Synthesis of 4,5-substituted methyl 1H-pyrrole-2-carboxylates from 3-chloroacrylaldehydes and hippuric acid
Alexander S. Fisyuk
1, 2
,
Anna L. Samsonenko
1, 2
,
Anastasia S. Kostyuchenko
1, 2
,
Tatyana Yu. Zheleznova
1, 2
,
Vladislav Yu. Shuvalov
1, 2
,
Evgenii B. Uliankin
1, 2
,
Publication type: Journal Article
Publication date: 2024-03-27
scimago Q2
wos Q2
SJR: 0.559
CiteScore: 4.6
Impact factor: 2.3
ISSN: 00397881, 1437210X
Abstract
The Vilsmeier–Haack reaction of ketones with DMF and POCl3 produced 3-chloroacrylcarbaldehydes, which were converted into the corresponding (Z)-4-[(Z)- or (Z)-4-[(E)-3-chloroallylidene)-2-phenyloxazol-5(4H)-ones] (azlactones) or their isomeric mixtures when heated with hippuric acid in propionic anhydride. It was shown that the alcoholysis products of these compounds, resulting from the opening of the oxazolone ring, undergo copper-catalyzed intramolecular cross-coupling reactions with the formation of methyl 1H-pyrrole-2-carboxylates. Thus, a one-pot method was developed for the synthesis of methyl 1H-pyrrole-2-carboxylates starting from 4-(3-chloroallylidene)-2-phenyloxazol-5(4H)-ones.
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Total citations:
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Citations from 2024:
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(100%)
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Fisyuk A. S. et al. Synthesis of 4,5-substituted methyl 1H-pyrrole-2-carboxylates from 3-chloroacrylaldehydes and hippuric acid // Synthesis. 2024. Vol. 56. No. 15. pp. 2423-2431.
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Fisyuk A. S., Samsonenko A. L., Kostyuchenko A. S., Zheleznova T. Y., Shuvalov V. Y., Uliankin E. B., Shatsauskas A. L. Synthesis of 4,5-substituted methyl 1H-pyrrole-2-carboxylates from 3-chloroacrylaldehydes and hippuric acid // Synthesis. 2024. Vol. 56. No. 15. pp. 2423-2431.
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TY - JOUR
DO - 10.1055/a-2295-8544
UR - http://www.thieme-connect.de/DOI/DOI?10.1055/a-2295-8544
TI - Synthesis of 4,5-substituted methyl 1H-pyrrole-2-carboxylates from 3-chloroacrylaldehydes and hippuric acid
T2 - Synthesis
AU - Fisyuk, Alexander S.
AU - Samsonenko, Anna L.
AU - Kostyuchenko, Anastasia S.
AU - Zheleznova, Tatyana Yu.
AU - Shuvalov, Vladislav Yu.
AU - Uliankin, Evgenii B.
AU - Shatsauskas, Anton L.
PY - 2024
DA - 2024/03/27
PB - Georg Thieme Verlag KG
SP - 2423-2431
IS - 15
VL - 56
SN - 0039-7881
SN - 1437-210X
ER -
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BibTex (up to 50 authors)
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@article{2024_Fisyuk,
author = {Alexander S. Fisyuk and Anna L. Samsonenko and Anastasia S. Kostyuchenko and Tatyana Yu. Zheleznova and Vladislav Yu. Shuvalov and Evgenii B. Uliankin and Anton L. Shatsauskas},
title = {Synthesis of 4,5-substituted methyl 1H-pyrrole-2-carboxylates from 3-chloroacrylaldehydes and hippuric acid},
journal = {Synthesis},
year = {2024},
volume = {56},
publisher = {Georg Thieme Verlag KG},
month = {mar},
url = {http://www.thieme-connect.de/DOI/DOI?10.1055/a-2295-8544},
number = {15},
pages = {2423--2431},
doi = {10.1055/a-2295-8544}
}
Cite this
MLA
Copy
Fisyuk, Alexander S., et al. “Synthesis of 4,5-substituted methyl 1H-pyrrole-2-carboxylates from 3-chloroacrylaldehydes and hippuric acid.” Synthesis, vol. 56, no. 15, Mar. 2024, pp. 2423-2431. http://www.thieme-connect.de/DOI/DOI?10.1055/a-2295-8544.