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Features of the synthesis of isatins and isoindigo derivatives bearing long-chain haloalkyl substituents

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Abstract

The features of the synthesis of long-chain isatin and isoindigo derivatives were demonstrated by the example of bromododecyl representatives. It was shown that the synthesis of bromododecylisatin was accompanied by the formation of the bis-isatin even at low temperatures. The deoxygenation of 1-(12-bromododecyl)isatin by tris(diethylamino)phosphine led to the formation of novel bis(bromoalkyl)isoindigo which easily reacted with nucleophilic reagents resulting in amino- or chloro-derivatives and phosphonium salts. The reaction of 1,1′-bis(bromododecyl)isoindigo with isatin sodium salt in slightly alkaline medium afforded mainly IZIN-12 and bis(2,3-dioxindolin-1-yl)isoindigo. In addition, several unexpected products were separated from this reaction.

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Acknowledgments

This work is supported by the Russian Foundation for Basic Research (Grant No. 12-03-00,164-a) and by Program No. 6 of the Division of Chemistry and Material Sciences of the Russian Academy of Sciences.

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Authors and Affiliations

  1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

    Irina P. Romanova, Gulshat G. Yusupova, Shamil K. Latypov, Anna G. Strelnik, Ildar Kh. Rizvanov, Andrei V. Bogdanov, Vladimir F. Mironov & Oleg G. Sinyashin

Authors
  1. Irina P. Romanova
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  2. Gulshat G. Yusupova
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  3. Shamil K. Latypov
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  4. Anna G. Strelnik
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  5. Ildar Kh. Rizvanov
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  6. Andrei V. Bogdanov
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  7. Vladimir F. Mironov
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  8. Oleg G. Sinyashin
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Corresponding author

Correspondence to Andrei V. Bogdanov.

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Romanova, I.P., Yusupova, G.G., Latypov, S.K. et al. Features of the synthesis of isatins and isoindigo derivatives bearing long-chain haloalkyl substituents. Monatsh Chem 146, 365–374 (2015). https://doi.org/10.1007/s00706-014-1356-9

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  • DOI: https://doi.org/10.1007/s00706-014-1356-9

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