34125-69-4Relevant academic research and scientific papers
Synthesis of Enantioenriched 3,4-Disubstituted Chromans through Lewis Base Catalyzed Carbosulfenylation
Denmark, Scott E.,Laverny, Aragorn,Menard, Travis
, p. 14290 - 14310 (2021/11/12)
A method for the catalytic, enantioselective, carbosulfenylation of alkenes to construct 3,4-disubstituted chromans is described. Alkene activation proceeds through the intermediacy of enantioenriched, configurationally stable thiiranium ions generated from catalytic, Lewis base activation of an electrophilic sulfenylating agent. The transformation affords difficult-to-generate, enantioenriched, 3,4-disubstituted chromans in moderate to high yields and excellent enantioselectivities. A variety of substituents are compatible including electronically diverse functional groups as well as several functional handles such as aryl halides, esters, anilines, and phenols. The resulting thioether moiety is amenable to a number of functional group manipulations and transformations. Notably, the pendant sulfide was successfully cleaved to furnish a free thiol which readily provides access to most sulfur-containing functional groups which are present in natural products and pharmaceuticals.
A dehydrogenative diels-alder reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone
Feng, Hong-Xia,Wang, Yuan-Yuan,Chen, Jie,Zhou, Ling
supporting information, p. 940 - 944 (2015/03/30)
An efficient dehydrogenative Diels-Alder (DHDA) reaction of prenyl derivatives with 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) has been developed under mild conditions, leading to a series of cyclohexene derivatives with good to excellent yields and excellent diastereoselectivity.
Gold-catalyzed intramolecular hydroarylation of olefins. Scope evaluation and preliminary mechanistic studies
Jean, Mickael,Van De Weghe, Pierre
supporting information; experimental part, p. 3509 - 3513 (2011/07/09)
We report a gold-catalyzed intramolecular hydroarylation of unactivated olefins using a combination of AuCl3/AgOTf as the catalytic system affording dihydrobenzopyrans, tetralins and tetrahydroquinolines in good yields. For our preliminary mechanistic studies, we have investigated the kinetic isotope effects with deuterated arene compounds and found that this catalytic hydroarylation is consistent with an electrophilic aromatic substitution process.
N,N-dimethylglycine-promoted ullmann-type coupling reactions of aryl iodides with aliphatic alcohols
Zhang, Hui,Ma, Dawei,Cao, Weiguo
, p. 243 - 246 (2007/10/03)
The Ullmann-type coupling reactions of aryl iodides and aliphatic alcohols occur at 110°C with N,N-dimethylglycine as the ligand, giving aryl alkyl ethers in good to excellent yields. Georg Thieme Verlag Stuttgart.
Reaction between phenols and isoprene under zeolite catalysis. Highly selective synthesis of chromans and o-isopentenylphenols
Bigi, Franca,Carloni, Silvia,Maggi, Raimondo,Muchetti, Chiara,Rastelli, Massimo,Sartori, Giovanni
, p. 301 - 304 (2007/10/03)
Chromans 3 and o-isopentenylphenols 4 are synthesized in satisfactory to good yields and selectivities by the reaction of phenols and isoprene in the presence of the commercially available acid faujasite zeolite HSZ-360.
Facile synthesis of 2,2-Dimethylchromans by Mo(CO)6 Catalyzed reaction of aryl prenyl ethers
Bernard, Angela M.,Cocco, Maria T.,Onnis, Valentina,Piras, Pier P.
, p. 256 - 258 (2007/10/03)
2,2-Dimethylchromans 3a-g are synthesized in good yields by a one-pot reaction of the aryl prenyl ethers 1a-g with a catalytic amount of Mo(CO)6 in refluxing toluene.
Total synthesis of polyprenylhydroquinols and benzoquinones
Bouzbouz, Samir,Kirschleger, Bernard,Villieras, Jean
, p. 67 - 84 (2007/10/03)
The total synthesis of polyprenylhydroquinols and benzoquinones is described.First, two appropriate aromatic allyl carbonates (moieties with one and two prenyls) and two activated bifunctional terpenyl derivatives (moieties with two and three prenyls) were synthesized.These molecules were then reacted together using a highly regio- and stereoselective coupling with Pd(PPh3)4 as a catalyst.The synthesis was achieved by functional group elimination and formation of quinonic and hydroquinonic moieties. - Keywords: polyprenylbenzoquinol; polyprenylhydroquinone; allylcarbonate; ?-allyl palladium complex
Total synthesis of 2-tetraprenylbenzoquinol and -benzoquinone
Bouzbouz,Kirschleger
, p. 714 - 718 (2007/10/02)
The total synthesis of 2-tetraprenylbenzoquinol and -benzoquinone is described. A key step in this synthesis is the highly regio- and stereoselective coupling between an appropriate aromatic allylcarbonate and an activated bifunctional farnesyl derivative
5-hydroxy-2,3-dihydrobenzofuran analogs as leukotriene biosynthesis inhibitors
-
, (2008/06/13)
Compounds of the formula: STR1 where R2 contains certain aryls or heteroaryls are effective leukotriene inhibitors.
Development of 2,3-Dihydro-6-(3-phenoxypropyl)-2-(2-phenylethyl)-5-benzofuranol (L-670,630) as a Potent and Orally Active Inhibitor of 5-Lipoxygenase
Lau, Cheuk K.,Belanger, Patrice C.,Dufresne, Claude,Scheigetz, John,Therien, Michael,et al.
, p. 1299 - 1318 (2007/10/02)
Leukotrienes are potent biological mediators of allergic and antiinflammatory diseases and are derived from arachidonic acid through the action of the 5-lipoxygenase.In this study, the syntheses and comparative biological activities of three series of 2,3-dihydro-2,6-disubstituted-5-benzofuranols with various substituents on position 3 are described.Compounds from each series were evaluated for their ability to inhibit the production of leukotriene B4 (LTB4) in human peripheral blood polymorphonuclear (PMN) leukocytes and the 5-lipoxygenase reaction in cell-free preparations from rat PMN leukocytes.The structure-activity relationships of each series in vitro and in vivo are presented.The bioavailability, metabolism, and toxicity profile of each series are discussed.The series with no substituent at position 3 was the most potent and among the compounds in that series 2,3-dihydro-6-(3-phenoxypropyl)2-(2-phenylethyl)-5-benzofuranol (46, L-670,630) was chosen for further development.
