E. P. Kramarova, D. N. Lyahmun, D. V. Tarasenko, A. A. Korlyukov, P. V. Dorovatovskii, T. A. Shmigol, S. Yu. Bylikin, Yu. I. Baukov, V. V. Negrebetsky, “An expedient synthesis of a picolinamide-based betain bearing a 3-sulfonatopropyl substituent”, Mendeleev Commun., 2024, Volume 34, Issue 1,Pages <nobr>126

This article is cited in 1 paper

Communications

An expedient synthesis of a picolinamide-based betain bearing a 3-sulfonatopropyl substituent

E. P. Kramarova^a, D. N. Lyahmun^a, D. V. Tarasenko^a, A. A. Korlyukov^ab, P. V. Dorovatovskii^c, T. A. Shmigol^a, S. Yu. Bylikin^d, Yu. I. Baukov^a, V. V. Negrebetsky^a

^a N.I. Pirogov Russian National Research Medical University, Moscow, Russian Federation
^b A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
^c National Research Centre 'Kurchatov Institute', Moscow, Russian Federation
^d The Open University, Walton Hall, Milton Keynes, UK

Abstract: 3-[2-(Aminocarbonyl)pyridinium-1-yl]propane-1-sulfonate, a promising medicinal betain, was prepared by a one-pot synthesis with a 89% yield via N-alkylation of ethyl picolinate with 1,3-propanesultone in MeCN followed by ammonolysis. The reaction involving picolinamide in MeOH followed by the treatment with acetone afforded a novel 3,3-dimethyl- 1-oxo-2,3-dihydro-1H-imidazo[1,5-a]pyridin-4-ium 3-methoxypropane-1-sulfonate.

Keywords: picolinic acid derivatives, sulfobetains, sultones, alkylation, pyridinium salts, imidazo[1,5-a]pyridin-4-ium salts, NMR and FT–IR spectroscopy, X-ray study.

Language: English

DOI: 10.1016/j.mencom.2024.01.038

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