Synthesis 2015; 47(15): 2285-2293
DOI: 10.1055/s-0034-1379917
paper
© Georg Thieme Verlag Stuttgart · New York

Efficient Synthesis of Nicotinic Acid Based Pseudopeptides Bearing an Amidoxime Function

Authors

  • Olga V. Ovdiichuk

    a   Taras Shevchenko National University of Kyiv, Chemistry Department, 64/13 Volodymyrs’ka str., Kyiv 01601, Ukraine   eMail: ov_hordiyenko@univ.kiev.ua
    b   Laboratoire de Chimie Physique Macromoléculaire, ENSIC, Université de Lorraine, 1 rue Grandville, BP 20451, 54001 Nancy, France
  • Olga V. Hordiyenko*

    a   Taras Shevchenko National University of Kyiv, Chemistry Department, 64/13 Volodymyrs’ka str., Kyiv 01601, Ukraine   eMail: ov_hordiyenko@univ.kiev.ua
  • Volodymyr V. Medviediev

    c   SSI Institute for Single Crystals, National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine
  • Oleg V. Shishkin

    c   SSI Institute for Single Crystals, National Academy of Science of Ukraine, 60 Lenina ave., Kharkiv 61001, Ukraine
    d   Department of Inorganic Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody sq., Kharkiv 61122, Ukraine
  • Axelle Arrault

    b   Laboratoire de Chimie Physique Macromoléculaire, ENSIC, Université de Lorraine, 1 rue Grandville, BP 20451, 54001 Nancy, France
Weitere Informationen

Publikationsverlauf

Received: 02. Februar 2015

Accepted after revision: 27. März 2015

Publikationsdatum:
19. Mai 2015 (online)


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Abstract

The synthesis of nicotinic acid based amino acid units bearing an amidoxime function on the pyridine ring has been developed. The starting 2-cyanonicotinic acid was efficiently coupled with methyl esters of l-α-amino acids to afford intermediate 2-cyanopyridin-3-yl-containing pseudopeptides together with the tautomeric methyl esters of (2S)-2-(7-imino-5-oxo-5,7-dihydro-6H-pyrrolo[3,4-b]pyridin-6-yl)alkanoic acids. Regioselective pyrrolidine ring opening of these esters occurred upon hydroxylamine hydrochloride treatment, giving rise to the open-chain pyridin-3-yl 2-amidoxime pseudopeptides bearing the same structure as amidoximes obtained by direct hydroxyamination of the corresponding cyano esters.

Supporting Information