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Dehydrohalogenation of isomeric 2- and 3-bromomethyl substituted 2,3-dihydrooxazolo[3,2-a]pyridines

Evgenii Veniaminovich Babaev 1
Evgenii Veniaminovich Babaev
, 
Yaroslav Igorevich Koval 1
Yaroslav Igorevich Koval
, 
Viktor Borisovich Rybakov 1
Viktor Borisovich Rybakov
10.1016/j.mencom.2020.03.033
Published 2020-03-02
Communication , Volume 30, Issue 2, 228-230
2
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Babaev E. V., Koval Y. I., Rybakov V. B. Dehydrohalogenation of isomeric 2- and 3-bromomethyl substituted 2,3-dihydrooxazolo[3,2-a]pyridines // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 228-230.
GOST all authors (up to 50) Copy
Babaev E. V., Koval Y. I., Rybakov V. B. Dehydrohalogenation of isomeric 2- and 3-bromomethyl substituted 2,3-dihydrooxazolo[3,2-a]pyridines // Mendeleev Communications. 2020. Vol. 30. No. 2. pp. 228-230.
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TY - JOUR
DO - 10.1016/j.mencom.2020.03.033
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.033
TI - Dehydrohalogenation of isomeric 2- and 3-bromomethyl substituted 2,3-dihydrooxazolo[3,2-a]pyridines
T2 - Mendeleev Communications
AU - Babaev, Evgenii Veniaminovich
AU - Koval, Yaroslav Igorevich
AU - Rybakov, Viktor Borisovich
PY - 2020
DA - 2020/03/02
PB - Mendeleev Communications
SP - 228-230
IS - 2
VL - 30
ER -
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@article{2020_Babaev,
author = {Evgenii Veniaminovich Babaev and Yaroslav Igorevich Koval and Viktor Borisovich Rybakov},
title = {Dehydrohalogenation of isomeric 2- and 3-bromomethyl substituted 2,3-dihydrooxazolo[3,2-a]pyridines},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.033},
number = {2},
pages = {228--230},
doi = {10.1016/j.mencom.2020.03.033}
}
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Babaev, Evgenii Veniaminovich, et al. “Dehydrohalogenation of isomeric 2- and 3-bromomethyl substituted 2,3-dihydrooxazolo[3,2-a]pyridines.” Mendeleev Communications, vol. 30, no. 2, Mar. 2020, pp. 228-230. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.03.033.

Keywords

oxazoles
oxazolo[3,2-a]pyridinium
ring opening
tautomerism
X-ray diffraction

Abstract

3-(Bromomethyl)dihydrooxazolo[3,2-a]pyridinium bromide under the action of base gives stable non-aromatic methylidene structure which can be converted into aromatic oxazolopyridinium cation only under the action of a superacid. On the contrary, 2-bromomethyl isomer under the same conditions affords only aromatic cation. The structure of the products was confirmed by X-ray diffraction.

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