82418-08-4Relevant academic research and scientific papers
Synthesis of N-Fused Polycyclic Indoles via Ligand-Free Palladium-Catalyzed Annulation/Acyl Migration Reaction
Dong, Zhan,Zhang, Xiao-Wen,Li, Weishuang,Li, Zi-Meng,Wang, Wen-Yan,Zhang, Yan,Liu, Wei,Liu, Wen-Bo
, p. 1082 - 1086 (2019/02/14)
An efficient synthesis of N-fused polycyclic indoles by a palladium-catalyzed annulation/acyl migration cascade reaction is described. The reaction is ligand-free, scalable, and provides access to a diverse range of useful indole scaffolds from readily available starting materials. Supporting mechanistic studies indicate that the reaction likely proceeds via an intramolecular α-arylation mechanism. The synthetic utility of this protocol is demonstrated by a gram-scale reaction and syntheses toward indole alkaloids and a HSP90 inhibitor.
Cu-Catalyzed Arylation/Acyl Migration Cascade Reaction of Enaminones: Access to N-Fused Polycyclic and 2,3-Disubstituted Indoles
Li, Weishuang,Dong, Zhan,Zhang, Yan,Zeng, Zhen,Usman, Muhammad,Liu, Wen-Bo
, p. 7995 - 8005 (2019/06/24)
An efficient synthesis of N-fused polycyclic and 2,3-disubstituted indoles by copper-catalyzed direct annulation/acyl migration reaction of enaminones is reported. This strategy features cheap and low loading of the catalyst/ligand, readily available starting materials, and good functional group compatibilities. Notably, allyl-containing substrates are also tolerated, which allows the downstream derivatization toward indole alkaloids.
Rhodium(III)-catalyzed intramolecular redox-neutral annulation of tethered alkynes: Formal total synthesis of (±)-goniomitine
Zhou, Bing,Du, Juanjuan,Yang, Yaxi,Li, Yuanchao
, p. 12768 - 12772 (2015/03/30)
A RhIII-catalyzed intramolecular redox-neutral atom-economic annulation of a tethered alkyne has been developed to efficiently construct 2-amidealkyl indoles with completely reversed regioselectivity by a C-H activation pathway. Furthermore, us
Dirhodium(II) carboxylate catalyzed formation of 1,2,3-trisubstituted indoles from styryl azides
Jones, Crystalann,Nguyen, Quyen,Driver, Tom G.
, p. 785 - 788 (2014/01/23)
Dirhodium(II)-carboxylate complexes were discovered to promote the selective migration of acyl groups in trisubstituted styryl azides to form 1,2,3-trisubstituted indoles. The styryl azides are readily available in three steps from cyclobutanone and 2-iod
Titanium-Induced Syntheses of Furans, Benzofurans and Indoles
Fuerstner, Alois,Jumbam, Denis N.
, p. 5991 - 6010 (2007/10/02)
Highly reactive titanium on graphite as the reagent of choice promotes intramolecular McMurry type reactions of acyloxy- and acylamido carbonyl compounds affording furans, benzofurans and indoles in good to excellent yields.A variety of reducible groups in the substrates is tolerated (e.g. -F, -Cl, -Br, -I, -CF3, -OMe, -CN, -thiophenyl, -COOR, -CONR2) and strained products such as 11h can be obtained, the X-ray analysis of which is reported.The experimental results indicate the possible formation of dianions from the aromatic aldehydes or ketones as reactive intermediates which attack the ester or amide functions in their proximity, rather than a radical path via ketyls.
