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Unexpected transamination between 2-aminoazoles and N-iodoacetyl azoles

Nina Olegovna Yarosh 1
Nina Olegovna Yarosh
, 
Ivan Aphanas'evich Dorofeev 1
Ivan Aphanas'evich Dorofeev
, 
Larisa Vladimirovna Zhilitskaya 1
Larisa Vladimirovna Zhilitskaya
, 
Bagrat Armenovich Shainyan 1
Bagrat Armenovich Shainyan
10.1016/j.mencom.2024.02.039
Published 2024-02-19
Communication , Volume 34, Issue 2, 279-281
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Yarosh N. O. et al. Unexpected transamination between 2-aminoazoles and N-iodoacetyl azoles // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 279-281.
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Yarosh N. O., Dorofeev I. A., Zhilitskaya L. V., Shainyan B. A. Unexpected transamination between 2-aminoazoles and N-iodoacetyl azoles // Mendeleev Communications. 2024. Vol. 34. No. 2. pp. 279-281.
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TY - JOUR
DO - 10.1016/j.mencom.2024.02.039
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.039
TI - Unexpected transamination between 2-aminoazoles and N-iodoacetyl azoles
T2 - Mendeleev Communications
AU - Yarosh, Nina Olegovna
AU - Dorofeev, Ivan Aphanas'evich
AU - Zhilitskaya, Larisa Vladimirovna
AU - Shainyan, Bagrat Armenovich
PY - 2024
DA - 2024/02/19
PB - Mendeleev Communications
SP - 279-281
IS - 2
VL - 34
ER -
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@article{2024_Yarosh,
author = {Nina Olegovna Yarosh and Ivan Aphanas'evich Dorofeev and Larisa Vladimirovna Zhilitskaya and Bagrat Armenovich Shainyan},
title = {Unexpected transamination between 2-aminoazoles and N-iodoacetyl azoles},
journal = {Mendeleev Communications},
year = {2024},
volume = {34},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.039},
number = {2},
pages = {279--281},
doi = {10.1016/j.mencom.2024.02.039}
}
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Yarosh, Nina Olegovna, et al. “Unexpected transamination between 2-aminoazoles and N-iodoacetyl azoles.” Mendeleev Communications, vol. 34, no. 2, Feb. 2024, pp. 279-281. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2024.02.039.

Keywords

2-a]benzimidazol-9-ium salts
aminoazoles
Cyclization
imidazo[1
iodoacetyl azoles
quantum chemical calculations.
transamination

Abstract

N-Iodoacetyl-substituted azoles undergo transfer of iodoacetyl group from heterocyclic N atom toward the amino group of amino azoles, unlike the earlier investigated iodomethyl ketones. The proposed mechanism explaining the observed difference in such transamination is confirmed by calculations. The product derived from 2-aminobenzimidazole is cyclized into fused imidazo[1,2-α]benzimidazol- 9-ium salt.

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