Startseite Aqueous heterogeneous synthesis of polysubstituted 2,6-dicyanoanilines via combined microwave and ultrasound-assisted multicomponent reaction
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Aqueous heterogeneous synthesis of polysubstituted 2,6-dicyanoanilines via combined microwave and ultrasound-assisted multicomponent reaction

  • Huangdi Feng

    Huangdi Feng received his PhD degree in applied chemistry from ECUST, with Prof. Gonghua Song. In 2010, he received a China Scholarship Council Scholarship and joined the group of Prof. Erik Van der Eycken, KU Leuven, Belgium, as a doctoral student; he received his PhD degree in chemistry in 2012. Currently, he is an assistant professor at the Chinese National Compound Library, Shanghai Institute of Materia Medica, Chinese Academy of Sciences. His research interests include the development of novel synthetic methodologies for biologically important compounds and medicinal chemistry.

         , Shengjie Lin

    Shengjie Lin was born in Zhejiang, China, in 1987. He graduated in Chemical Engineering and Technology in 2009 and is now a PhD student in Pesticide at ECUST under the supervision of Prof. Gonghua Song. His research interests focus on the design and application of novel microwave reactors.

         , Jiayi Wang

    Jiayi Wang was born in Hubei, China, in 1983. He graduated in Pharmaceutical Preparations in 2005 and received his PhD in Applied Chemistry in 2011 from ECUST under the supervision of Prof. Gonghua Song. Presently, he is a lecturer at the School of Pharmacy in ECUST. His research interests focus on the development of novel synthetic methodologies, pesticide design and synthesis.

         , Gonghua Song

    Gonghua Song is Professor of Chemical Engineering at the School of Pharmacy, East China University of Science and Technology (ECUST), Shanghai, China. He was born in 1962 and obtained his PhD from ECUST in 1991. In 1999, he was appointed as a full professor. His research interests are in green chemistry and agrochemicals.

     EMAIL logo     und Yanqing Peng

    Yanqing Peng is an Associate Professor in the Institute of Pesticides and Pharmaceuticals and Shanghai Key Laboratory of Chemical Biology at ECUST. His research program focuses on the development of new recoverable catalysts, novel routes to nanomaterials and ecofriendly agrochemicals. He has 45 internationally refereed journal papers on catalysis, green chemistry and material chemistry.
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Green Processing and Synthesis
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Abstract

A series of polysubstituted 3-aryl-2,6-dicyanoaniline derivatives were synthesized by one-pot multicomponent heterogeneous domino reaction of aromatic aldehyde, malononitrile and cyclic ketone under combined microwave and ultrasound irradiation in water. This facile approach reduces the reaction time and energy consumption and increases the yield and selectivity of the product.

Keywords: 2,6-dicyanoanilines; microwave; multicomponent reaction; ultrasound; water

1 Introduction

The development of high-throughput screening, domino processes and multicomponent reactions plays more and more important roles in modern synthetic organic che­mistry for the formation of carbon-carbon and carbon-heteroatom bonds [1–7]. Such efficient and atom-economic reactions are particularly useful for constructing highly complex molecules in a single procedural step, thus avoiding complicated purification operations and allowing savings in both solvents and reagents [8–11]. Activation of the organic reaction with microwave and ultrasound constitutes an important domain of modern organic chemistry [12–18]. This is mainly due to the fact that the power of microwave and ultrasound can reduce the reaction time, minimize energy consumption and increase the yield and selectivity of the product.

3-Aryl-2,6-dicyanoanilines with an amino group flanked by two cyano substituents not only occupy a unique place in various classes of organic compounds [19, 20] but also display interesting biological activities [21–23]. 2,6-Dicyanoanilines comprising one electron donor and two electron acceptors are typical acceptor-donor-acceptor (A-D-A) systems for the extensive study of photoinduced intramolecular electron transfer [24, 25]. The potential applications of these molecular systems, artificial photosynthetic systems [26], molecular electronic devices [27] and materials presenting semiconducting or nonlinear optical properties [28], were reported extensively. These compounds were reported to be prepared from malononitrile and α,β-unsaturated ketones, but the yields were very poor [29, 30]. The reaction between arylidenemalonodinitriles and 1-arylethylidenemalonodinitriles could also give 2,6-dicyanoanilines in the presence of base [31, 32]. Wang et al. developed the microwave-assisted one-pot synthesis of polysubstituted 3-aryl-2,6-dicyanoanilines from aldehydes, ketones and malononitrile. However, the yields of products were in the range of 50–63%, and only a few products from cycloketones have been reported [33]. In addition, most of the above-mentioned reactions were performed in organic solvent or in the presence of surfactant. Due to the environmental and economic concerns, water as a green reaction medium alternative to organic solvents has attracted more and more attention [34–36].

2 Experimental

2.1 General information

All solvents and reagents were purchased from commercial sources and were used without prior purification. All combined microwave and ultrasound irradiation (CMUI) experiments were carried out in a professional TCMC-102 microwave apparatus (Nanjing Lingjiang Technological Development Company, China) operating at a frequency of 2.45 GHz with continuous irradiation power from 0 to 500 W and an FS-250 professional ultrasound apparatus (Shanghai S. X. Ultrasonics, China) operating at a frequency of 20 KHz with controllable irradiation power from 10 to 100 W. The reactions were carried out in a 15-ml two-necked Pyrex flask, placed in the microwave cavity with the tip of the detachable horn immersed just under the liquid surface. The reaction mixture was irradiated at reflux condition using microwave (100 W) and ultrasound (50 W). Thin-layer chromatography (TLC) analysis was performed on aluminum-backed plates (SIL G/UV254). The products were purified by filtration or silica gel (200–300 mesh) column chromatography and were identified by 1H nuclear magnetic resonance (NMR) (CDCl3, 400 MHz) and gas chromatography-mass spectrometry (GC-MS). All the new products were identified by 1H and 13C NMR (CDCl3, 400 MHz) and high-resolution mass spectroscopy (EI).

2.2 General procedure for preparation of 3-aryl-2,6-dicyanoanilines

A mixture of aromatic aldehyde (2.0 mmol), cyclic ketone (2.0 mmol), malononitrile (4.4 mmol), NaOH (3.0 mmol) and water (5.0 ml) was subjected to CMUI (microwave: 100 W; ultrasound: 50 W) until nearly complete conversion of aromatic aldehyde as monitored by TLC. The crude product was collected by filtration and purified by recrystallization from ethanol or column chromatography on silica gel with 1:5 ethyl acetate/petroleum (v/v). All of the products were identified by 1H NMR (CDCl3, 400 MHz), 13C NMR, high resolution MS (HRMS) or GC-MS.

2.3 5-Amino-7-(4-fluorophenyl)-2,3-dihydro-1H-indene-4,6-dicarbonitrile (4b)

1H NMR (400 MHz, CDCl3): δ=7.36–7.39 (m, 2H), 7.19 (t, J=8.6 Hz, 2H), 5.10 (s, 2H), 3.13 (t, J=7.6 Hz, H), 2.72 (t, J=7.4 Hz, 2H), 2.08–2.15 (m, 2H); 13C NMR (100 MHz, CDCl3): δ=164.3, 161.8, 154.9, 151.3, 145.0, 133.1, 132.5, 130.4, 116.0, 115.2, 95.3, 93.4, 34.0, 31.9, 24.7; HRMS (EI): calcd for C17H12FN3 (M+) 277.1015, found 277.1017.

2.4 5-Amino-7-(3-bromophenyl)-2,3-dihydro-1H-indene-4,6-dicarbonitrile (4c)

1H NMR (400 MHz, CDCl3): δ=7.60 (d, J=7.6 Hz, 1H), 7.28–7.40 (m, 3H), 5.15 (s, 2H), 3.13 (t, J=7.6 Hz, 2H), 2.73 (t, J=7.4 Hz, 2H), 2.08–2.15 (m, 2H); 13C NMR (100 MHz, CDCl3): δ=115.0, 151.4, 144.2, 138.5, 133.0, 132.2, 131.3, 130.3, 127.1, 122.7, 95.1, 93.7, 34.0, 31.8, 24.7; HRMS (EI): calcd for C17H12BrN3 (M+) 337.0215, found 337.0209.

2.5 5-Amino-7-(benzo[d][1,3]dioxol-5-yl)-2,3-dihydro-1H-indene-4,6-dicarbonitrile (4g)

1H NMR (400 MHz, CDCl3): δ=6.84–6.97 (m, 3H), 5.09 (s, 2H), 3.12 (t, J=7.6 Hz, 2H), 2.76 (t, J=7.4 Hz, 2H), 2.07–2.14 (m, 2H); 13C NMR (100 MHz, CDCl3): δ=154.7, 151.4, 148.3, 147.8, 145.7, 133.1, 130.2, 122.6, 116.4, 108.9, 101.5, 95.4, 93.0, 34.0, 32.0, 24.7; HRMS (EI): calcd for C18H13N3O2 (M+) 303.1008, found 303.1007.

2.6 2-Amino-4-(3-bromophenyl)-5,6,7,8-tetrahydronaphthalene-1,3-dicarbo­nitrile (4j)

1H NMR (400 MHz, CDCl3): δ=7.61 (d, J=7.6 Hz, 1H), 7.37–7.41 (m, 2H), 7.18 (d, J=7.6 Hz, 1H), 5.05 (s, 2H), 2.98 (t, J=7.6 Hz, 2H), 2.22–2.37 (m, 2H), 1.64–1.85 (m, 2H); 13C NMR (100 MHz, CDCl3): δ=149.6, 148.3, 147.3, 139.0, 132.0, 131.5, 130.5, 127.0, 122.8, 115.4, 97.2, 96.3, 29.6, 27.3, 22.4, 21.8; HRMS (EI): calcd for C18H14BrN3 (M+) 351.0371, found 351.0360.

3 Results and discussion

3.1 The reaction of benzaldehyde, cyclopentanone and malononitrile

Previous work from our group has demonstrated that CMUI gave significant rate enhancements and improved yields in aqueous organic reactions [37–42]. Herein, we report the use of this simple and facile approach for the multicomponent synthesis of polysubstituted 3-aryl-2,6-dicyanoanilines derivatives.

In our initial study, using a mixture of benzaldehyde 1a, cyclopentanone 2a (1.0 equiv.) and malononitrile (2.2 equiv.) as a model system, we focused on the evaluation of various bases under CMUI (Table 1, entries 1–6). From the result, we found that NaOH and KOH were the most effective catalysts that selectively produced the desired products in high yields (entries 5 and 6). We subsequently examined the efficiency of the power of microwave and ultrasound irradiation (entries 6–10). The results showed that a combination of microwave irradiation at 100 W and ultrasound irradiation at 50 W gave the highest yield (entry 6). To show the usefulness of CMUI, a control experiment was carried out using the same amount of reactants (entries 11–13). The results clearly show that combined microwave and ultrasound irradiation achieved the best results in terms of both reaction time and yield. However, the conventional reaction using ethanol as the solvent went to completion with many by-products, and only 46% of desired product was obtained (entry 13). This dramatic acceleration effect of CMUI may be attributed to a combination of enforced heat transfer due to microwave irradiation and intensive mass transfer at phase interfaces caused by sonication.

Table 1

Optimization of base in the synthesis of compound 4a.a

EntryBase (equiv.)MethodTimeYield (%)b
1K2CO3 (2)CMUI (MW 100 W+US 50 W)90 s42
2NaHCO3 (3)CMUI (MW 100 W+US 50 W)90 s37
3K3PO4 (1.5)CMUI (MW 100 W+US 50 W)90 s40
4NEt3 (3)CMUI (MW 100 W+US 50 W)90 s45
5KOH (1.5)CMUI (MW 100 W+US 50 W)90 s71
6NaOH (1.5)CMUI (MW 100 W+US 50 W)90 s73
7NaOH (1.5)CMUI (MW 50 W+US 50 W)90 s47
8NaOH (1.5)CMUI (MW 200 W+US 50 W)90 s70
9NaOH (1.5)CMUI (MW 100 W+US 25 W)90 s60
10NaOH (1.5)CMUI (MW 100 W+US 100 W)90 s69
11NaOH (1.5)Ultrasound (50 W)+oil bath reflux1 h40
12NaOH (1.5)Microwave (100 W ) under reflux15 min43
13cNaOH (1.5)Conventional heating under reflux8 h46
[1]

3.2 The scope of the reactions

Having the optimized conditions in hand (Table 1, entry 6), we next investigated the scope and limitation of the process with variously substituted aldehydes 1 and cyclic ketones 2 (Table 2). A good yield of polysubstituted 3-aryl-2,6-dicyanoanilines were obtained, applying both electron-withdrawing (such as 1b, 1c, 1d) and electron-donating (such as 1e, 1f, 1g) aromatic aldehydes. Meanwhile, both cyclopentanone and cyclohexanone are well tolerated.

Table 2

Synthesis of polysubstituted 3-aryl-2,6-dicyanoanilines under CMUI.a

EntryArKetoneTime (s)Product 4Yield (%)b
1C6H5Cyclopentanone904a73
24-FC6H4Cyclopentanone904b77
33-BrC6H4Cyclopentanone904c74
42,4-diClC6H3Cyclopentanone1204d69
54-CH3C6H4Cyclopentanone1204e67
64-CH3OC6H4Cyclopentanone1104f73
73,4-(OCH2O)C6H3Cyclopentanone1004g71
8C6H5Cyclohexanone804h76
94-FC6H4Cyclohexanone804i81
103-BrC6H4Cyclohexanone804j78
112,4-diClC6H3Cyclohexanone1204k72
124-CH3C6H4Cyclohexanone1104l73
134-CH3OC6H4Cyclohexanone904m78
[2]

4 Proposed reaction pathway

According to the literature [31] and based on our experiment, the formation of 3-aryl-anthranilodinitrile derivatives could be explained by the possible reaction procedure (Scheme 1). The first step of this process involves the in situ condensation of an aldehyde and ketone with malononitrile resulting in the formation of the corresponding condensation products 5 and 6. It is noteworthy that the intermediate 5 can be determined by GC-MS. Then, compound 7 undergoes Michael addition to 5 followed by cyclization to form compound 8, which under the base condition leads to polysubstituted 3-arylanthranilodinitrile 4.

Scheme 1 Proposed reaction pathway.
Scheme 1

Proposed reaction pathway.

5 Conclusions

In conclusion, a rapid and energy-efficient protocol using simultaneous microwave and ultrasound irradiation has been developed for the synthesis of polysubstituted 3-aryl-2,6-dicyanoaniline from aromatic aldehyde, malononitrile and cyclic ketone in water. This method is simple, fast and environmentally friendly. The development of this combination technique might open an extremely promising new area in the field of aqueous organic synthesis.

Corresponding author: Gonghua Song, Shanghai Key Laboratory of Chemical Biology, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, PR China

About the authors

Huangdi Feng

Huangdi Feng received his PhD degree in applied chemistry from ECUST, with Prof. Gonghua Song. In 2010, he received a China Scholarship Council Scholarship and joined the group of Prof. Erik Van der Eycken, KU Leuven, Belgium, as a doctoral student; he received his PhD degree in chemistry in 2012. Currently, he is an assistant professor at the Chinese National Compound Library, Shanghai Institute of Materia Medica, Chinese Academy of Sciences. His research interests include the development of novel synthetic methodologies for biologically important compounds and medicinal chemistry.

Shengjie Lin

Shengjie Lin was born in Zhejiang, China, in 1987. He graduated in Chemical Engineering and Technology in 2009 and is now a PhD student in Pesticide at ECUST under the supervision of Prof. Gonghua Song. His research interests focus on the design and application of novel microwave reactors.

Jiayi Wang

Jiayi Wang was born in Hubei, China, in 1983. He graduated in Pharmaceutical Preparations in 2005 and received his PhD in Applied Chemistry in 2011 from ECUST under the supervision of Prof. Gonghua Song. Presently, he is a lecturer at the School of Pharmacy in ECUST. His research interests focus on the development of novel synthetic methodologies, pesticide design and synthesis.

Gonghua Song

Gonghua Song is Professor of Chemical Engineering at the School of Pharmacy, East China University of Science and Technology (ECUST), Shanghai, China. He was born in 1962 and obtained his PhD from ECUST in 1991. In 1999, he was appointed as a full professor. His research interests are in green chemistry and agrochemicals.

Yanqing Peng

Yanqing Peng is an Associate Professor in the Institute of Pesticides and Pharmaceuticals and Shanghai Key Laboratory of Chemical Biology at ECUST. His research program focuses on the development of new recoverable catalysts, novel routes to nanomaterials and ecofriendly agrochemicals. He has 45 internationally refereed journal papers on catalysis, green chemistry and material chemistry.

Financial support for this work from National Basic Research Program of China (973 Program) (grant 2010CB126101), National Key Technology R&D Program (grant no. 2011BAE06B05-4) are gratefully acknowledged.

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Received: 2012-7-24
Accepted: 2012-9-5
Published Online: 2012-09-28
Published in Print: 2012-10-01

©2012 Walter de Gruyter GmbH & Co. KG, Berlin/Boston

This article is distributed under the terms of the Creative Commons Attribution Non-Commercial License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

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  18. Operationally simple green synthesis of some Schiff bases using grinding chemistry technique and evaluation of antimicrobial activities
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  20. Profile of the “Christian Doppler Laboratory for Microwave Chemistry” at the Karl-Franzens-University of Graz
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  23. 2012 Michigan Green Chemistry and Engineering Conference: Driving Sustainable Manufacturing (October 26, 2012, Wayne State University, Detroit)
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https://doi.org/10.1515/gps-2012-0052
Schlagwörter für diesen Artikel
2,6-dicyanoanilines; microwave; multicomponent reaction; ultrasound; water
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Artikel in diesem Heft

  1. Masthead
  2. Masthead
  3. Graphical abstracts
  4. In this Issue
  5. Publisher’s note
  6. Green Processing and Synthesis
  7. Editorial
  8. Life is a marathon – for 80 years and not 42 km ... and for growing a h-index if you are a scientist
  9. Essay
  10. An overview of Total’s activities on alternative energies, advanced biofuels and bioproducts for energy efficiency and environmental acceptability
  11. Review
  12. Benchtop factory for cross-coupling reactions by circulatory catalyst flow using low-viscosity ionic liquid as reaction medium and catalyst support
  13. Original articles
  14. Agro-process intensification: soilborne micro-bioreactors with nitrogen fixing bacterium Azospirillum brasilense as self-sustaining biofertiliser source for enhanced nitrogen uptake by plants
  15. Multi-step processing in a microstructured flow reactor: direct nitration of propane–a proof of principle
  16. Safety, health, and environmental assessment of bioethanol production from sugarcane, corn, and corn stover
  17. Aqueous heterogeneous synthesis of polysubstituted 2,6-dicyanoanilines via combined microwave and ultrasound-assisted multicomponent reaction
  18. Operationally simple green synthesis of some Schiff bases using grinding chemistry technique and evaluation of antimicrobial activities
  19. Laboratory profile
  20. Profile of the “Christian Doppler Laboratory for Microwave Chemistry” at the Karl-Franzens-University of Graz
  21. Conference announcements
  22. Implementation of Microreactor Technology in Biotechnology (IMTB 2013)
  23. 2012 Michigan Green Chemistry and Engineering Conference: Driving Sustainable Manufacturing (October 26, 2012, Wayne State University, Detroit)
  24. 10th International Symposium on The Power of Green Energy (GAPE 2013)
  25. Cellular Materials - CELLMAT 2012 (7–9 November 2012, Dresden, Germany)
  26. Conferences 2012/2013
  27. Book review
  28. Green techniques for organic synthesis and medicinal chemistry
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