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4-(Propargylthio)sydnone imines: synthesis and reactivity in the azide--alkyne cycloaddition

Natalia V. Kalganova 1
Natalia V. Kalganova
, 
Danil N. Bryksin 2
Danil N. Bryksin
, 
Alexander Fedorovich Smol'yakov 1
Alexander Fedorovich Smol'yakov
, 
Ilya Aleksandrovich Cherepanov 1
Ilya Aleksandrovich Cherepanov
10.71267/mencom.7908
Published 2026-02-03
Communication , Volume 36, Issue 2, 180-182
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Kalganova N. V. et al. 4-(Propargylthio)sydnone imines: synthesis and reactivity in the azide--alkyne cycloaddition // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 180-182.
GOST all authors (up to 50) Copy
Kalganova N. V., Bryksin D. N., Smol'yakov A. F., Cherepanov I. A. 4-(Propargylthio)sydnone imines: synthesis and reactivity in the azide--alkyne cycloaddition // Mendeleev Communications. 2026. Vol. 36. No. 2. pp. 180-182.
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TY - JOUR
DO - 10.71267/mencom.7908
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7908
TI - 4-(Propargylthio)sydnone imines: synthesis and reactivity in the azide--alkyne cycloaddition
T2 - Mendeleev Communications
AU - Kalganova, Natalia V.
AU - Bryksin, Danil N.
AU - Smol'yakov, Alexander Fedorovich
AU - Cherepanov, Ilya Aleksandrovich
PY - 2026
DA - 2026/02/03
PB - Mendeleev Communications
SP - 180-182
IS - 2
VL - 36
ER -
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@article{2026_Kalganova,
author = {Natalia V. Kalganova and Danil N. Bryksin and Alexander Fedorovich Smol'yakov and Ilya Aleksandrovich Cherepanov},
title = {4-(Propargylthio)sydnone imines: synthesis and reactivity in the azide--alkyne cycloaddition},
journal = {Mendeleev Communications},
year = {2026},
volume = {36},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7908},
number = {2},
pages = {180--182},
doi = {10.71267/mencom.7908}
}
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Kalganova, Natalia V., et al. “4-(Propargylthio)sydnone imines: synthesis and reactivity in the azide--alkyne cycloaddition.” Mendeleev Communications, vol. 36, no. 2, Feb. 2026, pp. 180-182. https://mendcomm.colab.ws/publications/10.71267/mencom.7908.

Keywords

azide--alkyne cycloaddition
lithiation
mesoionic compounds
NO donors
sulfides
sydnone imines
terminal acetylenes

Abstract

A convenient and general method has been developed for the synthesis of previously scarcely accessible sydnone imines bearing a terminal alkyne moiety via the lithiation at the position 4 followed by treatment with propargyl bromide. The thus obtained 4-propargylthio derivatives were subjected to azide–alkyne cycloaddition to produce the corresponding 1,2,3-triazole–sydnone imine conjugates. For the first time, a lipoic acid conjugate incorporating the NO-donor fragment of Molsidomine has been synthesized.

Funders

Ministry of Education and Science of the Russian Federation
58.3

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