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An unexpected product of the reaction between N-hydroxy-6-methyluracil-5-carboximidoyl chloride and thioureas

Inna Borisovna Chernikova 1
Inna Borisovna Chernikova
, 
Alexander Nikolaevich Lobov 1
Alexander Nikolaevich Lobov
, 
Ekaterina Sergeevna Meshcheryakova 2
Ekaterina Sergeevna Meshcheryakova
, 
Leonard Mukhibovich Khalilov 2
Leonard Mukhibovich Khalilov
, 
Marat Sabirovich Yunusov 1
Marat Sabirovich Yunusov
1 Ufa Institute of Chemistry, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
2 Institute of Petrochemistry and Catalysis, Ufa Federal Research Centre of the Russian Academy of Sciences, Ufa, Russian Federation
10.1016/j.mencom.2023.09.039
Published 2023-09-01
Communication , Volume 33, Issue 5, 714-716
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Chernikova I. B. et al. An unexpected product of the reaction between N-hydroxy-6-methyluracil-5-carboximidoyl chloride and thioureas // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 714-716.
GOST all authors (up to 50) Copy
Chernikova I. B., Lobov A. N., Meshcheryakova E. S., Khalilov L. M., Yunusov M. S. An unexpected product of the reaction between N-hydroxy-6-methyluracil-5-carboximidoyl chloride and thioureas // Mendeleev Communications. 2023. Vol. 33. No. 5. pp. 714-716.
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TY - JOUR
DO - 10.1016/j.mencom.2023.09.039
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.039
TI - An unexpected product of the reaction between N-hydroxy-6-methyluracil-5-carboximidoyl chloride and thioureas
T2 - Mendeleev Communications
AU - Chernikova, Inna Borisovna
AU - Lobov, Alexander Nikolaevich
AU - Meshcheryakova, Ekaterina Sergeevna
AU - Khalilov, Leonard Mukhibovich
AU - Yunusov, Marat Sabirovich
PY - 2023
DA - 2023/09/01
PB - Mendeleev Communications
SP - 714-716
IS - 5
VL - 33
ER -
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@article{2023_Chernikova,
author = {Inna Borisovna Chernikova and Alexander Nikolaevich Lobov and Ekaterina Sergeevna Meshcheryakova and Leonard Mukhibovich Khalilov and Marat Sabirovich Yunusov},
title = {An unexpected product of the reaction between N-hydroxy-6-methyluracil-5-carboximidoyl chloride and thioureas},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.039},
number = {5},
pages = {714--716},
doi = {10.1016/j.mencom.2023.09.039}
}
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Chernikova, Inna Borisovna, et al. “An unexpected product of the reaction between N-hydroxy-6-methyluracil-5-carboximidoyl chloride and thioureas.” Mendeleev Communications, vol. 33, no. 5, Sep. 2023, pp. 714-716. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.09.039.

Keywords

6-methyluracil
isothiocyanates.
N-hydroxy-6-methyluracil-5-carboximidoyl chloride
nitrile N-oxides
thioureas

Abstract

5-Isothiocyanato-6-methylpyrimidine-2,4(1H,3H)-dione was formed in the course of the reaction between N-hydroxy-6-methyluracil-5-carboximidoyl chloride and a series of thioureas in MeOH in the presence of Et3N. The transformation follows the Hoffman rearrangement mechanism, with the nitrile N-oxide being the key intermediate.

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