37883-65-1Relevant academic research and scientific papers
Interrupting Base-Mediated Benzofuran Ring Transformation with Michael Acceptors
Srinivas, Kolluru,Sharma, Rashmi,Ramana, Chepuri V.
, p. 9816 - 9823 (2017/09/23)
A simple two-stage approach for the synthesis of 3-(2-arylbenzofuran-3-yl)propanoates and propanamides has been developed employing simple acrylates and acrylamides and readily available 3-aroylbenzofurans. The key step of this process involves a base-mediated ring opening of the 3-aroylbenzofurans and subsequent Michael addition of the resulting 1,3-dicarbonyl intermediate with acrylate/acrylamide, followed by the deformylation in one-pot. The resulting products undergo an acid-mediated dehydrative cyclization to arrive at these targets.
Design of a New Bimetallic Catalyst for Asymmetric Epoxidation and Sulfoxidation
Bhadra, Sukalyan,Akakura, Matsujiro,Yamamoto, Hisashi
supporting information, p. 15612 - 15615 (2016/01/09)
A new chiral tethered 8-quinolinol-based ligand class is developed. The binuclear titanium complex of the ligand operates through a novel mechanism allowing for the regio- and stereoselective epoxidation of primary and tertiary homoallylic alcohols (up to 98% ee), as well as first examples of 2-allylic phenols (up to 92% ee). The new catalyst system also promotes the asymmetric oxidation of γ-hydroxypropyl sulfides giving an important class of chiral sulfoxides that have been inaccessible to date (up to 95% ee).
Ring-expansion protocol: Preparation of synthetically versatile dihydrotropones
Do, Young-Sun,Sun, Ruiying,Kim, Hee Jin,Yeo, Jung Eun,Bae, Sung-Hee,Koo, Sangho
experimental part, p. 917 - 920 (2009/06/20)
A ring-expansion protocol that consisted of the 1,2-addition of various enolate nucleophiles to 6-trimethylsiloxy-2- cyclohexene-1-one (1) and the NaIO4-promoted oxidative ring opening of the resulting diols 2, followed by an intramolecular Kno
Reactions of 2-hydroxybenzophenones with Corey-Chaykovsky reagent
Chittimalla, Santhosh Kumar,Chang, Tsung-Che,Liu, Ting-Chun,Hsieh, Hsing-Pang,Liao, Chun-Chen
, p. 2586 - 2595 (2008/09/19)
A variety of 2-hydroxybenzophenones on reaction with Corey-Chaykovsky reagent underwent unprecedented rearrangements leading to 3-substituted benzofurans 8 and one-carbon homologated compounds 9 and 12. Compounds 9 could further be quantitatively transfor
One-pot synthesis of benzofurans via palladium-catalyzed enolate arylation with o-bromophenols
Eidamshaus, Christian,Burch, Jason D.
supporting information; experimental part, p. 4211 - 4214 (2009/06/06)
(Chemical Equation Presented) A one-pot synthesis of benzofurans which utilizes a palladium-catalyzed enolate arylation is described. The process demonstrates broad substrate scope and provides differentially substituted benzofurans in moderate to excelle
Novel highly regioselective VO(acac)2/TBHP mediated oxidation of o-alkenyl phenols to o-hydroxybenzyl ketones
Lattanzi, Alessandra,Senatore, Antonello,Massa, Antonio,Scettri, Arrigo
, p. 3691 - 3694 (2007/10/03)
A novel mild methodology for the preparation of o-hydroxybenzyl ketones is described starting from o-alkenyl phenols and based on the VO(acac)2/TBHP (2 mol %/1.2 equiv) system. VO(acac)2 first catalyzes the epoxidation of o-alkenyl phenols and then the rearrangement of the epoxyphenols to ketones via the selective benzylic C-O cleavage and 1,2 hydride migration. The protocol has also been applied to set up a useful and easy one-pot conversion of o-alkenyl phenols to benzo[b]furans by means of the sequential addition of TFA, after the generation of the intermediate o-hydroxybenzyl ketones.
REDUCTION PAR LES SELS CHROMEUX DE BROMURES BENZYLIQUES ORTHO-O-ACYLES AVEC TRANSPOSITION DU GROUPEMENT ACYLE DE L'ESTER: ACCES AUX ORTHO-HYDROXYBENZYL CETONES NON MASQUEES ET UNE NOUVELLE PREPARATION DE BENZO(B)FURANNES SUBSTITUES EN POSITION-2
Ledoussal, B.,Gorgues, A.,Coq, A. Le
, p. 5841 - 5852 (2007/10/02)
The ?-bonded organochromium (III) complexes resulting from the reduction of ortho-O-acyl benzylic bromides 1 with CrCl2 undergo an 1,5-transposition of the ester acyl functional group which allows, through selected experimental conditions either a selective access to the unmasked ortho-hydroxybenzyl ketones 2 or a new preparation of the 2-substituted benzofurans 3.The scope and limitations of the method are presented.
Chromium(II) Salt mediated Reductive Transposition of an Ester Acyl Group in ortho-O-Acyl Benzylic Bromides: a Ready Access to Unmasked ortho-Hydroxybenzyl Ketones and a New Route to Benzofurans
Ledoussal, Benoit,Gorgues, Alain,Coq, Andre Le
, p. 171 - 172 (2007/10/02)
The mono-ο-bonded organochromium(III) complexes (A) derived from (1) rearrange internally into (B) through an acyl ester group transposition, selected experimental conditions allowing either a good access to the unmasked ortho-hydroxybenzyl ketones (2) or a new route to the 2-substituted benzofurans (3).
Oxidative Conversions of Sulfene Cycloadducts from Azaheptafulvenes and from Tropone to 1,2-Disubstituted Indoles and 2-Arylbenzofurans, Respectively
Dean, Barry D.,Truce, William E.
, p. 3575 - 3576 (2007/10/02)
The cycloadducts from azaheptafulvenes and sulfenes as well as from tropone and arylsulfenes rearrange upon oxidation of their corresponding α-sulfonyl anions to give 1,2-disubstituted indoles and 2-arylbenzofurans.
