891-32-7Relevant academic research and scientific papers
Metal-Free Synthesis of Benzo[a]phenanthridines from Aromatic Aldehydes, Cyclohexanones, and Aromatic Amines
Chen, Shanping,Deng, Guo-Jun,Jiang, Pingyu,Jiang, Shuxin,Shan, Zhifei,Wang, Quanyuan,Zheng, Haolin
supporting information, p. 365 - 370 (2021/12/27)
A three-component synthesis of benzo[α]phenanthridines from aromatic aldehydes, cyclohexanones, and aromatic amines has been developed, which is mediated by KI/DMSO/camphorsulfonic acid to afford a variety of functionalized benzo[α]phenanthridines in satisfactory yields. The present strategy provides a biaryl motif ortho to the nitrogen atom which has the potential to be used as ligand by further modification. With the advantages of readily available starting materials, transition-metal-free conditions, gram-scale synthesis, and broad substrate scope, this three-component protocol provides an efficient approach for the preparation of diverse benzo[α]phenanthridines.
Copper-Catalyzed Intramolecular Amination of C(sp3)-H Bond of Secondary Amines to Access Azacycles
Jin, Ruo-Xing,Dai, Jing-Cheng,Li, Yan,Wang, Xi-Sheng
supporting information, p. 421 - 426 (2021/01/26)
The cross-coupling of C-N bond directly from inert C-H bonds is an ideal approach to synthesize saturated azacycles due to its high efficiency and atom economy. In this article, a copper-catalyzed intramolecular amination via the cross coupling of C(sp3)-H and N-H bonds of secondary amine has been reported, which exhibit excellent chemo- and regioselectivity, extensive substrate scope, and functional group tolerance in good to excellent yield, offering an efficient pathway to build nitrogen-containing heterocycle skeletons.
Rhodium catalyzed multicomponent dehydrogenative annulation: one-step construction of isoindole derivatives
Cheng, Biao,Lyu, Hairong,Quan, Yangjian,Xie, Zuowei
supporting information, p. 7930 - 7933 (2021/08/17)
A strategy for one-pot synthesis of isoindoles is describedviaa catalytic multicomponent dehydrogenative annulation of diarylimines, vinyl ketones and simple amines. In the presence of a rhodium catalyst and Cu oxidant, four C-H and two N-H bonds are activated along with the formation of one new C-C and two new C-N bonds, leading to a series of isoindole derivatives in good to very high isolated yields.
Rhodium-Catalyzed Dehydrogenative Annulation of N-Arylmethanimines with Vinylene Carbonate for Synthesizing Quinolines
Hu, Yan,Nan, Jiang,Yin, Jiacheng,Huang, Guanjie,Ren, Xin,Ma, Yangmin
supporting information, p. 8527 - 8532 (2021/11/13)
Here we report a novel Rh-catalyzed C-H/C-H alkenylation of N-arylmethanimines with vinylene carbonate acting as a vinylene unit. Forty examples of C3,C4-nonsubstituted quinolines were achieved from commercially available starting materials. This identified process features an exceedingly simple system, a lower loading of catalyst, and the capacity for postfunctionalization with bioactive molecules.
Switchable Imine and Amine Synthesis Catalyzed by a Well-Defined Cobalt Complex
Paudel, Keshav,Xu, Shi,Hietsoi, Oleksandr,Pandey, Bedraj,Onuh, Chuka,Ding, Keying
supporting information, p. 418 - 426 (2021/02/01)
Switchable imine and amine synthesis catalyzed by a tripodal ligand-supported well-defined cobalt complex is presented herein. A large variety of primary alcohols and amines were selectively converted to imines or amines in good to excellent yields. It is discovered that the base plays a crucial role on the selectivity. A catalytic amount of base leads to the imine formation, while an excess loading of base results in the amine product. This strategy on product selectivity also strongly depends on the organometallic catalysts in use. We expect that the present study could provide useful insights toward selective organic synthesis and catalyst design.
Novel androgen receptor antagonist identified by structure-based virtual screening, structural optimization, and biological evaluation
Chai, Xin,Fu, Weitao,Hou, Tingjun,Li, Dan,Pang, Jinping,Shan, Lvhu,Sheng, Rong,Tang, Qin,Wang, Ercheng,Wang, Xuwen,Xu, Lei,Xu, Xiaohong,Zhang, Minkui
, (2020/02/29)
Androgen receptor (AR) plays important roles in the development of prostate cancer (PCa), and therefore it has been regarded as the most important therapeutic target for both hormone-sensitive prostate cancer (HSPC) and advanced PCa. In this study, a nove
Thiazoline-Iridium (III) Complexes and Immobilized Nanomaterials as Selective Catalysts in N-Alkylation of Amines with Alcohols
Denizalt?, Serpil,Dayan, Serkan,Günnaz, Salih,?ahin, Ertan
, (2020/10/02)
In this research, a new series of thiazoline-iridium (III) complexes (4–7) derived from cysteine were prepared and fully characterized by conventional methods. The molecular structure of complex 5 was also determined by single-crystal X-ray diffraction. These complexes were evaluated as catalysts for hydrogen-borrowing reactions of amines with alcohols. In particular, complex 5 showed the best activity as catalyst. Various amines have been alkylated with alcohols affording moderate to good yield (33–99%). Moreover, the immobilized nanomaterials (M1,2) were fabricated by sonication process from the best catalyst 5 with the multi-walled carbon nanotubes (MWCNTs) and graphene oxide (GO), respectively, and characterized by X-ray diffraction (XRD), Fourier transform infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM), energy dispersive X-ray (EDX) spectroscopy, and inductively coupled plasma-mass spectrometry (ICP-MS). The M1,2 nanomaterials were also tested as catalysts in model catalytic reaction for N-alkylation. The M1 nanomaterial showed significantly higher activity than the M2 nanomaterial. The M1 catalyst was recovered by filtration and reused for four catalytic cycles with high conversion (99%, 97%, 96%, and 86%).
Central-to-Axial Chirality Conversion Approach Designed on Organocatalytic Enantioselective Povarov Cycloadditions: First Access to Configurationally Stable Indole–Quinoline Atropisomers
Bisag, Giorgiana Denisa,Pecorari, Daniel,Mazzanti, Andrea,Bernardi, Luca,Fochi, Mariafrancesca,Bencivenni, Giorgio,Bertuzzi, Giulio,Corti, Vasco
supporting information, p. 15694 - 15701 (2019/11/28)
The first stereoselective synthesis of enantioenriched axially chiral indole–quinoline systems is presented. The strategy takes advantage of an organocatalytic enantioselective Povarov cycloaddition of 3-alkenylindoles and N-arylimines, followed by an oxi
Double C-S bond formation: Via C-H bond functionalization: Synthesis of benzothiazoles and naphtho[2,1- d] thiazoles from N -substituted arylamines and elemental sulfur
Zhu, Xiaoming,Yang, Yuzhong,Xiao, Genhua,Song, Jianxin,Liang, Yun,Deng, Guobo
, p. 11917 - 11920 (2017/11/06)
A novel, atom economic, and environmentally friendly method for the synthesis of 2-substituted benzothiazoles and 2-substituted naphtho[2,1-d]thiazoles from N-substituted arylamines and elemental sulfur has been developed under metal-free conditions. The reaction underwent the process of double C-S bond formation through C-H bond functionalization.
Method for preparing imine compound from alcohol and amine through catalytic oxidation
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Paragraph 0050, (2017/08/31)
The invention discloses a method for preparing an imine compound from alcohol and amine through catalytic oxidation. According to the method, an alcohol compound and an amine compound are used as reaction substrates, and a feeding mol ratio of the alcohol compound to the amine compound is 100: 100-60; 9-azabicyclo[3.3.1]nonane N-oxyl free radical is used as a catalyst, potassium hydroxide is used as an auxiliary agent, and a feeding mol ratio of the amine compound to the 9-azabicyclo[3.3.1]nonane N-oxyl free radical to potassium hydroxide is 100: 1-6: 10-50; air is used as an oxidizing agent, the reaction substrates are added into an organic solvent, and the mass of the used organic solvent is 2.5 to 5 times of the reaction substrate the amine compound; and a reaction is carried out at normal pressure at a temperature of 70 to 110 DEG C for 2 to 12 h, and aftertreatment is carried out after completion of the reaction so as to obtain the imine compound. The method provided by the invention is simple and safe to operate, reduces environmental cost due to usage of clean oxygen as the oxidizing agent and prevents the problem of transition-metal pollution by discarding usage of any transition-metal catalyst.
