26870-33-7Relevant academic research and scientific papers
Convenient Access to meta-Substituted Phenols by Palladium-Catalyzed Suzuki–Miyaura Cross-Coupling and Oxidation
Wang, Zi,Orellana, Arturo
, p. 11445 - 11449 (2017/08/26)
We report a new approach to the synthesis of meta-substituted phenols in which a single palladium catalyst accomplishes a Suzuki–Miyaura cross-coupling between a β-chlorocyclohexenone and an arylboronic acid, and oxidation of the resulting cyclohexenone to the corresponding phenol upon introduction of a terminal oxidant and electron transfer mediator. Notably, this method also allows ready access to ortho, meta-disubstituted phenols, sterically congested biaryl phenols, and more highly substituted phenols.
An efficient approach to construct 2-arylbenzo[b]furans from 2-methoxychalcone epoxides
Ruan, Libo,Shi, Min,Mao, Shiwei,Yu, Lifang,Yang, Fan,Tang, Jie
, p. 1065 - 1070 (2014/01/23)
An efficient and practical method for construction of 2-arylbenzo[b]furans from 2-methoxychalcone epoxides has been reported. Catalyzed by 2 mol % of BF3·Et2O, 2-methoxychalcone epoxides went through the Meerwein rearrangement, followed by deformylation in one-pot to successfully afforded 2-methoxydeoxybenzoins. Afterward, 2-arylbenzo[b]furans were obtained in high yields (87%-100%) via intermolecular cyclodehydration of 2-methoxydeoxybenzoins with 48% HBr. By utilization of this approach, the natural product stemofuran A and the key intermediate of eupomatenoid 6 have been synthesized conveniently.
Multi-target strategy to address Alzheimer's disease: Design, synthesis and biological evaluation of new tacrine-based dimers
Rizzo, Stefano,Bisi, Alessandra,Bartolini, Manuela,Mancini, Francesca,Belluti, Federica,Gobbi, Silvia,Andrisano, Vincenza,Rampa, Angela
, p. 4336 - 4343 (2011/11/07)
The multifactorial nature of Alzheimer's disease (AD) offers us a textbook example where parental compounds, mostly marketed, are modified with the aim of improving and/or conferring two or even more biological activities to contrast or less frequently re
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.
Highly effective synthetic methods for substituted 2-arylbenzofurans using [3,3]-sigmatropic rearrangement: Short syntheses of stemofuran A and eupomatenoid 6
Miyata, Okiko,Takeda, Norihiko,Naito, Takeaki
, p. 1761 - 1763 (2007/10/03)
Matrix presented. A new and efficient synthesis of 2-arylbenzofurans has been achieved via a route involving acylation and subsequent [3,3]-sigmatropic rearrangement of oxime ethers. Its synthetic utility is demonstrated by a short synthesis of stemofuran
Syntheses of 3-arylphenols from (3-aryl-3-oxopropyl)dialkylammonium chlorides and 1-(2-Oxopropyl)pyridinium chloride
Eichinger,Nussbaumer
, p. 663 - 664 (2007/10/02)
The reactions of (3-aryl-3-oxopropyl)dialkylammonium chlorides 1a-f with 1-(2-oxopropyl)pyridinium chloride (2) and triethylamine gave the 3-arylphenols 3a-f with yields from 43 to 83%.
