80079-25-0Relevant articles and documents
NEW METHOD FOR THE REDUCTION OF BENZOFURANS
Borisova, L. N.,Rozenberg, S. G.,Kucherova, N. F.,Zagorevskii, V. A.
, p. 869 - 871 (1981)
A new method for the reduction of benzofurans with potassium and sodium borohydrides in CF3COOH was developed.It is shown by gas-liquid chromatography and PMR spectroscopy that mixtures (ca. 2:3) of the cis and trans isomers of dihydro derivatives of benzofuran are formed in the reduction.The mechanism of the reduction includes intermolecular transfer of a hydride ion to the protonated form of the benzofuran.
Short communication: Titanium-induced synthesis of benzofurans
Jumbam,Yedwa,Masamba
experimental part, p. 157 - 160 (2012/05/20)
Ketoesters derived from the acylation of o-hydroxyacetophenone with aliphatic as well as aromatic acid chlorides undergo intramolecular cyclization in the presence of low-valent titanium to afford benzofurans in good yields. The reduction of titanium trichloride with dry zinc powder in refluxing THF takes place in the presence of the ketoester which simultaneously cyclizes as the titanium catalyst is formed, rendering the pre-reduction of titanium trichloride in a separate step unnecessary.
Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: Short synthesis of natural 2-arylbenzofurans
Takeda, Norihiko,Miyata, Okiko,Naito, Takeaki
, p. 1491 - 1509 (2008/09/19)
A new synthetic method for the preparation of benzofurans has been developed. The key step of this method is the [3,3]-sigmatropic rearrangement of N-trifluoroacetyl-ene-hydroxylamines, which was triggered by acylation of oxime ethers. TFAA has been proved to be the best reagent to induce [3,3]-sigmatropic rearrangement for the synthesis of cyclic or acyclic dihydrobenzofurans. On the other hand, the TFAT-DMAP system is found to be the most effective for constructing various benzofurans. Synthetic utility of this reaction is demonstrated by the short synthesis of natural benzofurans without protection of the hydroxy group. The synthesis of Stemofuran A was accomplished via condensation of ketones with aryloxyamine and subsequent reaction with TFAT-DMAP in a four-step synthesis with 72% overall yield. Similarly, Eupomatenoid 6 and Coumestan were synthesized through the reaction of oxime ether with TFAT-DMAP. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.