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New multicomponent method for the synthesis of polyhydrogenated pyrazino[1,2-a]quinolines

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Chemistry of Heterocyclic Compounds Aims and scope

A new one-pot method for the synthesis of 2,3,4,6,7,8,9,10-octahydro-1H-pyrazino[1,2-a]quinolines was developed based on a three-component reaction between methyl (3-oxopiperazin-2-ylidene)acetate, aromatic aldehydes, and cyclohexane-1,3-diones. It was shown by HPLC-MS analysis that this cascade reaction involved a sequence of steps including condensation between 1,3-diketone and aldehyde, addition of heterocyclic enaminone as a C-nucleophile, and intramolecular heterocyclization.

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The work was performed with financial support from the Russian Ministry of Education and Science within the framework of the State Assignment for scientific activity to Higher Education Istitutions for years 2014–2016 (Project No. 4.2100.2014/K).

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Authors and Affiliations

  1. Voronezh State University, 1 Universitetskaya Sq., Voronezh, 394018, Russia

    Svetlana M. Medvedeva, Khidmet S. Shikhlaliev & Mikhail Yu. Krysin

  2. N. N. Burdenko Voronezh State Medical University, 10 Studencheskaya St., Voronezh, 394036, Russia

    Irina V. Gotsak

Authors
  1. Svetlana M. Medvedeva
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  2. Khidmet S. Shikhlaliev
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  3. Mikhail Yu. Krysin
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  4. Irina V. Gotsak
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Correspondence to Khidmet S. Shikhlaliev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(5), 309–315

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Medvedeva, S.M., Shikhlaliev, K.S., Krysin, M.Y. et al. New multicomponent method for the synthesis of polyhydrogenated pyrazino[1,2-a]quinolines. Chem Heterocycl Comp 52, 309–315 (2016). https://doi.org/10.1007/s10593-016-1876-9

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