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Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile
Publication type: Journal Article
Publication date: 2022-12-03
PubMed ID:
36500621
Organic Chemistry
Drug Discovery
Physical and Theoretical Chemistry
Pharmaceutical Science
Molecular Medicine
Analytical Chemistry
Chemistry (miscellaneous)
Abstract
An efficient method for the synthesis of pharmaceutically and high-tech prospective 2-(3-amino-2,4-dicyanophenyl)pyrroles (in up to 88% yield) via the reaction of easily available substituted acylethynylpyrroles with malononitrile has been developed. The reaction proceeds in the KOH/MeCN system at 0 °C for 2 h. In the case of 2-acylethynylpyrroles without substituents in the pyrrole ring, the reaction changes direction: instead of the target 2-(3-amino-2,4-dicyanophenyl)pyrroles, the unexpected formation of pyrrolyldienols and products of their intramolecular cyclization, 3-amino-1-acylethylidene-2-cyanopyrrolizines, is observed.
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Gotsko M. D. et al. Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile // Molecules. 2022. Vol. 27. No. 23. p. 8528.
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Gotsko M. D., Saliy I. V., Ushakov I. A., Sobenina L. N., Trofimov B. A. Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile // Molecules. 2022. Vol. 27. No. 23. p. 8528.
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TY - JOUR
DO - 10.3390/molecules27238528
UR - https://doi.org/10.3390/molecules27238528
TI - Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile
T2 - Molecules
AU - Gotsko, Maxim D
AU - Saliy, Ivan V
AU - Ushakov, Igor A.
AU - Sobenina, Lyubov N.
AU - Trofimov, Boris A.
PY - 2022
DA - 2022/12/03
PB - MDPI
SP - 8528
IS - 23
VL - 27
PMID - 36500621
SN - 1420-3049
ER -
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@article{2022_Gotsko,
author = {Maxim D Gotsko and Ivan V Saliy and Igor A. Ushakov and Lyubov N. Sobenina and Boris A. Trofimov},
title = {Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile},
journal = {Molecules},
year = {2022},
volume = {27},
publisher = {MDPI},
month = {dec},
url = {https://doi.org/10.3390/molecules27238528},
number = {23},
pages = {8528},
doi = {10.3390/molecules27238528}
}
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MLA
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Gotsko, Maxim D., et al. “Substituent-Dependent Divergent Synthesis of 2-(3-Amino-2,4-dicyanophenyl)pyrroles, Pyrrolyldienols and 3-Amino-1-acylethylidene-2-cyanopyrrolizines via Reaction of Acylethynylpyrroles with Malononitrile.” Molecules, vol. 27, no. 23, Dec. 2022, p. 8528. https://doi.org/10.3390/molecules27238528.