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Communication | Regular issue | Vol 36, No. 10, 1993, pp.2229-2236
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6454
The Regiospecific Synthesis of ortho Aminonaphthophenones via the Addition of Carbanions to Naphthoxazin-4-ones

Weijiang Zhang, Ruiyan Liu, and James M. Cook*

*Department of Chemistry, University of Wisconsin-Milwaukee, Milwaukee, Wisconsin 53201, U.S.A.


The conversion of nitronaphthalenes (see 4a and 4b) into the corresponding ortho aminonaphthylnitriles (5a and 5b) via the process of Tomioka, when combined with the addition of carbanions to the intermediate naphthoxazin-4-ones, provided a route to ortho aminonaphthophenones (7a) and (7b). These key intermediates were employed to synthesize the benzfused 2’-fluoro-1,4-benzodiazepines (1-3).