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Short Paper | Special issue | Vol 88, No. 1, 2014, pp.705-710
Published online, 8th July, 2013
DOI: 10.3987/COM-13-S(S)25
Two-Directional Synthesis of 2,6-Dimethylpyrrolo[2,3-f]indole-4,8-dione by Double Claisen Rearrangement and Nitrene Cyclization

Andrea Visconti and Christopher J. Moody*

*School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, U.K.

Abstract

Double Claisen rearrangement of the bis-allyl ether of 2,5-dichloro-1,4-hydroquinone, followed by alkene isomerization, oxidation and double chloride displacement with azide gives 2,5-diazido-3,6-dipropenyl-1,4-benzoquinone. Upon heating, a double nitrene cyclization occurs completing a high yielding, two-directional route to the pyrrolo[2,3-f]indole-4,8-dione ring system.