487015-93-0Relevant academic research and scientific papers
Palladium-Catalyzed Three-Component Regioselective Dehydrogenative Coupling of Indoles, 2-Methylbut-2-ene, and Carboxylic Acids
Guo, Rui-Li,Jia, Qiong,Wang, Meng-Yue,Wang, Yong-Qiang,Yang, Jin-Hui,Zhang, Xing-Long,Zhao, Bao-Yin
supporting information, p. 9574 - 9579 (2021/12/14)
Five-carbon (C5) structural units are the fundamental building blocks of many natural products. An unprecedented palladium-catalyzed three-component dehydrogenative cascade coupling of indoles, 2-methylbut-2-ene, and carboxylic acids has been developed. The approach enables the straightforward introduction of a C3′-bonded five-carbon structural unit with a tertiary alcohol quaternary carbon center into indoles. The protocol employs 2-methylbut-2-ene as the C5 source and is featured by a broad substrate scope, atom and step economies, and high chemo- and regioselectivies.
Transition-Metal-Free Ring-Opening Silylation of Indoles and Benzofurans with (Diphenyl-tert-butylsilyl)lithium
Xu, Pan,Würthwein, Ernst-Ulrich,Daniliuc, Constantin G.,Studer, Armido
supporting information, p. 13872 - 13875 (2017/10/09)
A practical method is presented for ring opening various indoles and benzofurans with concomitant stereoselective silylation using readily generated (diphenyl-tert-butylsilyl)lithium to afford ortho-β-silylvinylanilines or -phenols. Dearomatization of the heteroarene core proceeds in the absence of any transition-metal catalyst through addition of a silyl anion and a subsequent stereoselective β-elimination. DFT calculations provide insight into the mechanism. Functionalizing C?X bond cleavage of heteroarenes is rare and generally requires transition-metal catalysts.
N-(1-Oxy-2-picolyl)oxalamic acids as a new type of O,O-ligands for the Cu-catalyzed N-arylation of azoles with aryl halides in water or organic solvent
Wang, Yongbin,Zhang, Yu,Yang, Beibei,Zhang, Ao,Yao, Qizheng
, p. 4101 - 4114 (2015/03/30)
N-(1-Oxy-pyridin-2-ylmethyl)oxalamic acids (L3-L5) were identified as novel efficient ligands for copper-catalyzed C-N cross-coupling of azoles and aryl halides in water. The N-arylation of imidazoles, indoles and pyrazoles proceeded with moderate to excellent yields and complete selectivity over aromatic amines and phenols. Moreover, L5, which is also efficient in organic solvent with low catalyst loading, can be used to promote the N-arylation reactions with water-sensitive materials. The catalytic mechanism was proposed based on the results of several verification experiments which indicated that the ligands as new-type chelators may coordinate to Cu(i) with two oxygen atoms of N-oxide and amide in the coupling process. This journal is
Convenient syntheses of halo-dibenz[b,f]azepines and carbamazepine analogues via N-arylindoles
Elliott, Emma-Claire,Maggs, James L.,Park, B. Kevin,O'Neill, Paul M.,Stachulski, Andrew V.
, p. 8426 - 8434 (2013/12/04)
The dibenz[b,f]azepine heterocyclic system and related molecules with a single 10,11-bond are important templates for well-prescribed drug molecules, notably carbamazepine (anticonvulsant), clomipramine and imipramine (antidepressants). We synthesised a range of halogenated carbamazepine analogues, in connection with metabolic and immunological studies, as probes for structure-metabolism and hypersensitive effects and have published on their metabolic behaviour. While a number of synthetic routes to such analogues are possible, we naturally sought short and efficient methods for our target compounds. In the following report we present an effective two-step synthesis of a range of dibenz[b,f]azepines from appropriate indoles via N-arylation, then acid-catalysed rearrangement, with a critical analysis of other approaches. We showed earlier that this route was effective for fluoro analogues and here present a broader review of its scope. The 5-(carboxamido) side chain of carbamazepine may be added in various ways, affording overall a convenient access to drug molecules.
Convenient syntheses of benzo-fluorinated dibenz[b,f]azepines: Rearrangements of isatins, acridines, and indoles
Elliott, Emma-Claire,Bowkett, Elizabeth R.,Maggs, James L.,Bacsa, John,Park, B. Kevin,Regan, Sophie L.,O'Neill, Paul M.,Stachulski, Andrew V.
supporting information; experimental part, p. 5592 - 5595 (2011/12/03)
Efficient procedures for the synthesis of benzo-fluorinated dibenz[b,f]azepines (iminostilbenes) from fluorinated isatins or indoles using a number of ring-expansion reactions are described. A range of mono- and difluorinated analogues is accessible, and the syntheses can deliver gram quantities of the final products, which are precursors of fluoro analogues of the important anticonvulsant carbamazepine.
