1172730-73-2Relevant academic research and scientific papers
Reactions of 2′-oxo-1′,2′-dihydrospiro[cyclopropane-1, 3′-indole]-2,2,3,3-tetracarbonitriles with nucleophiles
Kayukov, Ya. S.,Kayukova,Kalyagina,Bardasov,Ershov,Nasakin,Tafeenko
experimental part, p. 392 - 401 (2011/06/21)
2′-Oxo-1′,2′-dihydrospiro[cyclopropane-1,3′-indole] -2,2,3,3-tetracarbonitriles reacted with oxygencentered nucleophiles to form addition products at the cyano groups with conservation of the three-membered ring. Reactions of the title compounds with alcohols required the presence of base catalyst, and the products, 2-amino-4,4-dialkoxy-2′-oxo-1′, 2′-dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1, 5-dicarbonitriles, were converted into the corresponding 2-imino-2′,4- dioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1,5-dicarbonitriles and 2,2′,4-trioxospiro[3-azabicyclo[3.1.0]hexane-6,3′-indole]-1, 5-dicarbonitriles by the action of acetic and sulfuric acids, respectively. The reactions with ketone oximes occurred in the absence of a catalyst, yielding 2-amino-4,4-bis(alkylideneaminooxy)-2′-oxo-1′,2′- dihydrospiro[3-azabicyclo[3.1.0]hex-2-ene-6,3′-indole]-1, 5-dicarbonitriles. The reactions with thiols, aliphatic amines, and anilines were accompanied by opening of the three-membered ring. In the reactions with triphenylphosphine and thiols 2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene) malononitrile was obtained, while morpholine and N,N-dimethylaniline gave rise, respectively, to 3,3-diaryl-and 3,3-dimorpholino-1H-indol-2(3H)-ones and tri- and dicyanoethylene derivatives.
