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Paper | Special issue | Vol 37, No. 3, 1994, pp.1603-1613
Published online, 1st January, 1970
DOI: 10.3987/COM-93-S124
On the Reduction of vic-Dioxopyrrolo[2,3-b]indoles with Lithium Aluminum Hydride

Gert Kollenz* and Chang He Xi

*Institute of Organic Chemistry, Karl-Franzens-University Graz, Heinrichstr. 28, A-8010 Graz, Austria

Abstract

Dioxopyrrol[2,3-b]indoles and their structural analogues, diaza[n,3,3]propellanediones were reduced by lithium aluminum hydride affording their hydrogenated derivatives (1) and (2), each of them representing a mixture of diastereomers. Under equal reaction conditions an open-chain compound (3) was obtained by reduction of 2,3-dioxo-8,8a-diphenyl-1,2,8,8a-tetrahydropyrrolo[2,3-b]indole. 3 cyclizes with oxalyl chloride affording 4. Under acidic conditions 1 and 2 could be decomposed to the indole derivatives (5) and (6), respectively.