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An efficient three-component reaction involving [3 + 1 + 1] furannulation leading to furanonaphthoquinones in water

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Abstract

An efficient and clean green synthesis of highly substituted linear naphtho[2,3-b]-furan-4,9-dione derivatives, starting from 2-hydroxy-1,4-naphthoquinone, alkyl isocyanides and a variety of aldehydes, is described. This new method provides the first example of an efficient regioselective synthetic method for the synthesis of linear naphtho[2,3-b]-furan-4,9-dione ring systems by formation of three bonds. This [3 + 1 + 1] furannulation strategy affords furanonaphthoquinones in moderate to high yields, using water as a cheap, non-toxic, environmentally friendly solvent, in a one-step reaction, without the need of complicated work-up procedures.

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Authors and Affiliations

  1. Petrochemical Department, Iran Polymer and Petrochemical Institute, Tehran, Iran

    Mohammad Bagher Teimouri

  2. Central Laboratory, Iran Polymer and Petrochemical Institute, Tehran, Iran

    Reihaneh Bazhrang

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  1. Mohammad Bagher Teimouri
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  2. Reihaneh Bazhrang
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Correspondence to Mohammad Bagher Teimouri.

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Correspondence: Mohammad Bagher Teimouri, Petrochemical Department, Iran Polymer and Petrochemical Institute, P.O. Box 14965-115, Tehran, Iran.

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Teimouri, M., Bazhrang, R. An efficient three-component reaction involving [3 + 1 + 1] furannulation leading to furanonaphthoquinones in water. Monatsh Chem 139, 957–961 (2008). https://doi.org/10.1007/s00706-007-0846-4

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