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Efficient Synthesis of Nicotinic Acid Based Pseudopeptides Bearing an Amidoxime Function

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―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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https://hal.univ-lorraine.fr/hal-01497725
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Submitted on : Wednesday, March 29, 2017 - 10:46:46 AM
Last modification on : Tuesday, September 27, 2022 - 4:11:15 AM

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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, Georg Thieme Verlag, 2015, 47 (15), pp.2285-2293. ⟨10.1055/s-0034-1379917⟩. ⟨hal-01497725⟩

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