Efficient method for the synthesis of polysubstituted 2,6-dicyanoanilines by one-pot three-component tandem reaction of malononitrile with α,β-unsaturated imines
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Wei Chen
Abstract
A facile and efficient one-pot synthesis of polysubstituted benzenes was achieved via the Michael addition of malononitrile with α,β-unsaturated imines and a sequential tandem reaction. This reaction generates polysubstituted 2,6-dicyanoanilines in high yields (15 examples, isolated yields of 57-91 %), and proceeds under mild reaction conditions (60°C, 10 min). In addition, a possible mechanism accounting for the reaction is proposed.
References
Boger, D. L., Corbett, W. L., Curran, T. T., & Kasper, A. M. (1991). Inverse electron-demand Diels-Alder reactions of N-sulfonyl .alpha.,.beta.-unsaturated imines: a general approach to implementation of the 4.pi. participation of 1-aza-1,3-butadienes in Diels-Alder reactions. Journal of the American Chemical Society, 113, 1713-1729. DOI: 10.1021/ja00005a040.10.1021/ja00005a040Suche in Google Scholar
Chen, W., Yu, W. G., Shi, H. B., & Lu, X. Y. (2012). Selective synthesis of E-isomers of aldoximes via a domino aza- Michael/retro-Michael reaction. Chemical Papers, 66, 308-311. DOI: 10.2478/s11696-012-0137-3.10.2478/s11696-012-0137-3Suche in Google Scholar
Cui, S. L., Lin, X. F., &Wang, Y. G. (2005). Parallel synthesis of strongly fluorescent polysubstituted 2,6-dicyanoanilines via microwave-promoted multicomponent reaction. Journal of Organic Chemistry, 70, 2866-2869. DOI: 10.1021/jo047823h.10.1021/jo047823hSuche in Google Scholar PubMed
Das, P., Butcher, R. J., & Mukhopadhyay, C. (2012). Zinc titanate nanopowder: an advanced nanotechnology based recyclable heterogeneouscatalyst for the one-pot selective synthesis of self-aggregated low-molecular mass acceptor-donor- acceptor-acceptor systems and acceptor-donor-acceptor triads. Green Chemistry, 14, 1376-1387. DOI: 10.1039/c2gc16 641k.Suche in Google Scholar
Enders, D., Grondal, C., & H¨uttl, M. R. M. (2007). Asymmetric organocatalytic domino reactions. Angewandte Chemie International Edition, 46, 1570-1581. DOI: 10.1002/anie.200603129.10.1002/anie.200603129Suche in Google Scholar PubMed
Esquivias, J., Arrayás, R. G., & Carretero, J. C. (2007). Catalytic asymmetric inverse-electron-demand Diels-Alder reaction of N-sulfonyl-1-aza-1,3-dienes. Journal of the American Chemical Society, 129, 1480-1481. DOI: 10.1021/ja0658766.10.1021/ja0658766Suche in Google Scholar PubMed
Goel, A., & Singh, F. V. (2005). Regioselective synthesis of functionally congested biaryls through a novel C-C bond formation reaction. Tetrahedron Letters, 46, 5585-5587. DOI: 10.1016/j.tetlet.2005.06.034.10.1016/j.tetlet.2005.06.034Suche in Google Scholar
Li, J. L., Liu, T. Y., & Chen, Y. C. (2012). Aminocatalytic asymmetric Diels-Alder reactions via HOMO activation. Accounts of Chemical Research, 45, 1491-1500. DOI: 10.1021/ar3000822.10.1021/ar3000822Suche in Google Scholar PubMed
Lu, P., & Wang, Y. G. (2010). Strategies for heterocyclic synthesis via cascade reactions based on ketenimines. Synlett, 2010, 165-173. DOI: 10.1055/s-0029-1218558. Raghukumar, V., Murugan, P., & Ramakrishnan, V. T. (2001). A facile one pot synthesis of m-terphenyl and biaryl derivatives. Synthetic Communications, 31, 3497-3505. DOI: 10.1081/scc-100106211.10.1081/SCC-100106211Suche in Google Scholar
Rong, L., Han, H., Yang, F., Yao, H., Jiang, H., & Tu, S. J. (2007). Efficient one-pot synthesis of 2-amino-4,6- diarylbenzene-1,3-dicarbonitrile under solvent-free conditions. Synthetic Communications, 37, 3767-3772. DOI: 10.1080/00397910701569684.10.1080/00397910701569684Suche in Google Scholar
Saito, S., & Yamamoto, Y. (2000). Recent advances in the transition-metal-catalyzed regioselective approaches to polysubstituted benzene derivatives. Chemical Reviews, 100, 2901-2916. DOI: 10.1021/cr990281x.10.1021/cr990281xSuche in Google Scholar PubMed
Sepioł, J., & Milart, P. (1985). Elimination of the nitrile group from o-aminonitriles-IV: A new and efficient synthesis of 3,5-diarylaminobenzenes from arylidenemalonodinitriles and 1-arylethylidenemalonodinitriles. Tetrahedron, 41, 5261-5265. DOI: 10.1016/s0040-4020(01)96775-4.10.1016/S0040-4020(01)96775-4Suche in Google Scholar
Wang, J. F., Li, Q., Qi, C., Liu, Y., Ge, Z. M., & Li, R. T. (2010). Primary 1,2-diamine catalysis III: an unexpected domino reaction for the synthesis of multisubstituted cyclohexa-1,3- dienamines. Organic & Biomolecular Chemistry, 8, 4240-4242. DOI: 10.1039/c0ob00089b.10.1039/c0ob00089bSuche in Google Scholar PubMed
Xin, X., Wang, Y., Xu,W., Lin, Y. J, Duan, H. F., & Dong, D. W. (2010). A facile and efficient one-pot synthesis of polysubstituted benzenes in guanidinium ionic liquids. Green Chemistry, 12, 893-898. DOI: 10.1039/b921390b.10.1039/b921390bSuche in Google Scholar
Yan, C. G.,Wang, Q. F., Song, X. K., & Sun, J. (2009). One-step synthesis of pyrido[1,2-a]benzimidazole derivatives by a novel multicomponent reaction of chloroacetonitrile, malononitrile, aromatic aldehyde, and pyridine. Journal of Organic Chemistry, 74, 710-718. DOI: 10.1021/jo802166t. 10.1021/jo802166tSuche in Google Scholar PubMed
© 2015 Institute of Chemistry, Slovak Academy of Sciences
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Artikel in diesem Heft
- Voltammetric determination of B1 and B6 vitamins using a pencil graphite electrode
- An electrochemical sensor for sensitive determination of nitrites based on Ag–Fe3O4–graphene oxide magnetic nanocomposites
- Effect of influent nitrogen concentration on feasibility of short-cut nitrification during wastewater treatment in activated sludge systems
- Assessment of Urtica as a low-cost adsorbent for methylene blue removal: kinetic, equilibrium, and thermodynamic studies
- Electrode and electrodeless impedance measurement for determination of orange juices parameters
- Evaluation of oxidative stability of vegetable oils enriched with herb extracts by EPR spectroscopy
- Electrosynthesis of poly(p-phenylene) and poly(p-phenylene/pyrrole) films under controlled humidity
- Synthesis, characterisation, and electrical properties of novel nanostructured conducting poly(aniline-co-m-chloroaniline) with incorporated silver particles
- Heterocyclisation of substituted ylidenethiocarbonohydrazides using dimethyl acetylenedicarboxylate
- Newly synthesized indolizine derivatives – antimicrobial and antimutagenic properties
- Synthesis and insecticidal activity of anthranilic diamides with hydrazone substructure
- Effect of alkylated diphenylamine on thermal-oxidative degradation behavior of poly-α-olefin
- Novel pathways of interaction of maleic anhydride derivatives with phosphorus(III) compounds: synthesis and characterisation of N,N,N′,N′ -tetraethyl-2,3-diphenylbut-2-enediamide and 3-dihydrofuranylidene-4-phosphorylidene–oxolane-2,5,5′-trione
- Efficient method for the synthesis of polysubstituted 2,6-dicyanoanilines by one-pot three-component tandem reaction of malononitrile with α,β-unsaturated imines
