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
Publication type: Journal Article
Publication date: 2023-03-01
scimago Q3
wos Q3
SJR: 0.305
CiteScore: 3.0
Impact factor: 1.7
ISSN: 09599436, 1364551X
General Chemistry
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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Total citations:
9
Citations from 2024:
6
(66.67%)
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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.
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Semenova N. V., Schmidt E. Yu., 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://doi.org/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 V
AU - Schmidt, Elena Yu
AU - Ushakov, I A
AU - Trofimov, Boris A.
PY - 2023
DA - 2023/03/01
PB - OOO Zhurnal "Mendeleevskie Soobshcheniya"
SP - 164-166
IS - 2
VL - 33
SN - 0959-9436
SN - 1364-551X
ER -
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@article{2023_Semenova,
author = {Nadezhda V Semenova and Elena Yu Schmidt and I A Ushakov and Boris A. 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 = {OOO Zhurnal "Mendeleevskie Soobshcheniya"},
month = {mar},
url = {https://doi.org/10.1016/j.mencom.2023.02.005},
number = {2},
pages = {164--166},
doi = {10.1016/j.mencom.2023.02.005}
}
Cite this
MLA
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Semenova, Nadezhda 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, vol. 33, no. 2, Mar. 2023, pp. 164-166. https://doi.org/10.1016/j.mencom.2023.02.005.