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
Lipson, V.V.; Pavlovska, T.L.; Svetlichnaya, N.V.; Poryvai, A.A.; Gorobets, N.Y.; Van der Eycken, E.V.; Konovalova, I.S.; Shiskina, S.V.; Borisov, A.V.; Musatov, V.I.; Mazepa, A.V. (2019). 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 15: 1032-1045. https://dx.doi.org/10.3762/bjoc.15.101
In: Beilstein Journal of Organic Chemistry: Frankfurt. e-ISSN 1860-5397, more
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| Keyword |
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| Author keywords |
2-amino-4-arylimidazole; (2-amino-4-arylimidazolyl)propanoic acid;isatin; Meldrum's acid; multicomponent reactions;pyrrolo[1,2-c]imidazole; 3,3 '-spirooxindoles |
| Authors | | Top |
- Lipson, V.V.
- Pavlovska, T.L.
- Svetlichnaya, N.V.
- Poryvai, A.A.
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- Gorobets, N.Y.
- Van der Eycken, E.V.
- Konovalova, I.S.
- Shiskina, S.V.
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- Borisov, A.V.
- Musatov, V.I.
- Mazepa, A.V.
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| 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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