158979-23-8Relevant academic research and scientific papers
Transition-Metal-Free Synthesis of 1,2-Disubstituted Indoles
Chesnokov, Gleb A.,Ageshina, Alexandra A.,Topchiy, Maxim A.,Nechaev, Mikhail S.,Asachenko, Andrey F.
supporting information, p. 4844 - 4854 (2019/08/01)
Herein, we report a new transition-metal-free robust and cost-effective method for synthesis of 1,2-disubstituted indoles from easily available unactivated (i.e. without EWG, PPh3 or SiR3 groups) tertiary amides. Scope of synthetic applicability of the presented protocol was shown on 23 examples of 1,2-disubstituted indoles with different substitution patterns obtained in good to excellent yields. The reported method turned out to be especially effective for synthesis of N-arylated 2-CF3-indoles. Moreover, this approach can be performed in a one-pot two-step manner directly from commercially available secondary amines. Mechanistic studies showed that acyl transfer might be an important step in the course of the reaction. Viability of the presented approach for benzofurans and benzothiophenes synthesis was also discussed.
SBA-15 Immobilized Phenanthroline-Copper(I) Complex as a Recyclable Efficient Catalyst for N-Arylation of Amides and N-H Heterocycles with Aryl Halides
Hosseinzadeh, Rahman,Aghili, Nora,Tajbakhsh, Mahmood
, p. 193 - 203 (2016/03/12)
5-(N,N-bis-3-(triethoxysilyl) propyl) ureyl-1,10-phenanthroline was prepared and successively grafted onto mesoporous silica of SBA-15 to get SBA-15 anchored ligand which was then reacted with Cu(I) to get SBA-15 anchored complex as the heterogeneous copper catalyst. This catalyst was characterized by FT-IR, XRD, CHN, AAS, TGA, EDAX, BET, SEM and TEM. The activities of the catalyst were tested in C-N cross-coupling of amides and N-H heterocycle compounds with aryl halides. The catalyst showed high catalytic activities for these cross-coupling reactions providing good to excellent yields of desired products. Moreover, the catalyst can be easily recovered by simple filtration and reused several times without significant loss of its catalytic activity.
A facile N-arylation of acetanilides with arynes
Haber, James C.,Lynch, Michael A.,Spring, Stacey L.,Pechulis, Anthony D.,Raker, Joseph,Wang, Yi
experimental part, p. 5847 - 5850 (2011/12/03)
An efficient, mild and transition-metal-free method for the N-arylation of acetanilides, leading to a range of unsymmetrical diarylamine products is reported. Reactions of ortho-silylaryl triflates with acetanilides in the presence of tetrabutylammonium triphenyldifluorosilicate (TBAT) in toluene afforded the desired products in good to excellent yields. Regioselectivity was also observed when unsymmetrical aryne precursors were used.
Copper-catalyzed amidation of aryl iodides in the presence of various chelating ligands
Hosseinzadeh, Rahman,Golchoubian, Hamid,Masoudi, Mahtab
experimental part, p. 649 - 653 (2009/05/11)
N,N′-Dibenzylethylenediamine is presented as a new, efficient, and versatile bidentate ligand suitable for the copper catalyzed formation of the C-N bond. This bidentate ligand has been demonstrated to facilitate the copper catalyzed cross-coupling reactions of aryl iodides with amides to afford the desired products in good to excellent yields.
Aryl halide tolerated electrophilic amination of arylboronic acids with N-chloroamides catalyzed by CuCl at room temperature
He, Chuan,Chen, Chong,Cheng, Jin,Liu, Chao,Liu, Wei,Li, Qiang,Lei, Aiwen
supporting information; experimental part, p. 6414 - 6417 (2009/03/11)
(Chemical Equation Presented) N-Cl is no competition: Aryl halides were tolerated in an efficient ligandless CuCl-catalyzed electrophilic amination reaction of arylboronic acids with N-chloroamides (see scheme; Ac=acetoxy). This coupling proceeded smoothly at ambient temperature, and products were obtained with good to excellent yields.
Copper-catalyzed amidation of aryl iodides using KF/Al2o 3: An improved protocol
Hosseinzadeh, Rahman,Tajbakhsh, Mahmood,Mohadjerani, Maryam,Mehdinejad, Hamidreza
, p. 1517 - 1520 (2007/10/03)
A mild method for the copper-catalyzed amidation of aryl iodides is reported. This simple C-N bond forming procedure shows that the combination of air stable CuI and 1,10-phenanthroline in the presence of KF/Al 2O3 comprises an extremely efficient and general catalyst system for the N-amidation of aryl iodides. Different functionalized aryl iodides were efficiently coupled with amides using this method.
3-piperidyl-4-oxoquinazoline derivatives and pharmaceutical compositions comprising the same
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, (2008/06/13)
3-piperidyl-4-oxoquinazoline derivatives are provided, which is represented by the formula (I): wherein R represents an amino group or a cyclic amino group such as dibenzoazepine, each of which is substituted with a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or the like, n is an integer of 1 to 3, R3and R4independently represents a hydrogen atom, a lower alkyl group, or the like, or a pharmaceutically acceptable salt thereof. Compounds (I) of the present invention have excellent MTP-inhibitory activity. Thus, these compounds not only inhibit formation of LDL that is a cause of arteriosclerotic diseases but also regulate TG, cholesterol, and lipoproteins such as LDL in the blood and regulate cellular lipids through regulation of MTP activity. They can also be used as a new type of preventive or therapeutic agents for hyperlipemia or arteriosclerotic diseases. Furthermore, they can be used as therapeutic or preventive agents for pancreatitis, obesity, hypercholesterolemia, and hypertriglyceridemia.
Sterically Hindered N-Aryl-2(1H)-Quinolones and N-Aryl-6(5H)-Phenanthridinones: Separation of Enantiomers and Barriers to Racemization
Mintas, Mhaden,Mihaljevic, Vesna,Koller, Helmut,Schuster, Doris,Mannschreck, Albrecht
, p. 619 - 624 (2007/10/02)
The novel N-aryl-4-chloro-3-methyl-2(1H)-quinolones (1)-(4) have been synthesized by condensation of the appropriate diphenylamine with diethyl methylmalonate and subsequent chlorination of the resulting N-aryl-4-hydroxy-3-methyl-2(1H)-quinolones (7)-(10). 5-(1-Naphthyl)-6(5H)-phenanthridinone (5) has been synthesized by the Chapman rearrangement of the 6-(1-naphthoxy)phenanthridine (11).Separation of the enantiomers (M) and (P) of the quinolones (1)-(4) and phenanthridinones (5), (6) was achieved by liquid chromatography on triacetylcellulose.The barriers to partial rotation about the C-N bond in (1)-(6) were determined by thermal racemization of enantiomers and are compared with those of structurally related molecules.
