263887-30-5Relevant academic research and scientific papers
Cascade Synthesis of 3-Alkylidene Dihydrobenzofuran Derivatives via Rhodium(III)-Catalyzed Redox-Neutral C-H Functionalization/Cyclization
Zhou, Zhi,Liu, Guixia,Chen, Yan,Lu, Xiyan
, p. 5874 - 5877 (2015)
An efficient rhodium(III)-catalyzed coupling reaction of N-phenoxyacetamides with propargyl carbonates to yield 3-alkylidene dihydrobenzofuran derivatives via C-H functionalization/cascade cyclization has been developed. This transformation represents a r
Synthesis and cytotoxic activities of novel hybrid 2-phenyl-3- alkylbenzofuran and imidazole/triazole compounds
Chen, Wen,Deng, Xiao-Yan,Li, Yan,Yang, Li-Juan,Wan, Wei-Chao,Wang, Xue-Quan,Zhang, Hong-Bin,Yang, Xiao-Dong
, p. 4297 - 4302 (2013/07/26)
A series of novel hybrid compounds of 2-phenyl-3-alkylbenzofuran and imidazole or triazole were prepared and evaluated in vitro against a panel of human tumor cell lines. The results suggest that the 2-ethyl-imidazole ring, and substitution of the imidazo
Rhodium(III)-catalyzed redox-neutral coupling of N-phenoxyacetamides and alkynes with tunable selectivity
Liu, Guixia,Shen, Yangyang,Zhou, Zhi,Lu, Xiyan
, p. 6033 - 6037 (2013/07/19)
Give it a tweak: A novel oxidizing directing group was developed for a rhodium(III)-catalyzed C-H functionalization of N-phenoxyacetamides with alkynes. A small change in the reaction conditions leads to either ortho-hydroxyphenyl-substituted enamides or cyclization to deliver benzofurans with high selectivity (see scheme; Cp=C5Me5). Copyright
Synthesis of 2,3-disubstituted benzofurans and indoles by π-Lewis acidic transition metal-catalyzed cyclization of ortho-alkynylphenyl O,O- and N,O-acetals
Nakamura, Itaru,Mizushima, Yuya,Yamagishi, Uichiro,Yamamoto, Yoshinori
, p. 8670 - 8676 (2008/02/08)
The PtCl2-catalyzed cyclization reaction of ortho-alkynylphenyl acetals 1 in the presence of COD (1,5-cyclooctadiene) produces 3-(α-alkoxyalkyl)benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl)phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl)phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal (1f) in the presence of 2 mol % of platinum(II) chloride and 8 mol % of 1,5-cycloocatadiene in toluene at 30 °C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively. Moreover, the reaction of N-methoxymethyl-2-alkynylanilines 3 was catalyzed by PdBr2, affording the corresponding 2,3-disubstituted indoles 4 in moderate yields. For example, the reaction of N-methoxymethyl-2-(1-pentynyl)-N-tosylaniline (3a) and N-methoxymethyl-2-(phenylethynyl)-N-tosylaniline (3b) in the presence of 10 mol % of PdBr2 in toluene at 80 °C gave 3-methoxymethyl-2-propyl-1-tosylindole (4a) and 3-methoxymethyl-2-phenyl-1-tosylindole (4b) in 33 and 33% yields, respectively.
Synthesis of 2,3-disubstituted benzofurans by platinum olefin-catalyzed carboalkoxylation of o-alkynylphenyl acetals
Nakamura, Itaru,Mizushima, Yuya,Yamamoto, Yoshinori
, p. 15022 - 15023 (2007/10/03)
The PtCl2-catalyzed cyclization reaction of o-alkynylphenyl acetals 1 in the presence of 1,5-cyclooctadiene produces 3-(α-alkoxyalkyl)benzofurans 2 in good to high yields. For example, the reaction of acetaldehyde ethyl 2-(1-octynyl)phenyl acetal (1a), acetaldehyde ethyl 2-(cyclohexylethynyl)phenyl acetal (1c), and acetaldehyde ethyl 2-(phenylethynyl)phenyl acetal (1f) in the presence of 2 mol % of platinum(II) chloride and 8 mol % of 1,5-cyclooctadiene in toluene at 30 °C gave the corresponding 2,3-disubstituted benzofurans 2a, 2c, and 2f in 91, 94, and 88% yields, respectively. Copyright
An expeditious synthesis of vibsanol, a benzofuran-type lignan from Viburnum awabuki
Sakai, Atsushi,Aoyama, Toyohiko,Shioiri, Takayuki
, p. 643 - 659 (2007/10/03)
Vibsanol (1), a benzofuran-type lignan isolated from the wood of Viburnum awabuki (Caprifoliaceae), was synthesized from the readily available vanillin; the key step is a tandem cyclization of o-tert- butyldimethylsiloxydiarylalkyne (2) with tetrabutylammonium fluoride and excess paraformaldehyde.
Total synthesis of vibsanol, a benzofuran-type lignan
Sakai, Atsushi,Aoyama, Toyohiko,Shioiri, Takayuki
, p. 4211 - 4214 (2007/10/03)
Vibsanol (1), a benzofuran-type lignan isolated from the wood of Viburnum awabuki (Caprifoliaceae), was synthesized by the tandem cyclization of o-tert-butyldimethylsiloxydiarylalkyne with tetrabutylammonium fluoride and excess paraformaldehyde as the key step.
