Regiospecific Synthesis of Benzo[b]fluorenones via Ring Contraction by Benzil-Benzilic Acid Rearrangement of Benz[a]anthracene-5,6-diones

Asit Patra; Sujit K. Ghorai; Saroj R. De; Dipakranjan Mal

doi:10.1055/s-2006-942468

PAPER

Regiospecific Synthesis of Benzo[b]fluorenones via Ring Contraction by Benzil-Benzilic Acid Rearrangement of Benz[a]anthracene-5,6-diones

Asit Patra, Sujit K. Ghorai, Saroj R. De, Dipakranjan Mal*
Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India
e-Mail: dmal@chem.iitkgp.ernet.in;

Abstract

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Abstract

A regiospecific route to benzo[b]fluorenones is described. The synthesis is based upon a one-pot, regiospecific benzannulation of 1,4-dipolar synthons with naphthoquinone monoketal and ring contraction of the generated benz[a]anthracene-5,6-diones through benzil-benzilic acid rearrangement.

Key words

1,4-dipolar synthons - benz[a]anthracene-5,6-diones - benzo[b]fluorenones - benzannulation - benzil-benzilic acid rearrangement

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References

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