Semistabilized Diazatrienyl Anions from Pyridine Imines and Acetylenes: An Access to (Z)-Stilbene/Imidazopyridine Ensembles, Benzyl Imidazopyridines, and Beyond
Ivan A Bidusenko
1
,
Elena Yu. Schmidt
1
,
Igor A. Ushakov
1
,
Alexander V. Vashchenko
1
,
Nadezhda I Protsuk
1
,
Vladimir B Orel
1, 2
,
Publication type: Journal Article
Publication date: 2022-08-31
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
36044622
Organic Chemistry
Abstract
Semistabilized diazatrienyl anions are generated by the reaction of 2-pyridylarylimines with arylacetylenes in superbase systems MOtBu (M = Li, Na, K)/DMSO at ambient temperature for 15 min. The initial intermediate N-centered propargyl-1,3-diaza-1,3,5-trienyl anions undergo intermolecular cyclization to benzyl imidazopyridine anions (formally [3 + 2] cycloaddition), further intercepting a second molecule of the starting pyridylimines or a proton of medium to afford (Z)-stilbene/imidazopyridine ensembles and benzyl imidazopyridines. The charge distribution in all intermediate anions and their synthetic evolution are consistent with quantum-chemical analysis (B2PLYPD/6-311+G**//B3LYP/6-31+G*).
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Total citations:
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Citations from 2024:
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(35.71%)
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Bidusenko I. A. et al. Semistabilized Diazatrienyl Anions from Pyridine Imines and Acetylenes: An Access to (Z)-Stilbene/Imidazopyridine Ensembles, Benzyl Imidazopyridines, and Beyond // Journal of Organic Chemistry. 2022. Vol. 87. No. 18. pp. 12225-12239.
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Bidusenko I. A., Schmidt E. Y., Ushakov I. A., Vashchenko A. V., Protsuk N. I., Orel V. B., Vitkovskaya N., Trofimov B. A. Semistabilized Diazatrienyl Anions from Pyridine Imines and Acetylenes: An Access to (Z)-Stilbene/Imidazopyridine Ensembles, Benzyl Imidazopyridines, and Beyond // Journal of Organic Chemistry. 2022. Vol. 87. No. 18. pp. 12225-12239.
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TY - JOUR
DO - 10.1021/acs.joc.2c01372
UR - https://doi.org/10.1021/acs.joc.2c01372
TI - Semistabilized Diazatrienyl Anions from Pyridine Imines and Acetylenes: An Access to (Z)-Stilbene/Imidazopyridine Ensembles, Benzyl Imidazopyridines, and Beyond
T2 - Journal of Organic Chemistry
AU - Bidusenko, Ivan A
AU - Schmidt, Elena Yu.
AU - Ushakov, Igor A.
AU - Vashchenko, Alexander V.
AU - Protsuk, Nadezhda I
AU - Orel, Vladimir B
AU - Vitkovskaya, Nadezhda
AU - Trofimov, B. A.
PY - 2022
DA - 2022/08/31
PB - American Chemical Society (ACS)
SP - 12225-12239
IS - 18
VL - 87
PMID - 36044622
SN - 0022-3263
SN - 1520-6904
ER -
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BibTex (up to 50 authors)
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@article{2022_Bidusenko,
author = {Ivan A Bidusenko and Elena Yu. Schmidt and Igor A. Ushakov and Alexander V. Vashchenko and Nadezhda I Protsuk and Vladimir B Orel and Nadezhda Vitkovskaya and B. A. Trofimov},
title = {Semistabilized Diazatrienyl Anions from Pyridine Imines and Acetylenes: An Access to (Z)-Stilbene/Imidazopyridine Ensembles, Benzyl Imidazopyridines, and Beyond},
journal = {Journal of Organic Chemistry},
year = {2022},
volume = {87},
publisher = {American Chemical Society (ACS)},
month = {aug},
url = {https://doi.org/10.1021/acs.joc.2c01372},
number = {18},
pages = {12225--12239},
doi = {10.1021/acs.joc.2c01372}
}
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MLA
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Bidusenko, Ivan A., et al. “Semistabilized Diazatrienyl Anions from Pyridine Imines and Acetylenes: An Access to (Z)-Stilbene/Imidazopyridine Ensembles, Benzyl Imidazopyridines, and Beyond.” Journal of Organic Chemistry, vol. 87, no. 18, Aug. 2022, pp. 12225-12239. https://doi.org/10.1021/acs.joc.2c01372.
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