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Article Dans Une Revue Synthesis: Journal of Synthetic Organic Chemistry Année : 2015

Efficient Synthesis of Nicotinic Acid Based Pseudopeptides Bearing an Amidoxime Function

Résumé

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―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)alkano ic 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.
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Dates et versions

hal-01497725 , version 1 (29-03-2017)

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Olga V. Ovdiichuk, Olga V. Hordiyenko, Volodymyr V. Medviediev, Oleg V. Shishkin, Axelle Arrault. Efficient Synthesis of Nicotinic Acid Based Pseudopeptides Bearing an Amidoxime Function. Synthesis: Journal of Synthetic Organic Chemistry, 2015, 47 (15), pp.2285-2293. ⟨10.1055/s-0034-1379917⟩. ⟨hal-01497725⟩
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