (s, 6H), 1.01 (s, 6H), 2.0 (d, J = 16.3 Hz , 2H ), 2.10 (d, J = 16.3 Hz , 2H), 2.28 (d, J = 17.1 Hz, 2H), 2.35 (d, J = 17.1 Hz, 2H), 5.01 (s, 1H), 7.29 (t, J = 7.86 Hz, 1H), 7.65 (d, J = 6.9 Hz, 1H), 7.83 (d, J = 8.1 Hz, 1H), 8.02 (s, 1H), 8.90 (s, br., 1H) ; 13C-NMR δ 27.4, 29.9, 32.9, 34.4, 51.1, 112.2, 121.2, 123.1, 130.0, 135.2, 148.4, 149.6, 150.2, 195.6; IR (neat, cm-1) 3380, 3060, 2960, 1645, 1610, 1520, 1480, 1360, 1340, 1220, 1140. Anal. Calcd. for C23H26N2O4: C, 70.03; H, 6.63; N, 7.10. Found: C, 69.88; H, 6.52; N, 7.28.
3,3,6,6-Tetramethyl-9-(4-nitrophenyl)-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione (3c): Yellow-orange solid, mp 282-283 oC; 1H-NMR δ 0.87 (s, 6H), 1.02 (s, 6H), 2.04 (d, J = 16.3 Hz, 2H), 2.15 (d, J = 16.3 Hz, 2H), 2.26 (d, J = 17.0 Hz, 2H), 2.34 (d, J = 17.0 Hz, 2H), 5.05 (s, 1H), 7.44 (d, J = 8.5 Hz, 2H), 7.98 (d, J = 6.9 Hz, 2H), 8.49 (s, 1H); 13C-NMR δ 27.4, 29.9, 32.9, 34.9, 51.0, 112.3, 123.5, 129.4, 146.3, 149.8, 154.9, 195.6; IR (neat, cm-1) 3384, 3070, 2956,1643, 1515, 1479, 1342, 1218, 1166. Anal. Calcd. for C23H26N2O4: C, 70.03; H, 6.63; N, 7.10. (Found: C, 69.93; H, 6.75; N, 7.32.
9-(2-Chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione (3d): Off white solid, mp 217-219 oC; 1H-NMR δ 1.05 (s, 6H), 1.14 (s, 6H), 2.10-2.30 (m, 4H), 2.45-2.62 (m, 4H), 5.04 (s, 1H), 7.09 (t, J= 7.2 Hz, 1H), 7.01-7.19 (m, 1H), 7.25 (d, J = 7.5 Hz, 1H), 7.47 (d, J = 6.4 Hz, 1H); 13C-NMR δ 27.8, 29.7, 32.5, 41.2, 51.2, 114.2, 126.8, 127.6, 128.2, 130.6, 133.9, 149.4, 163.5, 197.0; IR (neat, cm-1) 3400, 2980,1660, 1620, 1465, 1350, 1200. Anal. Calcd. for C23H26ClNO2: C, 71.96; H, 6.82; N, 3.65. Found: C, 71.72; H, 6.55; N, 3.81.
9-(4-Chlorophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione (3e): Off white solid, mp 228-229 oC; 1H-NMR δ 1.03 (s, 6H), 1.15 (s, 6H), 2.17- 3.33 (m, 8H), 5.51 (s, 1H), 7.20 (d, J = 8.3 Hz, 2H), 7.32 (d, J = 8.3 Hz, 2H), 8.06 (s, 1H); 13C-NMR δ 27.5, 30.0, 33.0, 41.1, 51.2, 113.3, 128.5, 129.9, 132.0, 145.6, 149.7, 196.8; IR (neat, cm-1) 3429, 3178, 3060, 2958,1641,1606, 1488, 1222, 1143. Anal. Calcd. for C23H26ClNO2 : C, 71.96; H, 6.82; N, 3.65. Found: C, 71.83; H, 6.71; N, 3.55.
9-(3-Bromophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione (3f): Off white solid, mp 305-307 oC; 1H-NMR δ 1.01 (s, 6H), 1.12 (s, 6H), 2.18-2.35 (m, 8H), 5.05 (s, 1H), 7.11 (t, J = 7.74 Hz, 1H), 7.25 (d, J = 7.73 Hz, 1H), 7.35 (t, J = 7.59 Hz, 1H), 7.48 (s, 1H), 7.98 (s, 1H); 13C-NMR δ 27.5, 30.0, 33.1, 41.1, 51.3, 113.1, 122.6, 127.5, 129.5, 130.0, 131.4, 149.3, 149.8, 196.3; IR (neat, cm-1) 3280, 3080, 2970, 1640, 1555, 1250, 1220. Anal. Calcd. for C23H26BrNO2: C, 64.49; H, 6.11; N, 3.27. Found: C, 64.66; H, 6.32; N, 3.11.
9-(4-Fluorophenyl)-3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione (3g): Yellow solid, mp 215-218 oC; 1H-NMR δ 0.98 (s, 6H), 1.10 (s, 6H), 2.04- 2.38 (m, 8H), 5.09 (s, 1H), 6.90 (m, 2H), 7.30 (m, 2H), 8.30 (s, 1H); 13C-NMR δ 27.4, 30.0, 33.0, 41.0, 51.3, 113.3, 115.2, 129.7, 143.0, 149.9, 162.5, 196.5 ; IR (neat, cm-1) 3355, 3047, 2958, 1618, 1498, 1362, 1220, 1147. Anal. Calcd. for C23H26FNO2: C, 75.18; H, 7.12; N, 3.81. Found: C, 75.32; H, 7.23; N, 3.67.
3,3,6,6-tetramethyl-9-(2-(6-(2-(3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine1,8(2H,5H,9H,10H)-dione-9-yl)hexoxy)phenoxy)phenyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione (3h): Off white solid, mp 275-277 oC; 1H-NMR δ 0.90 (s, 12H), 0.97 (s, 12H), 1.01-1.06 (m, 4H), 1.96-2.29 (m, 20H), 3.97 (s, br., 4H), 5.30 (s, 2H), 6.71-7.26 (m, 8H), 8.83 (s, 2H); IR (neat, cm-1) 3290, 3065, 2960, 1645, 1490, 1365, 1225, 745. Anal. Calcd. for C52H64N2O6: C, 76.81; H, 7.93; N, 3.45. Found: C, 76.95; H, 7.82; N, 3.59.
3,3,6,6-tetramethyl-9-(2-(4-(2-(3,3,6,6-tetramethyl-3,4,6,7-tetrahydroacridine1,8(2H,5H,9H,10H)-dione-9-yl)butoxy)phenoxy)phenyl-3,4,6,7-tetrahydroacridine-1,8(2H,5H,9H,10H)-dione (3i): Off white solid, mp 269-271 oC; 1H-NMR δ 0.92 (s, 12H), 1.04 (s, 12H), 1.98-2.35 (m, 20H), 4.06 (s, br., 4H), 5.22 (s, 2H), 6.80-7.06 (m, 8H), 8.67 (s, 2H); IR (neat, cm-1) 3290, 3060, 2960, 1660, 1480, 1360, 1235, 745. Anal. Calcd. for C50H60N2O6: C, 76.50; H, 7.70; N, 3.57. Found: C, 76.38; H, 7.78; N, 3.60.

Acknowledgements

Financial support from the Research Council of University of Guilan is sincerely acknowledged. We also thank Prof. M.A. Zanjanchi for the HY-Zeolite and Dr. N.O. Mahmoodi for the aryl aldehydes 2h and 2i.

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  • Sample Availability: Samples of the compounds 3a-i are available from the authors.

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MDPI and ACS Style

Nikpassand, M.; Mamaghani, M.; Tabatabaeian, K. An Efficient One-Pot Three-Component Synthesis of Fused 1,4-Dihydropyridines Using HY-Zeolit. Molecules 2009, 14, 1468-1474. https://doi.org/10.3390/molecules14041468

AMA Style

Nikpassand M, Mamaghani M, Tabatabaeian K. An Efficient One-Pot Three-Component Synthesis of Fused 1,4-Dihydropyridines Using HY-Zeolit. Molecules. 2009; 14(4):1468-1474. https://doi.org/10.3390/molecules14041468

Chicago/Turabian Style

Nikpassand, Mohammad, Manouchehr Mamaghani, and Khalil Tabatabaeian. 2009. "An Efficient One-Pot Three-Component Synthesis of Fused 1,4-Dihydropyridines Using HY-Zeolit" Molecules 14, no. 4: 1468-1474. https://doi.org/10.3390/molecules14041468

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