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Synthesis of polyfunctionalized pyrido[1,2-a]pyrazines and pyrazino[1,2-a]quinolines via one-pot multicomponent reactions

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Abstract

An efficient, straightforward, and general method for the synthesis of pyrido[1,2-a]pyrazine and pyrazino[1,2-a]quinoline derivatives via a one-pot three-component reaction between cyclic enamineones, aromatic aldehydes, and 1,3-dicarbonyl compound is reported. On our knowledge, this is the first reported one-pot multicomponent reaction for synthesis of pyrido[1,2-a]pyrazine and pyrazino[1,2-a]quinoline derivatives. A proposed reaction pathway for the synthesis has been proved experimentally, consisting in addition of 3-(alkoxycarbonylmethylidene)piperazine-2-ones to the products of condensation of aromatic aldehydes and 1,3-dicarbonyl compounds, followed by further cyclocondensation Michael addition. The structure of the thirteen new compounds was proven by elemental and spectral analysis (1H and 13C NMR, HPLC/MS, and FT-IR).

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Authors and Affiliations

  1. Yuriy Fedkovych Chernivtsi National University, 2 Kotsyubinsky St., Chernivtsi, 58012, Ukraine

    Renata I. Eften’eva, Oleg V. Kushnir & Oleksandr S. Lyavinets

  2. Faculty of Chemistry, “Al. I. Cuza” University of Iasi, Bd. Carol 11, 700506, Iasi, Romania

    Ionel I. Mangalagiu

  3. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kiev, 02094, Ukraine

    Myhailo V. Vovk

Authors
  1. Renata I. Eften’eva
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  2. Oleg V. Kushnir
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  3. Oleksandr S. Lyavinets
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  4. Ionel I. Mangalagiu
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  5. Myhailo V. Vovk
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Corresponding author

Correspondence to Oleg V. Kushnir.

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Eften’eva, R.I., Kushnir, O.V., Lyavinets, O.S. et al. Synthesis of polyfunctionalized pyrido[1,2-a]pyrazines and pyrazino[1,2-a]quinolines via one-pot multicomponent reactions. Monatsh Chem 147, 2127–2133 (2016). https://doi.org/10.1007/s00706-016-1836-1

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  • DOI: https://doi.org/10.1007/s00706-016-1836-1

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