179253-65-7Relevant academic research and scientific papers
Synthesis of (Thio)Furan-Fused Phospholes via Phosphonation Cyclization and a Base-Promoted Phospha-Friedel-Crafts Reaction
Chen, Siyu,Ding, Haixin,Hua, Yuhui,Huang, Haiyang,Li, Chenchen,Liu, Fen,Song, Xian-Rong,Xiao, Qiang,Yuan, Chengxiong
supporting information, (2022/02/07)
Herein, we developed a novel strategy for synthesizing ladder (thio)furan-fused phospholes via intermolecular phosphonation cyclization and a base-promoted phospha-Friedel-Crafts reaction under mild conditions. The starting substrates are readily available phosphinic acids and easy-to-handle alkynes. The details of the reaction mechanism were further rationalized using theoretical calculations. This protocol can be widely applied to synthesize furan- and thiofuran-fused phospholes as well as the corresponding large π-extended derivatives, which are of great interest in the domain of organic functional materials.
Template-Hopping Approach Leads to Potent, Selective, and Highly Soluble Bromo and Extraterminal Domain (BET) Second Bromodomain (BD2) Inhibitors
Aylott, Helen E.,Atkinson, Stephen J.,Bamborough, Paul,Bassil, Anna,Chung, Chun-Wa,Gordon, Laurie,Grandi, Paola,Gray, James R. J.,Harrison, Lee A.,Hayhow, Thomas G.,Messenger, Cassie,Mitchell, Darren,Phillipou, Alexander,Preston, Alex,Prinjha, Rab K.,Rianjongdee, Francesco,Rioja, Inmaculada,Seal, Jonathan T.,Wall, Ian D.,Watson, Robert J.,Woolven, James M.,Demont, Emmanuel H.
, p. 3249 - 3281 (2021/04/06)
A number of reports have recently been published describing the discovery and optimization of bromo and extraterminal inhibitors which are selective for the second bromodomain (BD2); these include our own work toward GSK046 (3) and GSK620 (5). This paper describes our approach to mitigating the genotoxicity risk of GSK046 by replacement of the acetamide functionality with a heterocyclic ring. This was followed by a template-hopping and hybridization approach, guided by structure-based drug design, to incorporate learnings from other BD2-selective series, optimize the vector for the amide region, and explore the ZA cleft, leading to the identification of potent, selective, and bioavailable compounds 28 (GSK452), 39 (GSK737), and 36 (GSK217).
Synthesis of diarylalkanes through an intramolecular/intermolecular addition sequence by auto-tandem catalysis with strong Br?nsted base
Kondoh, Azusa,Ma, Chaoyan,Terada, Masahiro
, p. 10894 - 10897 (2020/10/02)
An auto-tandem catalysis with a strong Br?nsted base enabled the synthesis of diarylalkanes containing a benzofuran moiety. Potassiumtert-butoxide efficiently catalyzed both the intramolecular cyclization of less acidicortho-alkynylaryl benzyl ethers and the following intermolecular addition of diarylmethanes to styrenes, demonstrating the high potential of the catalysis in organic synthesis.
Visible light-induced radical addition/annulation to construct phenylsulfonyl-functionalized dihydrobenzofurans involving an intramolecular 1,5-hydrogen atom transfer process
Sun, Peipei,Xie, Shentong,Li, Yifan
, p. 8774 - 8779 (2020/12/02)
A visible light-induced radical cascade reaction of 2-alkynylarylethers with sodium sulfinates was established for the synthesis of sulfonyl-functionalized dihydrobenzofurans, and an intramolecular 1,5-hydrogen atom transfer was involved in this transformation. This process provided an efficient and convenient C-C formation protocol for the construction of a dihydrobenzofuran ring. Various substituents on 2-alkynylarylethers and sodium sulfinates were tolerated in the reaction, and the corresponding products were obtained in moderate to good yields.
From ynamides to highly substituted benzo[b]furans: Gold(I)-catalyzed 5-endo-dig-cyclization/rearrangement of alkylic oxonium intermediates
Blanco Jaimes, Maria Camila,Weingand, Vanessa,Rominger, Frank,Hashmi, A. Stephen K.
, p. 12504 - 12511 (2013/09/23)
A series of arylynamides with alkyloxy groups at the ortho position of the aryl group was prepared through a short alkylation/cross-coupling/amidation sequence. The gold-catalyzed conversion of these substrates combined both C-O and C-C formation steps, thus providing benzofurans with amine functionalities at the 2-position and alkyl groups at the 3-position. Cross-over experiments showed that the alkyl-migration step was an intermolecular process. X-ray crystal-structure analysis of two of the products supported our structural assignment. In some cases, the corresponding benzofurans without the alkyl group at the 3-position were obtained as side-products, which were formed through a competing protodeauration process. Golden touch: Arylynamides with o-alkyloxy groups were prepared through an alkylation/cross-coupling/amidation sequence. Their Au-catalyzed conversion provided benzofurans with amine groups at the 2-position and alkyl groups at the 3-position. Copyright
Enantioselective catalysis 107: new optically active deltacyclenes as building blocks for the synthesis of expanded phosphanes
Brunner, Henri,Reimer, Alfred
, p. 307 - 314 (2007/10/03)
The cobalt-catalyzed homo Diels-Alder reaction of norbornadiene and terminal acetylenes yields chiral deltacyclenes.We tried to extend the scope of this reaction to acetylenes containing a heteroatom (i) in the propargylic position, (ii) in the ortho position of phenylacetylene or (iii) directly bonded to the triple bond.The synthesis of nine new substituted deltacyclenes with cobalt cytalysts derived from CoI2 and zinc powder or Co(acac)3 and Et2AlCl is described.Using Norphos as a cocatalyst, the products are obtained in high enantiomeric excess. - Keywords: enantioselective homogeneous catalysis; homo Diels-Alder reaction; deltacyclene; terminal acetylene
