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Benzofuran

Heterocyclic compound consisting of fused benzene and furan rings

Benzofuran
Summary

Heterocyclic compound consisting of fused benzene and furan rings

the heterocyclic chemical compound

Coumarone Benzo[b]furan

Benzofuran is the heterocyclic compound consisting of fused benzene and furan rings. This colourless liquid is a component of coal tar. Benzofuran is the structural nucleus (parent compound) of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants.

There are benzofuran based herbicides: ethofumesate and benfuresate. Several psychoactive drugs such as 5-MAPB and 6-APB are also derived from benzofuran.

Production

Benzofuran is extracted from coal tar. It is also obtained by dehydrogenation of 2-ethylphenol.

Laboratory methods

Benzofurans can be prepared by various methods in the laboratory. Notable examples include:

  • O-alkylation of salicylaldehyde with chloroacetic acid followed by dehydration (cyclication) of the resulting ether and decarboxylation.

  • Perkin rearrangement, where a coumarin is reacted with a hydroxide: :[[Image:Perkin rearrangement.svg|class=skin-invert-image|Perkin rearrangement|450px]]

  • Diels–Alder reaction of nitro vinyl furans with various dienophiles: :[[Image:Benzofuran synthesis via a Diels-Alder reaction on vinyl furans.png|class=skin-invert-image|Diels–Alder reaction yielding a substituted benzofuran|450px]]

  • Cycloisomerization of alkyne ortho-substituted phenols: :[[Image:Benzofurans via Cycloisomerization of Alkynes.png|class=skin-invert-image|Benzofurans via Cycloisomerization|400px]]

References

References

  1. (2014). "Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)". [[Royal Society of Chemistry.
  2. "Classification of herbicides".
  3. {{cite encyclopedia. (2007). Wiley-VCH
  4. Burgstahler, A. W.. (1966). "Coumarone".
  5. Perkin, W. H.. (1870). "XXIX. On some New Bromine Derivatives of Coumarin". [[Journal of the Chemical Society]].
  6. Perkin, W. H.. (1871). "IV. On some New Derivatives of Coumarin". [[Journal of the Chemical Society]].
  7. (1998). "Reactions of Carbonyl Compounds in Basic Solutions. Part 32. The Perkin Rearrangement". [[Journal of the Chemical Society, Perkin Transactions 2]].
  8. Kusurkar, R. S.. (1990). "Novel Synthesis of Benzosubstituted Benzofurans Via Diels-Alder Reaction". Synthetic Communications.
  9. (2005). "Heterocycles by PtCl2-Catalyzed Intramolecular Carboalkoxylation or Carboamination of Alkynes". Journal of the American Chemical Society.
Wikipedia Source

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benzofurans iarc-group-2b-carcinogens simple-aromatic-rings
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