- Transition-metal-free insertion of benzyl bromides into 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde: One-pot switchable syntheses of benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones and 3-arylquinolin-4-ones mediated by base
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A transition-metal-free insertion of benzyl group between aldehyde and imidazole of 2-(1H-benzo[d]imidazol-1-yl)benzaldehyde was achieved for the first time. Two diverse sets of quinolin-4-one derivatives: benzo[4,5]imidazo[1,2-a]quinolin-5(7H)-ones (2) and 3-arylquinolin-4-ones (3) were synthesized based on identical starting materials 2-(1H-benzo[d]imidazol-1-yl)benzaldehydes (1) and benzyl bromides. In the preparations, two key intermediates I and II were involved and might be synthesized in situ through the reaction of an intra-Breslow intermediate with benzyl bromide via an enol attack in the presence of base or a NHC-based enamine attack in the absence of base, respectively, in which the intra-Breslow intermediate might function as a nucleophilic reagent by following two novel different pathways.
- Xu, Huayan,Xu, Liang,Luo, Xiaowei,Wang, Junfeng,Zhou, Xuefeng,Yang, Bin,Li, Ding,Luo, Zaigang,Liu, Yonghong,Liao, Shengrong
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p. 2785 - 2796
(2019/04/13)
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- Palladium(II) 9,10-phenanthrenequinone N-substituted thiosemicarbazone/semicarbazone complexes as efficient catalysts for N-arylation of imidazole
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A series of palladium complexes, [PdCl(L1-4)] (1-4) (L1 = 9,10-phenanthrenequinone thiosemicarbazone, L2 = 9,10-phenanthrenequinone methylthiosemicarbazone, L3 = 9,10-phenanthrenequinone phenylthiosemicarbazone, and L4 = 9,10-phenanthrenequinone semicarbazone), have been synthesized and characterized by elemental analyses, UV-vis, FT-IR, 1H and 13C NMR, and ESI-Mass spectroscopic methods. The catalytic efficiency of the synthesized complexes was examined against N-arylation of imidazole. The system works well with the electron-rich, -neutral, and -deficient aryl halides to afford the products in good to excellent yields. Sterically congested aryl halides and heteroaryl halides have also been used as substrates to provide N-arylated heterocycles. In addition, this methodology can be applicable to other substrates with N-containing heterocycles.
- Anitha, Panneerselvam,Manikandan, Rajendran,Viswanathamurthi, Periasamy
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p. 3537 - 3550
(2015/09/28)
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- Magnetically retrievable lepidocrocite supported copper oxide nanocatalyst (Fe-CuO) for N-arylation of imidazole
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A simple and efficient lepidocrocite-supported copper oxide catalyst (Fe-CuO) has been successfully prepared by a simple precipitation method in aqueous medium from readily available inexpensive starting materials and was used as a heterogeneous nanocatal
- Sivakami,Babu, S. Ganesh,Dhanuskodi,Karvembu
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p. 8571 - 8578
(2015/03/03)
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- Regioselective synthesis of diversely substituted diazoninones through a post-Ugi gold-catalyzed intramolecular hydroarylation process
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A highly efficient approach for the regioselective construction of fused nine-membered rings (diazoninone framework) was developed by employing sequential Ugi and gold-catalyzed intramolecular hydroarylation reactions. The scope of this intramolecular cyc
- Li, Zhenghua,Kumar, Amit,Vachhani, Dipak D.,Sharma, Sunil K.,Parmar, Virinder S.,Van Der Eycken, Erik V.
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p. 2084 - 2091
(2014/04/17)
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- Silver(I)-promoted intramolecular addition of N-heterocyclic carbenes towards unsaturated esters in water
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Silver(I)-promoted intramolecular addition reaction between N-heterocyclic carbene and unsaturated esters in water is described. The reaction leads to 1H-imidazo[1,2-a]indole derivatives in moderate to excellent yields.
- Shang, Xiaobo,Chen, Chao,Qiu, Huayu,Chen, Wanzhi
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p. 3073 - 3077
(2014/04/17)
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- Ultrafast singlet - singlet energy transfer in self-assembled via metal - ligand axial coordination of free-base porphyrin - zinc phthalocyanine and free-base porphyrin - zinc naphthalocyanine Dyads
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Singlet - singlet energy transfer in self-assembled via axial coordination of imidazole-appended (at different positions of one of the meso-phenyl entities) free-base tetraphenylporphyrin, H2PIm, to either zinc phthalocyanine, ZnPc, or zinc nap
- Maligaspe, Eranda,Kumpulainen, Tatu,Lemmetyinen, Helge,Tkachenko, Nikolai V.,Subbaiyan, Navaneetha K.,Zandler, Melvin E.,D'Souza, Francis
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experimental part
p. 268 - 277
(2010/05/11)
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- CuI nanoparticles for C-N and C-O cross coupling of heterocyclic amines and phenols with chlorobenzenes
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(Chemical Equation Presented) Employing CuI nanoparticles as an efficient catalyst for the cross-coupling reactions of various N/O nucleophilic reagents with aryl chlorides could be successfully carried out under mild conditions in the absence of both the ligands and strong bases. A variety of products including N-arylimidazoles and aryl ethers were synthesized in good to excellent yields. 2009 American Chemical Society.
- Sreedhar,Arundhathi,Reddy, P. Linga,Kantam, M. Lakshmi
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supporting information; experimental part
p. 7951 - 7954
(2010/01/16)
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- 1,2,3,4-Tetrahydro-8-hydroxyquinoline-promoted copper-catalyzed coupling of nitrogen nucleophiles and aryl bromides
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(Chemical Equation Presented) Based on the dramatic accelerating effect of 2-aminophenol, three ligands derived from 2-aminophenol were developed. Copper-catalyzed coupling reaction of nitrogen-containing nucleophiles with aryl bromides was efficiently carried out under mild conditions using 1,2,3,4-tetrahydro-8-hydroxyquinoline as a novel, simple, and versatile ligand.
- Wang, Huifeng,Li, Yaming,Sun, Fangfang,Feng, Yang,Jin, Kun,Wang, Xiuna
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supporting information; experimental part
p. 8639 - 8642
(2009/04/04)
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- Imidazol-1-yl and Pyridin-3-yl Derivatives of 4-Phenyl-1,4-dihydropyridines Combining Ca2+ Antagonism and Thromboxane A2 Synthase Inhibition
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A series of derivatives of 4-phenyl-1,4-dihydropyridine bearing imidazol-1-yl or pyridin-3-yl moieties on the phenyl ring were synthesized with the aim of combining Ca2+ antagonism and thromboxane A2 (Tx A2) synthase inhib
- Cozzi, Paolo,Carganico, Germano,Fusar, Domenico,Grossoni, Mauro,Menichincheri, Maria,et al.
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p. 2964 - 2972
(2007/10/02)
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