98883-35-3Relevant 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.
Divergent Coupling of 2-Carbonyl-anilines and Diazo-cyclopentanones: Asymmetric Total Synthesis of (+)-Leucomidine A
Yao, Xiaotong,Shan, Xiaosong,Zu, Liansuo
supporting information, p. 6498 - 6501 (2018/10/15)
The direct coupling of 2-carbonyl-anilines and diazo-cyclopentanones, promoted by a rhodium catalyst and diphenyl phosphate, is reported for the divergent generation of both carbazolones and indolones. The strategy allows for the successful transfer of the substituents/functionality and the chirality of the coupling partners into the functionalized heterocyclic products, thus serving as the strategic basis for natural product synthesis as demonstrated by the concise asymmetric total synthesis of (+)-leucomidine A.
Palladium-catalyzed coupling of vinylogous amides with aryl halides: Applications to the synthesis of heterocycles
Edmondson, Scott D.,Mastracchio, Anthony,Parmee, Emma R.
, p. 1109 - 1112 (2007/10/03)
Described herein is the first example of the palladium-catalyzed coupling of vinylogous amides with aryl bromides and chlorides. The scope of this reaction with respect to the aryl component is investigated. Additionally, a tandem reaction sequence in which the above coupling is followed by an intramolecular Heck reaction is presented. These reactions can be applied to high-yielding, one-pot syntheses of nitrogen-containing heterocycles.
