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Facile synthesis of spiro[benzo[e]indole-2,2′-piperidine] derivatives and their transformation to novel fluorescent scaffolds |
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| Authors: | Vida Buinauskait? Vytas MartynaitisSven Mangelinckx Gediminas KreizaNorbert De Kimpe Algirdas Ša?kus |
| Institution: | a Institute of Synthetic Chemistry, Kaunas University of Technology, Radvil?n? pl. 19, LT-50254 Kaunas, Lithuania b Department of Organic Chemistry, Faculty of Chemical Technology, Kaunas University of Technology, Radvil?n? pl. 19, LT-50254 Kaunas, Lithuania c Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium d Institute of Applied Research, Vilnius University, Saul?tekio 9-III, LT-10222 Vilnius, Lithuania |
| Abstract: | The reaction of azaheterocyclic enamines with acrylamide was employed for the preparation of novel fluorescent scaffolds possessing a benzoe]indoline moiety. Reaction of 3-substituted 2-methylidene-1H-benzoe]indole with acrylamide gave rise to spirobenzoe]indole-2,2′-piperidin]-6′-ones. Ring opening reactions of the latter spiro compounds were investigated. Benzoe]indoline derivatives possessing 2-(3-carbamoylpropyl), 2-3-(ethoxycarbonyl)propyl] and 2-(4-aminobutyl) side chains were synthesised. The optical properties of the benzoe]indoline derivatives were studied by UV-vis and fluorescence spectroscopy. |
| Keywords: | Benzo[e]indolines Heterocyclic enamines Acrylamide Spiro[benzo[e]indole-2 2&prime -piperidine] Fluorescence |
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