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Acetylene-driven multi-molecular assemblies of high complexity: imidazo[1,2-a]pyridines and 5-chloro-N-[2-(imidazo[1,2-a]pyridin-6-yl)vinyl]pyridin-2-amine

Nadezhda Victorovna Semenova 1
Nadezhda Victorovna Semenova
, 
Elena Yur'evna Schmidt 1
Elena Yur'evna Schmidt
, 
Igor Alekseevich Ushakov 1
Igor Alekseevich Ushakov
, 
Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
10.1016/j.mencom.2023.02.005
Published 2023-02-13
Communication , Volume 33, Issue 2, 164-166
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Semenova N. V. et al. Acetylene-driven multi-molecular assemblies of high complexity: imidazo[1,2-a]pyridines and 5-chloro-N-[2-(imidazo[1,2-a]pyridin-6-yl)vinyl]pyridin-2-amine // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 164-166.
GOST all authors (up to 50) Copy
Semenova N. V., Schmidt E. Y., Ushakov I. A., Trofimov B. A. Acetylene-driven multi-molecular assemblies of high complexity: imidazo[1,2-a]pyridines and 5-chloro-N-[2-(imidazo[1,2-a]pyridin-6-yl)vinyl]pyridin-2-amine // Mendeleev Communications. 2023. Vol. 33. No. 2. pp. 164-166.
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TY - JOUR
DO - 10.1016/j.mencom.2023.02.005
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.005
TI - Acetylene-driven multi-molecular assemblies of high complexity: imidazo[1,2-a]pyridines and 5-chloro-N-[2-(imidazo[1,2-a]pyridin-6-yl)vinyl]pyridin-2-amine
T2 - Mendeleev Communications
AU - Semenova, Nadezhda Victorovna
AU - Schmidt, Elena Yur'evna
AU - Ushakov, Igor Alekseevich
AU - Trofimov, Boris Aleksandrovich
PY - 2023
DA - 2023/02/13
PB - Mendeleev Communications
SP - 164-166
IS - 2
VL - 33
ER -
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@article{2023_Semenova,
author = {Nadezhda Victorovna Semenova and Elena Yur'evna Schmidt and Igor Alekseevich Ushakov and Boris Aleksandrovich Trofimov},
title = {Acetylene-driven multi-molecular assemblies of high complexity: imidazo[1,2-a]pyridines and 5-chloro-N-[2-(imidazo[1,2-a]pyridin-6-yl)vinyl]pyridin-2-amine},
journal = {Mendeleev Communications},
year = {2023},
volume = {33},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.005},
number = {2},
pages = {164--166},
doi = {10.1016/j.mencom.2023.02.005}
}
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Semenova, Nadezhda Victorovna, et al. “Acetylene-driven multi-molecular assemblies of high complexity: imidazo[1,2-a]pyridines and 5-chloro-N-[2-(imidazo[1,2-a]pyridin-6-yl)vinyl]pyridin-2-amine.” Mendeleev Communications, vol. 33, no. 2, Feb. 2023, pp. 164-166. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2023.02.005.

Keywords

2-aminopyridines
Acetylene
ethynylation
imidazo[1,2-a]pyridines
superbases
vinylation

Abstract

Acetylene reacts with 2-aminopyridines in the superbase system KOBut/DMSO (the initial acetylene pressure ∼8 atm, 80 °C, 5 min) to give 2,3-dimethylimidazo[1,2-α]-pyridines in up to 60% yields. In the case of 2-amino-5-chloropyridine, along with ‘normal’ product, (Z)-5-chloro- N-[2-(2,3-dimethylimidazo[1,2-α]pyridin-6-yl)vinyl]pyridin-2-amine is formed in 40% yield. These multi-molecular assemblies involve parallel nucleophilic addition of N-centered anions to the triple bond and ethynylation of the forming C=N bond.

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