Springer Nature
Chemistry of Heterocyclic Compounds
,  volume 58 ,  issue 8-9 ,  pages 421-431

A Three-Component Synthesis of trifluoromethylated hexahydropyrrolo[1,2-a]imidazol-5-ones and hexahydropyrrolo[1,2-a]pyrimidin-6-ones

Publication type: Journal Article
Publication date: 2022-09-01
Springer Nature
scimago Q4
wos Q4
SJR: 0.243
CiteScore: 2.7
Impact factor: 1.0
ISSN: 00093122, 15738353
Organic Chemistry
Abstract
A three-component reaction of ethyl trifluoropyruvate, methyl ketones, and ethylenediamine or 1,3-diaminopropane afforded hexahydropyrrolo[1,2-a]imidazol-5-ones and hexahydropyrrolo[1,2-a]pyrimidin-6-ones. When using an excess of ethyl trifluoropyruvate in reactions with acetone and diamines, dipyrrolo[1,2-a:2',1'-b]imidazole-3,8-dione and dipyrrolo[1,2-a:2',1'-b]pyrimidine-3,9-dione were obtained. An aldol mechanism for the formation of the bi- and tricyclic compounds was proposed, and their diastereomeric structure was established. Some of the obtained heterocycles were found to possess analgesic activity.
Found 
Found 
3 citations
Goryaeva Marina
PhD in Chemistry
55 publications,  527 citations
h-index: 14
Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences
Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences
1 citation
Triandafilova Galina
23 publications,  177 citations
h-index: 10
Perm National Research Polytechnic University
Perm National Research Polytechnic University
Institute of Ecology and Genetics of Microorganisms of the Ural Branch of the Russian Academy of Sciences
Institute of Ecology and Genetics of Microorganisms of the Ural Branch of the Russian Academy of Sciences
Research interests
Antioxidants
Microbiology
1 citation
Kodess Mikhail
PhD
298 publications,  2 854 citations
h-index: 25
Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences
Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences
Research interests
NMR spectroscopy
1 citation
Kushch Svetlana
PhD in Chemistry
16 publications,  110 citations
h-index: 7
Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences
Postovsky Institute of Organic Synthesis of the Ural Branch of the Russian Academy of Sciences

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Goryaeva M. V. et al. A Three-Component Synthesis of trifluoromethylated hexahydropyrrolo[1,2-a]imidazol-5-ones and hexahydropyrrolo[1,2-a]pyrimidin-6-ones // Chemistry of Heterocyclic Compounds. 2022. Vol. 58. No. 8-9. pp. 421-431.
GOST all authors (up to 50) Copy
Goryaeva M. V., Fefelova O. А., Burgart Y. V., Ezhikova M. А., Kodess M. I., Slepukhin P. А., Triandafilova G. А., Solodnikov S. Yu., Krasnykh O. P., Saloutin V. I. A Three-Component Synthesis of trifluoromethylated hexahydropyrrolo[1,2-a]imidazol-5-ones and hexahydropyrrolo[1,2-a]pyrimidin-6-ones // Chemistry of Heterocyclic Compounds. 2022. Vol. 58. No. 8-9. pp. 421-431.
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RIS Copy
TY - JOUR
DO - 10.1007/s10593-022-03108-4
UR - https://doi.org/10.1007/s10593-022-03108-4
TI - A Three-Component Synthesis of trifluoromethylated hexahydropyrrolo[1,2-a]imidazol-5-ones and hexahydropyrrolo[1,2-a]pyrimidin-6-ones
T2 - Chemistry of Heterocyclic Compounds
AU - Goryaeva, Marina V
AU - Fefelova, Olesya А
AU - Burgart, Yanina V.
AU - Ezhikova, Marina А
AU - Kodess, Mikhail I.
AU - Slepukhin, Pavel А
AU - Triandafilova, Galina А
AU - Solodnikov, Sergey Yu
AU - Krasnykh, Olga P
AU - Saloutin, Victor I.
PY - 2022
DA - 2022/09/01
PB - Springer Nature
SP - 421-431
IS - 8-9
VL - 58
SN - 0009-3122
SN - 1573-8353
ER -
BibTex |
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BibTex (up to 50 authors) Copy
@article{2022_Goryaeva,
author = {Marina V Goryaeva and Olesya А Fefelova and Yanina V. Burgart and Marina А Ezhikova and Mikhail I. Kodess and Pavel А Slepukhin and Galina А Triandafilova and Sergey Yu Solodnikov and Olga P Krasnykh and Victor I. Saloutin},
title = {A Three-Component Synthesis of trifluoromethylated hexahydropyrrolo[1,2-a]imidazol-5-ones and hexahydropyrrolo[1,2-a]pyrimidin-6-ones},
journal = {Chemistry of Heterocyclic Compounds},
year = {2022},
volume = {58},
publisher = {Springer Nature},
month = {sep},
url = {https://doi.org/10.1007/s10593-022-03108-4},
number = {8-9},
pages = {421--431},
doi = {10.1007/s10593-022-03108-4}
}
MLA
Cite this
MLA Copy
Goryaeva, Marina V., et al. “A Three-Component Synthesis of trifluoromethylated hexahydropyrrolo[1,2-a]imidazol-5-ones and hexahydropyrrolo[1,2-a]pyrimidin-6-ones.” Chemistry of Heterocyclic Compounds, vol. 58, no. 8-9, Sep. 2022, pp. 421-431. https://doi.org/10.1007/s10593-022-03108-4.