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Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds
Victoria V. Lipson
1
,
Tetiana L Pavlovska
1
,
Nataliya V Svetlichnaya
2
,
Anna Poryvai
3
,
Nikolay Yu. Gorobets
1
,
Nandini Sharma
4
,
Irina S. Konovalova
1
,
Alexandr B. Borisov
5
,
Vladimir I Musatov
1
,
Alexander V Mazepa
6
1
SSI Institute for Single Crystals of National Academy of Sciences of Ukraine, Nauky Ave. 60, Kharkiv 61074, Ukraine.
|
2
Antidiabetic Drug Laboratory, SI V.Ya. Danilevsky Institute for Endocrine Pathology Problems, Academy of Medical Sciences of Ukraine, 10, Alchevskih St., Kharkiv 61002, Ukraine.
|
3
Chemistry Department, V.N. Karazin Kharkov National University, Kharkov 61022, Ukraine.
|
5
Enamine Ltd., 23 Chervonotkats'ka str., Kyiv 01003, Ukraine.
|
6
A.V. Bogatsky physico-chemical institute of the National Academy of Sciences of Ukraine, 86, Lustdorfskaya doroga, 65080, Odessa, Ukraine.
|
Publication type: Journal Article
Publication date: 2019-05-06
scimago Q2
wos Q3
SJR: 0.482
CiteScore: 3.8
Impact factor: 2.1
ISSN: 18605397
PubMed ID:
31164941
Organic Chemistry
Abstract
The unexpectedly uncatalyzed reaction between 2-amino-4-arylimidazoles, aromatic aldehydes and Meldrum’s acid has selectively led to the corresponding Knoevenagel–Michael adducts containing a free amino group in the imidazole fragment. The adducts derived from Meldrum’s acid have been smoothly converted into 1,7-diaryl-3-amino-6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-5-ones and 3-(2-amino-4-aryl-1H-imidazol-5-yl)-3-arylpropanoic acids. The interaction of 2-amino-4-arylimidazoles with aromatic aldehydes or isatins and acyclic methylene active compounds has led to the formation of pyrrolo[1,2-c]imidazole-6-carbonitriles, pyrrolo[1,2-с]imidazole-6-carboxylates and spiro[indoline-3,7'-pyrrolo[1,2-c]imidazoles], which can be considered as the analogues of both 3,3’-spirooxindole and 2-aminoimidazole marine sponge alkaloids.
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Lipson V. V. et al. Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds // Beilstein Journal of Organic Chemistry. 2019. Vol. 15. pp. 1032-1045.
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Lipson V. V., Pavlovska T. L., Svetlichnaya N. V., Poryvai A., Gorobets N. Y., Sharma N., Konovalova I. S., Shishkina S. V., Borisov A. B., Musatov V. I., Mazepa A. V. Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds // Beilstein Journal of Organic Chemistry. 2019. Vol. 15. pp. 1032-1045.
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TY - JOUR
DO - 10.3762/bjoc.15.101
UR - https://doi.org/10.3762/bjoc.15.101
TI - Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds
T2 - Beilstein Journal of Organic Chemistry
AU - Lipson, Victoria V.
AU - Pavlovska, Tetiana L
AU - Svetlichnaya, Nataliya V
AU - Poryvai, Anna
AU - Gorobets, Nikolay Yu.
AU - Sharma, Nandini
AU - Konovalova, Irina S.
AU - Shishkina, Svitlana V.
AU - Borisov, Alexandr B.
AU - Musatov, Vladimir I
AU - Mazepa, Alexander V
PY - 2019
DA - 2019/05/06
PB - Beilstein-Institut
SP - 1032-1045
VL - 15
PMID - 31164941
SN - 1860-5397
ER -
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BibTex (up to 50 authors)
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@article{2019_Lipson,
author = {Victoria V. Lipson and Tetiana L Pavlovska and Nataliya V Svetlichnaya and Anna Poryvai and Nikolay Yu. Gorobets and Nandini Sharma and Irina S. Konovalova and Svitlana V. Shishkina and Alexandr B. Borisov and Vladimir I Musatov and Alexander V Mazepa},
title = {Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds},
journal = {Beilstein Journal of Organic Chemistry},
year = {2019},
volume = {15},
publisher = {Beilstein-Institut},
month = {may},
url = {https://doi.org/10.3762/bjoc.15.101},
pages = {1032--1045},
doi = {10.3762/bjoc.15.101}
}