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

Eugeniya Petrovna Kramarova 1
Eugeniya Petrovna Kramarova
, 
Dmitry Nikolaevich Lyahmun 1
Dmitry Nikolaevich Lyahmun
, 
Dmitry Victorovich Tarasenko 1
Dmitry Victorovich Tarasenko
, 
Alexander Aleksandrovich Korlyukov 1, 2
Alexander Aleksandrovich Korlyukov
, 
Pavel Vladimirovich Dorovatovskii 3
Pavel Vladimirovich Dorovatovskii
, 
Tatiana Anatol'evna Shmigol 1
Tatiana Anatol'evna Shmigol
, 
Sergey Yur'evich Bylikin 4
Sergey Yur'evich Bylikin
, 
Yuri Ivanovich Baukov 1
Yuri Ivanovich Baukov
, 
Vadim Vital'evich Negrebetsky 1
Vadim Vital'evich Negrebetsky
1 N.I. Pirogov Russian National Research Medical University, Moscow, Russian Federation
2 A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Moscow, Russian Federation
3 National Research Centre 'Kurchatov Institute', Moscow, Russian Federation
4 The Open University, Walton Hall, Milton Keynes, UK
10.1016/j.mencom.2024.01.038
Published 2023-12-25
Communication , Volume 34, Issue 1, 126-128
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Kramarova E. P. et al. An expedient synthesis of a picolinamide-based betain bearing a 3-sulfonatopropyl substituent // Mendeleev Communications. 2023. Vol. 34. No. 1. pp. 126-128.
GOST all authors (up to 50) Copy
Kramarova E. P., Lyahmun D. N., Tarasenko D. V., Korlyukov A. A., Dorovatovskii P. V., Shmigol T. A., Bylikin S. Y., Baukov Y. I., Negrebetsky V. V. An expedient synthesis of a picolinamide-based betain bearing a 3-sulfonatopropyl substituent // Mendeleev Communications. 2023. Vol. 34. No. 1. pp. 126-128.
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TY - JOUR
DO - 10.1016/j.mencom.2024.01.038
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.038
TI - An expedient synthesis of a picolinamide-based betain bearing a 3-sulfonatopropyl substituent
T2 - Mendeleev Communications
AU - Kramarova, Eugeniya Petrovna
AU - Lyahmun, Dmitry Nikolaevich
AU - Tarasenko, Dmitry Victorovich
AU - Korlyukov, Alexander Aleksandrovich
AU - Dorovatovskii, Pavel Vladimirovich
AU - Shmigol, Tatiana Anatol'evna
AU - Bylikin, Sergey Yur'evich
AU - Baukov, Yuri Ivanovich
AU - Negrebetsky, Vadim Vital'evich
PY - 2023
DA - 2023/12/25
PB - Mendeleev Communications
SP - 126-128
IS - 1
VL - 34
ER -
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@article{2023_Kramarova,
author = {Eugeniya Petrovna Kramarova and Dmitry Nikolaevich Lyahmun and Dmitry Victorovich Tarasenko and Alexander Aleksandrovich Korlyukov and Pavel Vladimirovich Dorovatovskii and Tatiana Anatol'evna Shmigol and Sergey Yur'evich Bylikin and Yuri Ivanovich Baukov and Vadim Vital'evich Negrebetsky},
title = {An expedient synthesis of a picolinamide-based betain bearing a 3-sulfonatopropyl substituent},
journal = {Mendeleev Communications},
year = {2023},
volume = {34},
publisher = {Mendeleev Communications},
month = {Dec},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.038},
number = {1},
pages = {126--128},
doi = {10.1016/j.mencom.2024.01.038}
}
MLA
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Kramarova, Eugeniya Petrovna, et al. “An expedient synthesis of a picolinamide-based betain bearing a 3-sulfonatopropyl substituent.” Mendeleev Communications, vol. 34, no. 1, Dec. 2023, pp. 126-128. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.01.038.
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Keywords

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

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.

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