TY - JOUR A1 - Lipson, Victoria V. A1 - Pavlovska, Tetiana L. A1 - Svetlichnaya, Nataliya V. A1 - Poryvai, Anna A. A1 - Gorobets, Nikolay Yu. A1 - Van der Eycken, Erik V. A1 - Konovalova, Irina S. A1 - Shiskina, Svetlana V. A1 - Borisov, Alexander V. A1 - Musatov, Vladimir I. A1 - Mazepa, Alexander V. T1 - 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 JF - Beilstein Journal of Organic Chemistry PY - 2019/// VL - 15 SP - 1032 EP - 1045 SN - 1860-5397 DO - 10.3762/bjoc.15.101 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.15.101 KW - 2-amino-4-arylimidazole KW - (2-amino-4-arylimidazolyl)propanoic acid KW - isatin KW - Meldrum’s acid KW - multicomponent reactions KW - pyrrolo[1,2-c]imidazole KW - 3,3’-spirooxindoles N2 - 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. ER -