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Three-component cyclization of hydroxylamino-substituted quinoline with reactive methylene compounds and formaldehyde: new method for the synthesis of 7-(isoxazolidin-2-yl)-6-fluoroquinolones

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Abstract

A one-step procedure was developed for the synthesis of new 6-fluoro-7-(isoxazolidin-2-yl)-4-oxo-1,4-dihydroquinolines. The procedure is based on the 1,3-dipolar cycloaddition of the azomethine oxide and 1,1-disubstituted alkenes, which are generated in situ from 6-fluoro-7-hydroxylamino-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and CH-active compounds (dialkyl malonates, ethyl acetoacetate), respectively, in the presence of formaldehyde at 100—120 °C.

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Authors and Affiliations

  1. Ural State Technical University, 19 ul. Mira, 620002, Ekaterinburg, Russian Federation

    N. N. Mochulskaya, L. P. Sidorova & V. N. Charushin

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  1. N. N. Mochulskaya
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  2. L. P. Sidorova
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  3. V. N. Charushin
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Mochulskaya, N.N., Sidorova, L.P. & Charushin, V.N. Three-component cyclization of hydroxylamino-substituted quinoline with reactive methylene compounds and formaldehyde: new method for the synthesis of 7-(isoxazolidin-2-yl)-6-fluoroquinolones. Russian Chemical Bulletin 51, 2106–2108 (2002). https://doi.org/10.1023/A:1021680414417

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  • DOI: https://doi.org/10.1023/A:1021680414417

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