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Construction of push—pull systems using β-formyl-β-nitroenamine

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Abstract

The review is focused on the application of β-formyl-β-nitroenamines, one of the push—pull alkenes, having the biased electron density as well as an electrophilic formyl group and a nucleophilic amino group in the organic synthesis. Due to the multi-functionality, β-formyl-β-nitroenamines exhibit versatile reactivity to facilitate the synthesis of polyfunctionalized compounds possessing push—pull property. Nitroenamines serve as a synthetic equivalent of unstable nitromalonaldehyde to afford nitropyrazoles, nitropyrimidines, nitrodiazepines, and nitrophenoles upon treatment with dinucleophiles such as hydrazines, amidines, 1,2-diamines, and ketones, respectively. When active methylene compounds allowed reacting with the nitroenamines, polyfunctionalized pyridones and 2-amino-5-nitropyridines are obtained. In addition, nitroenamines undergo [4+2] self-condensation to afford 3,5-dinitropyridinium ion, which is easily trapped by benzene derivatives leading to 4-arylated 1,4-dihydropyridines.

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Authors and Affiliations

  1. School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada, Kami Kochi, 782-8502, Japan

    Y. Nakaike, H. Asahara & N. Nishiwaki

  2. Research Center of Material Science and Engineering, Kochi University of Technology, Tosayamada, Kami Kochi, 782-8502, Japan

    H. Asahara & N. Nishiwaki

Authors
  1. Y. Nakaike
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  2. H. Asahara
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  3. N. Nishiwaki
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Correspondence to N. Nishiwaki.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2129—2142, September, 2016.

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Nakaike, Y., Asahara, H. & Nishiwaki, N. Construction of push—pull systems using β-formyl-β-nitroenamine. Russ Chem Bull 65, 2129–2142 (2016). https://doi.org/10.1007/s11172-016-1561-2

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