Reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with 
N-arylisoindolines

Döpp, Dietrich; Hassan, Alaa A.; Nour El-Din, Ahmed M.; Mourad, Aboul-Fetouh E.; Lehmann, Christian W.; Rust, Jörg

doi:10.1016/j.tet.2006.09.070

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Reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with N-arylisoindolines

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Lehmann, Christian W.
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Rust, Jörg
Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Döpp, D., Hassan, A. A., Nour El-Din, A. M., Mourad, A.-F.-E., Lehmann, C. W., & Rust, J. (2006). Reaction of (1,3-dioxo-2,3-dihydro-1H-inden-2-ylidene)propanedinitrile with N-arylisoindolines. Tetrahedron, 62(50), 11618-11626. doi:10.1016/j.tet.2006.09.070.

Cite as: https://hdl.handle.net/11858/00-001M-0000-000F-947F-9

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.