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Communication | Regular issue | Vol 38, No. 7, 1994, pp.1453-1457
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6715
Formation of a Strained Triazapentalenoindene Skeleton via the Rearrangement of 2,3-Dihydro-7-nitro-1H-Imidazo[2,1-a]phthalazin-4-ium-6-olate Effected by Dichloroacetic Anhydride

Mónika Fuxreiter, Antal Csámpai,* and János Császár

*Department of Organic Chemistry, Eötvös Loránd University Budapest, H-1518 Budapest 112, P.O.Box 32, Hungary

Abstract

On treatment with dichloroacetic anhydride 2,3-dihydro-7-nitro-1H-imidazo[2,1-a]phthalazin-4-ium-6-olate (5) underwent a backbone rearrangement leading to isoindole derivative (12), which represents a new strained ring system with three condensed five-membered heterocycles. The structure of its stable 3-deacylated form, 3,3a,5a-triaza-1,1-dichloro-1,2,3,3a,4,5,6,6a-octahydro-7-nitropentaleno[3a,3-a]indene-2,6-dione (13) was evidenced by ir, ms, nmr, and X-ray methods.