40492-53-3Relevant academic research and scientific papers
A biomimetic approach to dihydrobenzofuran synthesis
Benbow,Katoch-Rouse
, p. 4965 - 4972 (2007/10/03)
A method for an acid-catalyzed construction of dihydrobenzofuran heterocycles (14) from 2-(2′-hydroxyethyl)quinone precursors 10 is presented. The putative oxonium ion intermediate 17 formed by an intramolecular hydroxyl cyclization followed by dehydration is reduced in situ by an added dihydroquinone source. Good to excellent yields of cyclized products are realized in all cases except for highly electron deficient systems, and these suffer reduction prior to oxonium ion formation. All products are monomeric and derived from a two-electron transfer except for 10g, which affords the dimeric dihydrobenzofuran. The amount of cyclization or reduction product is governed by the HOMO/LUMO gap between the quinone substrate and the dihydroquinone additive, and the product distribution can be adjusted by modifying the electronic properties of the added reducing agent.
One-pot Claisen rearrangement/O-methylation/alkene isomerization in the synthesis of ortho-methoxylated phenylisopropylamines
Waldman, Steve R.,Monte, Aaron P.,Bracey, Ann,Nichols, David E.
, p. 7889 - 7892 (2007/10/03)
An improved synthesis of a potent serotonin agonist 1a and its novel derivative 1b is described, making use of a Claisen rearrangement whose unstable phenolic product is methylated and isomerized in situ. This method may be of general use in the synthesis of α-methoxylated phenethylamine derivatives. The synthesis also includes an unusual, one pot demethylation/primary alcohol bromination with boron tribromide.
6-substituted 5-hydroxy-2,3-dihydrobenzofurans as inhibitors of leukotriene biosynthesis
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, (2008/06/13)
Novel position-4 and/or position-6 substituted 5-hydroxy-2,3-dihydrobenzofuran and analogs of the following general structural formula (I) are disclosed: STR1 These compounds are found to be potent inhibitors of leukotriene biosynthesis.
2,3-Dihydro-5-benzofuranols as antioxidant-based inhibitors of leukotriene biosynthesis
Hammond,Kopka,Zambias,Caldwell,Boger,Baker,Bach,Luell,MacIntyre
, p. 1006 - 1020 (2007/10/02)
The enzymes that catalyze the oxidative metabolism of arachidonic acid have provided fertile ground for the development of useful therapeutic agents for nearly a quarter century. Inhibitors of the enzyme cyclooxygenase prevent the formation of the prostag
Synthesis of 6-(3-Aryl-2-propenyl)-2,3-dihydro-5-hydroxybenzofuran Derivatives by Cross Coupling Reactions
Alabaster, Ramon J.,Cottrell, Ian F.,Hands, David,Humphrey, Guy R.,Kennedy, Derek J.,et al.
, p. 598 - 603 (2007/10/02)
The synthesis of 6-(3-aryl-2-propenyl)-2,3-dihydro-5-hydroxybenzofuran derivatives by cross coupling between 6-bromo-2,3-dihydrobenzofurans and cinnamyl halides via organo-metallic compounds has been explored.Palladium catalysed reaction between benzofury
