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5. 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

Author

Lipson, Victoria V, primary, Pavlovska, Tetiana L, additional, Svetlichnaya, Nataliya V, additional, Poryvai, Anna A, additional, Gorobets, Nikolay Yu, additional, Van der Eycken, Erik V, additional, Konovalova, Irina S, additional, Shiskina, Svetlana V, additional, Borisov, Alexander V, additional, Musatov, Vladimir I, additional, and Mazepa, Alexander V, additional

Published
2019
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8. 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.

Author

Lipson VV, Pavlovska TL, Svetlichnaya NV, Poryvai AA, Gorobets NY, Van der Eycken EV, Konovalova IS, Shiskina SV, Borisov AV, Musatov VI, and Mazepa AV

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-5 H -pyrrolo[1,2- c ]imidazol-5-ones and 3-(2-amino-4-aryl-1 H -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.

Published
2019
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