SYNTHESIS OF (4-NITRO-1<i>H</i>-INDOL-6-YL)- AND (4-AMINO-1<i>H</i>-INDOL-6-YL)PHOSPHONIC ACID DERIVATIVES

Authors

  • Alexander A. Shalimov Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine
  • Mykola V. Kolotylo Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine
  • Lyubov V. Babiy I. F. Lab. Ltd., 5 Murmanska St., Kyiv 02660, Ukraine
  • Oksana V. Muzychka I. F. Lab. Ltd., 5 Murmanska St., Kyiv 02660, Ukraine
  • Petro P. Onys'ko Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine
  • Vladimir V. Rozhkov Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02660, Ukraine

DOI:

https://doi.org/10.1007/4749

Keywords:

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

Abstract

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.

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Published

2018-12-12

Issue

Vol. 54 No. 11 (2018)

Section

Original Papers