Synthesis of Benzo[b]naphtho[2,3-d]furan-6,11-dione via One-pot Remote Anionic Fries Rearrangement and Metalation Reaction

Mariangela S. Azevedo; Glaucia B. C. Alves; Jari N. Cardoso; Rosangela S. C. Lopes; Claudio C. Lopes

doi:10.1055/s-2004-822357

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Synthesis 2004(8): 1262-1268
DOI: 10.1055/s-2004-822357

PAPER

Synthesis of Benzo[b]naphtho[2,3-d]furan-6,11-dione via One-pot Remote Anionic Fries Rearrangement and Metalation Reaction

Mariangela S. Azevedo^a, Glaucia B. C. Alves^a, Jari N. Cardoso^b, Rosangela S. C. Lopes^b, Claudio C. Lopes*^b
^a Instituto de Química, Departamento de Química Orgânica, CT, Universidade Federal do Rio de Janeiro, Bl A, 6o andar, Rio de Janeiro, RJ, CEP21949 900, Brazil
^b Instituto de Química, Departamento de Química Analítica, CT, Universidade Federal do Rio de Janeiro, Bl A, 5o andar, Rio de Janeiro, RJ, CEP21949 900, Brazil
e-Mail: claudiosabbatini@uol.com.br;

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Publication History

Received 26 March 2003
Publication Date:
28 April 2004 (online)

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Abstract

The use of a lithiation reaction to transform the bromo-arylcarbamate 8a into the corresponding benzo[b]naphtho[2,3-d]furan-6,11-dione (2) is described.

Keywords

brazanquinones - metalation - tetracyclic - Fries rearrangement - synthesis

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