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Reaction of pyrrolo[2,1-a]isoquinoline-2,3-diones with carbon-centered nucleophiles

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Abstract

Knoevenagel condensations of 5,5-dimethyl-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-diones with malononitrile, ethyl cyanoacetate, indan-1,3-dione, and Drotaverine base involved the ketone carbonyl group in the former with formation of deeply colored dark blue substances. The lactam ring in the products can be opened by the action of nitrogen-centered nucleophiles, e.g., p-toluidine. The reaction of 5,5-dimethyl-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-dione with methyl magnesium iodide gave 2-hydroxy-2,5,5-trimethyl-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinolin-3-one.

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, ul. Lenina 48, Perm, 614990, Russia

    O. V. Surikova, A. G. Mikhailovskii, N. N. Polygalova & M. I. Vakhrin

Authors
  1. O. V. Surikova
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  2. A. G. Mikhailovskii
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  3. N. N. Polygalova
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  4. M. I. Vakhrin
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Correspondence to O. V. Surikova.

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Original Russian Text © O.V. Surikova, A.G. Mikhailovskii, N.N. Polygalova, M.I. Vakhrin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 6, pp. 856–858.

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Surikova, O.V., Mikhailovskii, A.G., Polygalova, N.N. et al. Reaction of pyrrolo[2,1-a]isoquinoline-2,3-diones with carbon-centered nucleophiles. Russ J Org Chem 44, 845–848 (2008). https://doi.org/10.1134/S1070428008060110

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  • DOI: https://doi.org/10.1134/S1070428008060110

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