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Chemistry of Heterocyclic Compounds

, Volume 54, Issue 11, pp 1033–1039 | Cite as

Synthesis of (4-nitro-1H-indol-6-yl)- and (4-amino-1H-indol-6-yl)phosphonic acid derivatives

  • Aleksandr A. Shalimov
  • Mykola V. Kolotylo
  • Lyubov V. Babiy
  • Oksana V. Muzychka
  • Petro P. Onys’ko
  • Vladimir V. Rozhkov
Article
  • 16 Downloads

A convenient methodology for the synthesis of previously unreported (1H-indol-6-yl)phosphonic acid derivatives has been described. Reaction of (4-methyl-3,5-dinitrophenyl)phosphonates with dimethylformamide dimethyl acetal leads to the respective enamines that can be readily converted into indoles by the Batcho–Leimgruber synthetic protocol. Proper choice of reducing agent for the reductive cyclization of intermediate enamines allows to selectively obtain (4-nitro-1H-indol-6-yl)- and (4-amino-1H-indol-6-yl)phosphonates.

Keywords

4-aminoindole enamine (1H-indol-6-yl)phosphonate (4-methyl-3,5-dinitrophenyl)phosphonic acid 4-nitroindole Batcho–Leimgruber indole synthesis 

Notes

Elemental analyses were performed at Laboratory for elemental analysis of the Institute of Organic Chemistry, NAS of Ukraine.

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Copyright information

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Authors and Affiliations

  • Aleksandr A. Shalimov
    • 1
  • Mykola V. Kolotylo
    • 1
  • Lyubov V. Babiy
    • 2
  • Oksana V. Muzychka
    • 2
  • Petro P. Onys’ko
    • 1
  • Vladimir V. Rozhkov
    • 1
  1. 1.Institute of Organic Chemistry, National Academy of Sciences of UkraineKyivUkraine
  2. 2.I. F. Lab. Ltd.KyivUkraine

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