117908-10-8Relevant articles and documents
Rapid Syntheses of Heteroaryl-Substituted Imidazo[1,5-a]indole and Pyrrolo[1,2-c]imidazole via Aerobic C2-H Functionalizations
Kong, Wei-Jun,Chen, Xingrong,Wang, Mingming,Dai, Hui-Xiong,Yu, Jin-Quan
, p. 284 - 287 (2018)
Here we report an aerobic Pd(0) catalyzed C2-H functionalization of indoles and pyrroles with tethered N-methoxylamide as the directing group. A Pd(0)-initiated mechanism overcomes the directing or poisoning effect from a wide range of heterocycles including pyridine, pyrimidine, and thiazole. The imidazo[1,5-a]indole products are transformed to bioactive analogs after one-step manipulations, demonstrating the potential utility of this reaction in drug discovery.
A Micellar Catalysis Strategy for Suzuki-Miyaura Cross-Couplings of 2-Pyridyl MIDA Boronates: No Copper, in Water, Very Mild Conditions
Isley, Nicholas A.,Wang, Ye,Gallou, Fabrice,Handa, Sachin,Aue, Donald H.,Lipshutz, Bruce H.
, p. 8331 - 8337 (2017/12/08)
Suzuki-Miyaura (SM) cross-couplings of 2-pyridyl MIDA boronates can be successfully carried out in the complete absence of copper by attenuation of the Lewis basicity associated with the pyridyl nitrogen using selected substituents (e.g., fluorine or chlorine) on the ring. This strategy imparts additional synthetic options compared with existing approaches based on the use of Lewis acids or N-oxides. Thus, access to highly valued 2-substituted pyridyl rings via an initial Suzuki-Miyaura coupling can be followed by dehalogenation, SNAr reactions, or a second SM coupling to arrive at 2,6-disubstituted pyridyl arrays, all run in a single pot, enabled by micellar catalysis in water. Accessing targets within drug-like space is demonstrated in a four-step, one-pot sequence. Computational data suggest that the major role being played by electron-withdrawing substituents in promoting these cross-couplings without the need for copper is to slow the rates of protodeboronation of intermediate 2-pyridylboronic acids.
Design, synthesis and biological evaluation of indole derivatives as Vif inhibitors
Pu, Chunlan,Luo, Rong-Hua,Zhang, Mengqi,Hou, Xueyan,Yan, Guoyi,Luo, Jiang,Zheng, Yong-Tang,Li, Rui
supporting information, p. 4150 - 4155 (2017/08/22)
The crystal structure of viral infectivity factor (Vif) was reported recently, which makes it possible to design new inhibitors against Vif by structure-based drug design. Through analysis of the protein surface of Vif, the C2 pocket located in the N-terminal was found, which is suit for developing small molecular inhibitors. Then, in our article, fragment-based virtual screening (FBVS) was conducted and a series of fragments was obtained, among which, Zif-1 bearing indole scaffold and pyridine ring can form H-bonds with Tyr148 and Ile155. Subsequently, 19 derivatives of Zif-1 were synthesized. Through the immune-fluorescence staining and Western blot assays, Zif-15 shows potent activity in inhibiting Vif-mediated A3G degradation. Further docking experiment shows that Zif-15 form H-bond interactions with residues His139, Tyr148 and Ile155. Therefore, Zif-15 is a promising lead compound against Vif that can be used to treat AIDS.
General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand
Zou, Yinjun,Yue, Guizhou,Xu, Jianwei,Zhou, Jianrong
supporting information, p. 5901 - 5905 (2015/03/30)
A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids. A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.
A general solution for the 2-pyridyl problem
Dick, Graham R.,Woerly, Eric M.,Burke, Martin D.
supporting information; experimental part, p. 2667 - 2672 (2012/04/23)
Problem solved: An air-stable 2-pyridyl borane that can effectively couple to a wide range of aryl and heteroaryl halides and pseudohalides has evaded the synthesis community for decades. The discovery that Cu(DEA)2 powerfully enables palladium-mediated cross-couplings with air-stable boronates 1 has finally provided a general solution to this problem. DEA=diethanolamine, DMF=N,N′-dimethylformamide, Tf=trifluoromethanesulfonyl. Copyright
Room-temperature highly efficient Suzuki-Miyaura reactions in water in the presence of Stilbazo
Peng, Yi-Yuan,Liu, Jinbiao,Lei, Xiaoli,Yin, Zenlan
supporting information; experimental part, p. 1072 - 1075 (2010/08/04)
An efficient catalytic system for the ligand-free Suzuki-Miyaura reaction in water at room temperature is disclosed, promoted by Stilbazo (stilbene-4,4′-bis[(1-azo)-3,4-dihydroxybenzene]-2,2′-disulfonic acid diammonium salt). The desired carbon-carbon bond formation proceeded well under mild conditions with high efficiency and good functional group tolerance.
A versatile method for suzuki cross-coupling reactions of nitrogen heterocycles
Kudo, Noriaki,Perseghini, Mauro,Fu, Gregory C.
, p. 1282 - 1284 (2007/10/03)
(Chemical Equation Presented) A wide-ranging study of Suzuki reactions which use nitrogen-containing heterocycles is described (see scheme; dba = dibenzylideneacetone, Cy = cyclohexyl). This method is highly versatile (a single procedure was used for all substrates, including boronate esters and trifluoroborates), compatible with a variety of unprotected functionalities (e.g., NH2-and OH-substituted substrates), and efficient even with unactivated aryl chlorides.
Photocatalyzed [2 + 2 + 2]-cycloaddition of nitriles with acetylene: An effective method for the synthesis of 2-pyridines under mild conditions
Heller, Barbara,Sundermann, Bernd,Buschmann, Helmut,Drexler, Hans-Joachim,You, Jingsong,Holzgrabe, Ulrike,Heller, Eberhard,Oehme, Guenther
, p. 4414 - 4422 (2007/10/03)
The photocatalyzed [2 + 2 + 2]-cycloaddition of nitriles with 2 equiv of acetylene to 2-pyridines can be carried out under mild conditions and represents a valuable extension to common synthetical methods. For the ideal wavelength range (350-500 nm), lamps as well as sunlight can be used. Working at room temperature and in organic solvents such as toluene or hexane as well as in water gives satisfying results in many cases. However, it is also possible to vary the solvent and the reaction temperature of the photocatalyzed synthesis and to choose, with respect to the specific substrate, specific requirements for this particular reaction and general requirements of the method. This simple and selective method derives its potential mainly from the large variety of applicable nitriles. Suitable substrates include (functionalized) aliphatic and aromatic nitriles as well as cyanamides derived from secondary amines.
SYNTHESIS OF 5-ARYLATED INDOLES VIA PALLADIUM-CATALYZED CROSS-COUPLING REACTION OF 5-INDOLYLBORONIC ACID WITH ARYL AND HETEROARYL HALIDES
Yang, Youhua,Martin, Arnold R.
, p. 1395 - 1398 (2007/10/02)
Palladium(0)-catalyzed cross-coupling reaction of 5-indolylboronic acid with various aryl and heteroaryl halides results in regioselective formation of 5-arylated indoles in good yields.
INDOLE DERIVATIVES. 133. SYNTHESIS OF 5-(2-PYRIDYL)INDOLE
Akhvlediani, R. N.,Khazhidze, M. M.,Eraksina, V. N.,Suvorov, N. N.
, p. 1221 - 1225 (2007/10/02)
Starting from 2-(4-nitrophenyl)pyridine, the product of the Gomberg arylation of pyridine, 5-(2-pyridyl)indole was prepared by the Japp-Klingman reaction. 13C NMR indicated an inductively transmitted interaction between the pyridine and indole rings.
