A Direct One-Pot Synthesis of Naphtho[2,3-b]furan-4,9-dione Derivatives via C,O-Dialkylation of β-Dicarbonyl Compounds by 2,3-Dichloro-1,4-naphthoquinones

Hua-You Hu; Ye Zhu; Lei Wang; Jian-Hua Xu

doi:10.1055/s-2005-865305

PAPER

A Direct One-Pot Synthesis of Naphtho[2,3-b]furan-4,9-dione Derivatives via C,O-Dialkylation of β-Dicarbonyl Compounds by 2,3-Dichloro-1,4-naphthoquinones

Hua-You Hu, Ye Zhu, Lei Wang, Jian-Hua Xu*
Department of Chemistry, Nanjing University, Nanjing 210093, P. R. China
Fax: +86(25)83317761; e-Mail: xujh@nju.edu.cn;

Abstract

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Abstract

Base-promoted reactions of acyclic and cyclic β-dicarbonyl compounds (3) with 2,3-dichloro-1,4-naphthoquinone (1) and 4a,6,7,8a-tetrachloro-1,4-methanonaphthalene-5,8-dione (2) resulted in C,O-dialkylation of 3 to give 2,3-disubstituted naphtho[2,3-b]furan-4,9-diones (4) and 5,8-methanonaphtho[2,3-b]furan-4,9-diones (6) respectively in moderate to high yields.

Key words

alkylations - ketones - furans - quinones - cyclizations

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References

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