Ring‐Opening of Pyridines with Acylacetylenes and Water: Straightforward Access to 5‐[(Z)‐Acylethenyl]amino‐2,4‐pentadienals
B. A. Trofimov
1
,
Ludmila V. Andriyankova
1
,
Kseniya V Belyaeva
1
,
Lina P. Nikitina
1
,
A.V. Afonin
1
,
Anastasiya G. Mal’kina
1
Publication type: Journal Article
Publication date: 2015-11-19
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Pyridines undergo exceptionally facile ring opening under the action of acylacetylenes (e.g., benzoylphenylacetylene, furoylphenylacetylene, and thenoylphenylacetylene) and water (r.t., with or without KOH) to afford 5-[(Z)-acylethenyl]amino-2,4-pentadienals in 84–92 % yield. The reaction is stereoselective: only the Z configuration for ethenyl substituents and preferentially (85–95 %) the E,E configuration for the 2,4-pentadienal moiety were observed (the second configuration being E,Z). In the cases of 3-methylpyridine and benzoylphenylacetylene, two regioisomers, namely, the corresponding 2-methyl- and 4-methylaminopentadienals, were formed in a 7:3 ratio.
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14
Total citations:
14
Citations from 2024:
3
(21.43%)
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Trofimov B. A. et al. Ring‐Opening of Pyridines with Acylacetylenes and Water: Straightforward Access to 5‐[(Z)‐Acylethenyl]amino‐2,4‐pentadienals // European Journal of Organic Chemistry. 2015. Vol. 2015. No. 36. pp. 7876-7879.
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Trofimov B. A., Andriyankova L. V., Belyaeva K. V., Nikitina L. P., Afonin A., Mal’kina A. G. Ring‐Opening of Pyridines with Acylacetylenes and Water: Straightforward Access to 5‐[(Z)‐Acylethenyl]amino‐2,4‐pentadienals // European Journal of Organic Chemistry. 2015. Vol. 2015. No. 36. pp. 7876-7879.
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RIS
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TY - JOUR
DO - 10.1002/ejoc.201501286
UR - https://doi.org/10.1002/ejoc.201501286
TI - Ring‐Opening of Pyridines with Acylacetylenes and Water: Straightforward Access to 5‐[(Z)‐Acylethenyl]amino‐2,4‐pentadienals
T2 - European Journal of Organic Chemistry
AU - Trofimov, B. A.
AU - Andriyankova, Ludmila V.
AU - Belyaeva, Kseniya V
AU - Nikitina, Lina P.
AU - Afonin, A.V.
AU - Mal’kina, Anastasiya G.
PY - 2015
DA - 2015/11/19
PB - Wiley
SP - 7876-7879
IS - 36
VL - 2015
SN - 1434-193X
SN - 1099-0690
ER -
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BibTex (up to 50 authors)
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@article{2015_Trofimov,
author = {B. A. Trofimov and Ludmila V. Andriyankova and Kseniya V Belyaeva and Lina P. Nikitina and A.V. Afonin and Anastasiya G. Mal’kina},
title = {Ring‐Opening of Pyridines with Acylacetylenes and Water: Straightforward Access to 5‐[(Z)‐Acylethenyl]amino‐2,4‐pentadienals},
journal = {European Journal of Organic Chemistry},
year = {2015},
volume = {2015},
publisher = {Wiley},
month = {nov},
url = {https://doi.org/10.1002/ejoc.201501286},
number = {36},
pages = {7876--7879},
doi = {10.1002/ejoc.201501286}
}
Cite this
MLA
Copy
Trofimov, B. A., et al. “Ring‐Opening of Pyridines with Acylacetylenes and Water: Straightforward Access to 5‐[(Z)‐Acylethenyl]amino‐2,4‐pentadienals.” European Journal of Organic Chemistry, vol. 2015, no. 36, Nov. 2015, pp. 7876-7879. https://doi.org/10.1002/ejoc.201501286.