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Unusual cyclization of N-imidazolyl quinone imines with the formation of thiadiazole ring and its subsequent recyclization

Alexandra Alexandrovna Kolodina 1
Alexandra Alexandrovna Kolodina
, 
Dmitry Vladimirovich Steglenko 1
Dmitry Vladimirovich Steglenko
, 
Evgeniya Sergeevna Khodykina 1
Evgeniya Sergeevna Khodykina
, 
Natalia Igorevna Gaponenko 2
Natalia Igorevna Gaponenko
, 
Maria Sergeevna Galkina 1
Maria Sergeevna Galkina
,  , 
Anatolii Viktorovich Metelitsa 1
Anatolii Viktorovich Metelitsa
2 Information Center for Expertise, Accounting and Analysis of Circulation of Medical Products, Rostov-on-Don, Russian Federation
10.1016/j.mencom.2022.05.032
Published 2022-04-29
Communication , Volume 32, Issue 3, 386-389
3
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Kolodina A. A. et al. Unusual cyclization of N-imidazolyl quinone imines with the formation of thiadiazole ring and its subsequent recyclization // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 386-389.
GOST all authors (up to 50) Copy
Kolodina A. A., Steglenko D. V., Khodykina E. S., Gaponenko N. I., Galkina M. S., Demidov O. P., Metelitsa A. V. Unusual cyclization of N-imidazolyl quinone imines with the formation of thiadiazole ring and its subsequent recyclization // Mendeleev Communications. 2022. Vol. 32. No. 3. pp. 386-389.
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TY - JOUR
DO - 10.1016/j.mencom.2022.05.032
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.032
TI - Unusual cyclization of N-imidazolyl quinone imines with the formation of thiadiazole ring and its subsequent recyclization
T2 - Mendeleev Communications
AU - Kolodina, Alexandra Alexandrovna
AU - Steglenko, Dmitry Vladimirovich
AU - Khodykina, Evgeniya Sergeevna
AU - Gaponenko, Natalia Igorevna
AU - Galkina, Maria Sergeevna
AU - Demidov, Oleg Petrovich
AU - Metelitsa, Anatolii Viktorovich
PY - 2022
DA - 2022/04/29
PB - Mendeleev Communications
SP - 386-389
IS - 3
VL - 32
ER -
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@article{2022_Kolodina,
author = {Alexandra Alexandrovna Kolodina and Dmitry Vladimirovich Steglenko and Evgeniya Sergeevna Khodykina and Natalia Igorevna Gaponenko and Maria Sergeevna Galkina and Oleg Petrovich Demidov and Anatolii Viktorovich Metelitsa},
title = {Unusual cyclization of N-imidazolyl quinone imines with the formation of thiadiazole ring and its subsequent recyclization},
journal = {Mendeleev Communications},
year = {2022},
volume = {32},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.032},
number = {3},
pages = {386--389},
doi = {10.1016/j.mencom.2022.05.032}
}
MLA
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Kolodina, Alexandra Alexandrovna, et al. “Unusual cyclization of N-imidazolyl quinone imines with the formation of thiadiazole ring and its subsequent recyclization.” Mendeleev Communications, vol. 32, no. 3, Apr. 2022, pp. 386-389. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2022.05.032.

Keywords

N-hetaryl quinone imines
DFT calculations
imidazo[2,1-b][1,3,4]thiadiazoles
imidazo[2,1-b]thiazoles
recyclization

Abstract

2,6-Di-tert-butyl-4-{[2-(2-aryl-2-oxoethylthio)-1H-imidazol-1-yl]imino}cyclohexa-2,5-dien-1-ones under the action of bases give products of the 2,3-dihydroimidazo[2,1-b]thiazol- 3-ol series by subsequent recyclization reaction of the intermediate imidazo[2,1-b][1,3,4]thiadiazoles. The structure of imidazo[2,1-b]thiazol-3-ol is supported by the X-ray diffraction. The features of the cyclization processes of quinone imine derivatives were stimulated by DFT calculations using the wB97XD/6-311++G** method.

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