1248340-79-5Relevant articles and documents
Palladium-catalyzed intermolecular coupling of 2-haloallylic acetates with simple phenols, and sequential formation of benzofuran derivatives through the intramolecular cyclization
Udagawa, Takumi,Tsuchi, Yukiko,Takehara, Ikuma,Kogawa, Masaki,Watanabe, Hirotaka,Yamamoto, Mitsuaki,Tsuji, Hiroaki,Kawatsura, Motoi
, p. 6573 - 6579 (2017)
We accomplished the synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed reaction of 2-haloallylic acetates with simple phenols in the presence of a base. The reaction proceeded through the intermolecular attack of the nucleophile on the central carbon atom of the π-allyl group, carbon-halogen bond cleavage, and sequential intramolecular cyclization.
Synthesis of 2-substituted benzofuran derivatives by the palladium-catalyzed intermolecular coupling of 2-fluoroallylic acetates with phenols
Udagawa, Takumi,Kogawa, Masaki,Tsuchi, Yukiko,Watanabe, Hirotaka,Yamamoto, Mitsuaki,Kawatsura, Motoi
, p. 227 - 230 (2017)
We investigated the intermolecular coupling reaction of 2-fluoroallylic acetates with simple phenols by the [Pd(C3H5)Cl]2, DPPF, and KHMDS at 100?°C for 16?h, and succeeded in obtaining 2-substituted benzofuran derivatives
Oxidative Kinetic Resolution of Cyclic Benzylic Ethers
Liu, Lei,Liu, Ziqiang,Ma, Yingang,Sun, Shutao
, p. 176 - 180 (2020/10/30)
A manganese-catalyzed oxidative kinetic resolution of cyclic benzylic ethers through asymmetric C(sp3)?H oxidation is reported. The practical approach is applicable to a wide range of 1,3-dihydroisobenzofurans bearing diverse functional groups and substituent patterns at the α position with extremely efficient enantiodiscrimination. The generality of the strategy was further demonstrated by efficient oxidative kinetic resolution of another type of five-membered cyclic benzylic ether, 2,3-dihydrobenzofurans, and six-membered 6H-benzo[c]chromenes. Direct late-stage oxidative kinetic resolution of bioactive molecules that are otherwise difficult to access was further explored.
Synthesis of Functionalized Benzo[b]furans via Oxidative Cyclization of o-Cinnamyl Phenols
Rehan, Mohammad,Nallagonda, Rajender,Das, Braja Gopal,Meena, Tannu,Ghorai, Prasanta
, p. 3411 - 3424 (2017/04/13)
Disclosed herein is an efficient synthetic route for the synthesis of functionalized 2-benzyl benzo[b]furans via a regioselective 5-exo-trig intramolecular oxidative cyclization of ortho-cinnamyl phenols using [PdCl2(CH3CN)2] as catalyst and benzoquinone as an oxidant. Further, a sequential ortho-cinnamylation of phenols using cinnamyl alcohols catalyzed by Re2O7, followed by an oxidative cyclization using the above Pd catalyst, is performed. The reaction showed broad substrate scope with good to excellent yields.
Pd-Catalyzed Isocyanide Assisted Reductive Cyclization of 1-(2-Hydroxyphenyl)-propargyl Alcohols for 2-Alkyl/Benzyl Benzofurans and Their Useful Oxidative Derivatization
Rajesh, Manda,Thirupathi, Nuligonda,Jagadeshwar Reddy, Thota,Kanojiya, Sanjeev,Sridhar Reddy, Maddi
, p. 12311 - 12320 (2016/01/09)
An unusual Pd-catalyzed isocyanide assisted 5-exo-dig reductive cyclization of 1-(2-hydroxyphenyl)-propargyl alcohols is achieved for 2-alkyl/benzyl benzofurans. The reaction features a high substrate scope, insensitivity to air, and excellent product yielding. Further, a direct metal-free C-H functionalization (azidation, alkoxylation, and hydroxylation) and selective oxidative cleavage of thus synthesized 2-benzylfurans are described for azido-, alkoxy-, hydroxyl-, amide-, and tetrazolyl adducts.
Benzofuran derivatives as a novel class of inhibitors of mTOR signaling
Salomé, Christophe,Narbonne, Vanessa,Ribeiro, Nigel,Thuaud, Frédéric,Serova, Maria,De Gramont, Armand,Faivre, Sandrine,Raymond, Eric,Désaubry, Laurent
, p. 41 - 49 (2014/02/14)
High-throughput screening (HTS) hit 1 was previously identified as an inhibitor of the Akt/mTOR (Akt/mammalian target of rapamycin) signaling, which is a major target in oncology. The cytotoxicity of 1 was determined on a panel of human cancer cells lines
Controlled synthesis of 2-and 3-substituted benzo[ b ]furans
Pei, Tao,Chen, Cheng-Yi,Dimichele, Lisa,Davies, Ian W.
supporting information; experimental part, p. 4972 - 4975 (2010/12/25)
A controlled regioselective synthesis of either C-2 or C-3 substituted benzo[b]furans from readily accessible 1-(2-hydroxyphenyl)-2-chloroethanones is described. Addition of a range of Grignard reagents to the α-chloro ketones generates alkoxide intermediates, which can form either 2-substituted benzo[b]furans via a [1,2]-aryl migration or 3-substituted benzo[b]furans via a direct cyclization and dehydration sequence. A temperature-dependent [1,2]-aryl migration mechanism for the formation of 2-substituted benzo[b]furan is proposed.
