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Reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with N-arylisoindolines |
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| Authors: | Dietrich Döpp Alaa A Hassan Aboul-Fetouh E Mourad Jörg Rust |
| Institution: | a Organische Chemie, Universität Duisburg-Essen, Essen Campus, D-45117 Essen, Germany b Chemistry Department, Faculty of Science, El Minia University, El Minia 61519, Egypt c Max-Planck-Institut für Kohlenforschung, D-45470 Mülheim/Ruhr, Germany |
| Abstract: | In a multistep reaction, 3,3′-(2-aryl-2H-isoindol-1,3-ylene)-di-(1,4-naphthoquinone-2-carbonitriles) 13a-f have been formed in 25-61% yield from a series of N-arylisoindolines 8a-f with (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile (1) in aerated pyridine. The structure of one of these products (13f) has been unambiguously confirmed by a single crystal X-ray structure analysis. Under otherwise the same conditions, 2-(3-methoxyphenyl)-isoindoline (8g) and 1 gave 38% of 4-(2,3-dihydro-1H-isoindol-2-yl)-2-methoxyphenyl]-1,3-dioxoindan-2-ylidene)acetonitrile (15). Rationales for these conversions involving the known rearrangement of the radical anion of 1 into the radical anion of 1,4-naphthoquinone-2,3-dicarbonitrile (3) are presented. |
| Keywords: | Donor-acceptor interactions 2H-Isoindoles Merocyanines Rearrangement Radical ions X-ray crystal structure analysis |
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