14182-35-5Relevant academic research and scientific papers
Palladium-catalyzed direct denitrogenative C-3-arylation of 1H-indoles with arylhydrazines using air as the oxidant
Chen, Yongxin,Guo, Shuaibo,Li, Kangning,Qu, Jinpeng,Yuan, Hua,Hua, Qiuru,Chen, Baohua
supporting information, p. 711 - 715 (2013/03/29)
A novel palladium-catalyzed approach to direct C-3-arylation of 1H-indoles with arylhydrazines using air as the oxidant via C-N bond cleavage has been developed. Various substituents are tolerated in this system in moderate to good yields. This reaction could also be compatible with a larger scale. Thus, this strategy using arylhydrazines as arylating reagents provides a powerful method for constructing substituted 3-aryl-1H-indoles. Copyright
Enamine rearrangement of pyridinium salts to indole ring: A combined experimental and molecular modeling study
Hosaan, Aisha,Fadda, Ahmed A.
, p. 638 - 644 (2013/07/19)
N-Alkyl pyridinium (II) and N-alkyl isoquinolinium salts V undergo cyclization reaction when heated with sodium bicarbonate to give the corresponding indolizine derivatives III and VI, respectively, which undergo ring opening and recyclization reactions when heated with aqueous sodium hydroxide to give the corresponding indole derivatives IV and IX, respectively. Molecular modeling tools including Molecular Mechanics using Augmented MM3 parameters followed by geometry optimization calculations in MO-G using PM3 parameters were performed to gain better understanding and more insights on the thermodynamic properties of the recyclization reactions of compounds IIa-g to the corresponding IIIa-g and IIIa-g to the corresponding IVa-g. The results were in excellent agreement with the experimental data and hence were proven to be a good tool in explaining different yields % because of the steric and electronic effects of electron-withdrawing groups on the reactivity of the pyridine ring for nucleophilic attack.
First heterogeneous ligand- and salt-free larock indole Synthesis
Batail, Nelly,Bendjeriou, Anissa,Lomberget, Thierry,Barrett, Roland,Dufaud, Veronique,Djakovitch, Laurent
supporting information; experimental part, p. 2055 - 2062 (2009/12/26)
A new ligand- and salt-free procedure using heterogeneous palladium catalysts for the Larock indole and benzofuran synthesis is reported. After optimisation of the reaction conditions, good to high isolated yields have been achieved for a variety of structures. Recycling studies have shown that the palladium catalysts can be readily recovered and reused. Reactions and recovery of the palladium catalysts can be carried out in the presence of air, without any particular precaution.
COMPOSITIONS CONTAINING, METHODS INVOLVING, AND USES OF NON-NATURAL AMINO ACIDS AND POLYPEPTIDES
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Page/Page column 147, (2008/12/06)
Disclosed herein are non-natural amino acids and polypeptides that include at least one non-natural amino acid, and methods for making such non-natural amino acids and polypeptides. The non-natural amino acids, by themselves or as a part of a polypeptide,
Cu(II)-catalyzed direct and site-selective arylation of indoles under mild conditions
Phipps, Robert J.,Grimster, Neil P.,Gaunt, Matthew J.
supporting information; experimental part, p. 8172 - 8174 (2009/02/02)
We have developed a new site-selective Cu(II)-catalyzed C-H bond functionalization process that can selectively arylate indoles at either the C3 or C2 position under mild conditions. The scope of the arylation process is broad and tolerates broad functionality on both the indole and aryl unit, which makes it amenable to further elaboration. The mechanism of the arylation reaction is proposed to proceed via a Cu(III)-aryl species that undergoes initial electrophilic addition at the C3 position of the indole motif. We speculate that site of indole arylation arises through a migration of the Cu(III)-aryl group from C3 to C2, and this can be controlled by the nature of the group on the nitrogen atom; free (NH)- and N-alkylindoles deliver the C3-arylated product, whereas N-acetylindoles afford the C2 isomer, both with excellent yield and selectivity. Copyright
METHODS FOR TREATING HEPATITIS C
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Page/Page column 415, (2010/10/20)
In accordance with the present invention, compounds that inhibit viral replication, preferably Hepatitis C Virus (HCV) replication, have been identified, and methods for their use provided. In one aspect of the invention, compounds useful in the treatment
Effect of solvent polarity on N-H insertion versus rearrangement of alkylidene carbenes
Taber, Douglass F.,Plepys, Raymond A.
, p. 6045 - 6047 (2007/10/03)
Alkylidene carbenes, when generated from o-aminobenzophenones and lithiated trimethylsilyldiazomethane, give a mixture of alkyne (by rearrangement) and indole (by N-H insertion). It has been found that this ratio of indole to acetylene shows a linear dependence on the polarity of the ethereal solvent.
