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Base-catalyzed heterocyclization of 2-(R-ethynyl)benzohydroxamic acids

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Abstract

Sonogashira alkynylation of methyl 2-iodobenzoate with terminal acetylenes gave a series of methyl 2-(alk-1-yn-1-yl)benzoates which reacted with hydroxylamine in boiling methanol to produce five- or six-membered N-hydroxy lactams, 3-R-methylidene-2-hydroxy-2,3-dihydroisoindol-1-ones or 3-R-isoquinolin-1(2H)-ones, depending on the acetylenic substituent nature.

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Authors and Affiliations

  1. Voevodskii Institute of Chemical Kinetics and Combustion, Siberian Branch, Russian Academy of Sciences, ul. Institutskaya 3, Novosibirsk, 630090, Russia

    S. F. Vasilevskii, T. F. Mikhailovskaya & A. A. Stepanov

  2. Novosibirsk State University, ul. Pirogova 2, Novosibirsk, 630090, Russia

    S. F. Vasilevskii, A. A. Stepanov & V. I. Mamatyuk

  3. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, pr. Akademika Lavrent’eva 9, Novosibirsk, 630090, Russia

    V. I. Mamatyuk & D. S. Fadeev

Authors
  1. S. F. Vasilevskii
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  2. T. F. Mikhailovskaya
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  3. A. A. Stepanov
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  4. V. I. Mamatyuk
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  5. D. S. Fadeev
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Corresponding author

Correspondence to S. F. Vasilevskii.

Additional information

Original Russian Text © S.F. Vasilevskii, T.F. Mikhailovskaya, A.A. Stepanov, V.I. Mamatyuk, D.S. Fadeev, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 4, pp. 518–521.

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Vasilevskii, S.F., Mikhailovskaya, T.F., Stepanov, A.A. et al. Base-catalyzed heterocyclization of 2-(R-ethynyl)benzohydroxamic acids. Russ J Org Chem 50, 506–509 (2014). https://doi.org/10.1134/S1070428014040101

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  • DOI: https://doi.org/10.1134/S1070428014040101

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