57800-41-6Relevant academic research and scientific papers
Development of a one-pot sequential Sonogashira coupling for the synthesis of benzofurans
Csékei, Márton,Novák, Zoltán,Kotschy, András
, p. 8992 - 8996 (2008/12/21)
An efficient one-pot protocol was developed for the construction of the benzofuran system from aryl halides and protected iodophenols using carbinol-based acetylene sources. The sequence includes alternating palladium-catalyzed Sonogashira couplings and deprotection steps concluded by a ring closure. The developed one-pot procedure was compared with the stepwise approach and its efficiency was also demonstrated by the total synthesis of vignafuran, a benzofuran natural product.
A short-step convenient synthesis of 2-phenylbenzofuran from 3-phenylcoumarin
Kinoshita, Takeshi,Ichinose, Koji
, p. 1641 - 1654 (2007/10/03)
The reaction mechanism of chemical conversion of (E)-β-[2-hydroxylphenylethylene]benzeneethanol into 2-phenylbenzofuran by DDQ, which involves loss of one carbon unit, was characterized and described. Five naturally occurring 2-phenylbenzofurans of not only the isoflavonoid but also stilbenoid origin were synthesized by use of this chemical scheme, which proved that this new scheme is a useful tool for quick synthesis of 2-phenylbenzofurans.
Total syntheses of three natural products, vignafuran, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester, and coumestrol from a common starting material
Hiroya, Kou,Suzuki, Naoyuki,Yasuhara, Akito,Egawa, Yuya,Kasano, Atsushi,Sakamoto, Takao
, p. 4339 - 4346 (2007/10/03)
Vignafuran 2, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester 3, and coumestrol 4 were efficiently synthesized from the same starting material, 4-bromoresorcinol 14a, through the common intermediate, diarylacetylene 7. The key steps of these syntheses were the tetrabutylammonium fluoride (TBAF)-catalyzed benzo[b]furan ring formation for 2 and the carbonylative ring closure methodology catalyzed by a Pd complex for 3 and 4. The Royal Society of Chemistry 2000.
A plausible chemical analogy for biosynthesis of 2-arylbenzofuran of isoflavonoid origin and its application to synthesis of vignafuran
Kinoshita, Takeshi
, p. 259 - 262 (2007/10/03)
Treatment of 2-hydroxy-isoflav-3-ene with acid afforded 2-arylbenzofuran in good yield, and a mechanism for this chemical conversion involving loss of one carbon unit was described. This reaction scheme was suggested as a plausible chemical analogy for th
Synthesis of 2-arylbenzofuran phytoalexins
Meyer, M.,Deschamps, C.,Molho, D.
, p. 91 - 99 (2007/10/02)
A new synthesis of 2-arylbenzofuran using direct oxidative rearrangement of 2-benzyloxychalcones by Tl(ONO2)3 followed by cyclization of the key intermediates: 2-benzyloxypropan-1-ones is described.The method has been applied to the synthesis of six 2-ary
