847237-12-1Relevant academic research and scientific papers
One-Pot Asymmetric Oxidative Dearomatization of 2-Substituted Indoles by Merging Transition Metal Catalysis with Organocatalysis to Access C2-Tetrasubstituted Indolin-3-Ones
Zhao, Yong-Long,An, Jian-Xiong,Yang, Fen-Fen,Guan, Xiang,Fu, Xiao-Zhong,Li, Zong-Qin,Wang, Da-Peng,Zhou, Meng,Yang, Yuan-Yong,He, Bin
, p. 1277 - 1285 (2022/03/14)
A one-pot approach for the asymmetric synthesis of C2-tetrasubstituted indolin-3-ones from 2-substituted indoles was developed via merging transition metal catalysis with organocatalysis. This strategy involves two processes, including CuI catalyzed oxidative dearomatization of 2-substituted indoles using O2 as green oxidant, and followed by an proline-promoted asymmetric Mannich reaction with ketones or aldehydes. A series of C2-tetrasubstituted indolin-3-ones were obtained in 35–86% yields, 2:1->20:1 dr and 48–99% ee. Moreover, the synthetic 2-tetrasubstituted indolin-3-ones could be easily transformed into 1H-[1,3] oxazino [3,4-a]indol-5(3H)-ones via a [4+1] cyclization process. In addition, the synthetic compound 3 s show certain antibacterial activity against S. aureus ATCC25923 and multi-drug resistance bacterial strain of S. aureus (20151027077) and its MIC values up to 8 μg/mL and 16 μg/mL, respectively. (Figure presented.).
Iron-catalysed radical cyclization to synthesize germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones
Luo, Yani,Tian, Tian,Nishihara, Yasushi,Lv, Leiyang,Li, Zhiping
, p. 9276 - 9279 (2021/09/20)
A simple and efficient strategy for iron-catalysed cascade radical cyclization was developed, by which an array of germanium-substituted indolo[2,1-a]isoquinolin-6(5H)-ones and indolin-2-ones were obtained in one pot with germanium hydrides as radical precursors. A rapid intramolecular radical trapping mode enabled the selective arylgermylation of alkenes over the prevalent hydrogermylation reaction.
Method for synthesizing 2-substituted indole derivative under catalysis of copper
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Paragraph 0051-0054, (2021/09/11)
The invention relates to a method for synthesizing a 2-substituted indole derivative under the catalysis of copper, which comprises the following step of: reacting by taking copper acetylacetonate (Cu (acac) 2) as a catalyst and taking indole and halogenated hydrocarbon as raw materials to obtain the 2-substituted indole derivative. Compared with the prior art, the method has the advantages that the copper acetylacetonate Cu (acac) 2 which is low in price, easy to obtain and stable in property is used as the catalyst, the method is green and economical, the catalyst is used for catalyzing the indole and halogenated hydrocarbon to react to synthesize the 2-substituted indole derivative, the reaction condition is mild, and the selectivity and yield of the product are high; and the synthesis method is simple and green, the 2-substituted indole derivative is directly constructed by using cheap and easily available raw materials indole and halogenated hydrocarbon, and the 2-substituted indole derivative has good substrate universality and has wide application value in the fields of pharmaceutical chemistry, fine chemical industry and the like.
Aniline-initiated and Br?nsted acid-catalyzed one-pot reaction toward 2-aryl-3-sulfenylindoles by using α-aminocarbonyl compounds and primary amines with RSSR
Chen, De,Cheng, Chaozhihui,Deng, Wei,Guan, Wenjian,Liu, Yuxuan,Luo, Yongyue,Xiang, Jiannan,Zhang, Jiajia
, (2020/12/01)
A highly novel method of direct synthesis of 2-aryl-3-sulfenylindoles in moderate to good yields was developed via one-pot tandem reaction of readily available α-aminocarbonyl compounds and catalytic amount of benzenamines with RSSR.
Acid-catalyzed cleavage of C-C bonds enables atropaldehyde acetals as masked C2 electrophiles for organic synthesis
Chen, Shaomin,Gu, Yanlong,Li, Minghao
, p. 10431 - 10434 (2021/10/12)
Acid-catalyzed tandem reactions of atropaldehyde acetals were established for the synthesis of three important molecules, 2,2-disubstituted indolin-3-ones, naphthofurans and stilbenes. The synthesis was realized using novel reaction cascades, which involved the same two initial steps: (i) SN2′ substitution, in which the atropaldehyde acted as an electrophile; and (ii) oxidative cleavage of the carbon-carbon bond of the generated phenylacetaldehyde-type products. Compared with literature methods, the present protocol not only avoided the use of expensive noble metal catalysts, but also enabled a simple operation.
An iron(iii)-catalyzed dehydrogenative cross-coupling reaction of indoles with benzylamines to prepare 3-aminoindole derivatives
Chen, Wei-Li,Li, Kun,Liang, Cui,Liang, Wang-Fu,Liao, Wei-Cong,Mo, Dong-Liang,Qiu, Pei-Wen,Su, Gui-Fa
, p. 9610 - 9616 (2021/12/09)
We report a green cascade approach to prepare a variety of 3-aminoindole derivatives in good to excellent yields through an iron(iii)-catalyzed dehydrogenative cross-coupling reaction of 2-arylindoles and primary benzylamines under mild reaction conditions. Mechanistic studies show that a cascade reaction involves a tert-butyl nitrite (TBN)-mediated nitrosation of 2-substituted indoles and a 1,5-hydrogen shift to afford indolenine oximes, sequential iron(iii)-catalyzed condensation and a 1,5-hydrogen shift over four steps in a one-pot reaction. The reaction shows a broad substrate scope of indoles and benzylamines and tolerates a wide range of functional groups. Moreover, the reaction is easily performed at the gram scale without producing waste after the reaction is completed. The 3-aminoindole product is purified by simple extraction, washing, and recrystallization without flash column chromatography. A double imine ligand containing the 3-aminoindole unit is facile to obtain in a 52% yield in one step. The present method highlights readily available starting materials, a simple purification procedure, and the usage of cheap, nontoxic, and environmentally benign iron(iii) catalysts. This journal is
Discovery of New 4-Indolyl Quinazoline Derivatives as Highly Potent and Orally Bioavailable P-Glycoprotein Inhibitors
Chen, Zhe-Sheng,Dai, Qing-Qing,Li, Guo-Bo,Liu, Hong-Min,Liu, Hui,Wang, Bo,Wang, Shaomeng,Yu, Bin,Yuan, Shuo,Zhang, Jing-Ya,Zhang, Xiao-Nan,Zuo, Jia-Hui
, p. 14895 - 14911 (2021/10/12)
The major drawbacks of P-glycoprotein (P-gp) inhibitors at the clinical stage make the development of new P-gp inhibitors challenging and desirable. In this study, we reported our structure-activity relationship studies of 4-indolyl quinazoline, which led to the discovery of a highly effective and orally active P-gp inhibitor, YS-370. YS-370 effectively reversed multidrug resistance (MDR) to paclitaxel and colchicine in SW620/AD300 and HEK293T-ABCB1 cells. YS-370 bound directly to P-gp, did not alter expression or subcellular localization of P-gp in SW620/AD300 cells, but increased the intracellular accumulation of paclitaxel. Furthermore, YS-370 stimulated the P-gp ATPase activity and had moderate inhibition against CYP3A4. Significantly, oral administration of YS-370 in combination with paclitaxel achieved much stronger antitumor activity in a xenograft model bearing SW620/Ad300 cells than either drug alone. Taken together, our data demonstrate that YS-370 is a promising P-gp inhibitor capable of overcoming MDR and represents a unique scaffold for the development of new P-gp inhibitors.
Chiral Br?nsted Acid from Chiral Phosphoric Acid Boron Complex and Water: Asymmetric Reduction of Indoles
Yang, Kai,Lou, Yixian,Wang, Chenglan,Qi, Liang-Wen,Fang, Tongchang,Zhang, Feng,Xu, Hetao,Zhou, Lu,Li, Wangyang,Zhang, Guan,Yu, Peiyuan,Song, Qiuling
, p. 3294 - 3299 (2020/01/21)
A new chiral Br?nsted acid, generated in situ from a chiral phosphoric acid boron (CPAB) complex and water, was successfully applied to asymmetric indole reduction. This “designer acid catalyst”, which is more acidic than TsOH as suggested by DFT calculations, allows the unprecedented direct asymmetric reduction of C2-aryl-substituted N-unprotected indoles and features good to excellent enantioselectivities with broad functional group tolerance. DFT calculations and mechanistic experiments indicates that this reaction undergoes C3-protonation and hydride-transfer processes. Besides, bulky C2-alkyl-substituted N-unprotected indoles are also suitable for this system.
Merging Visible Light Photocatalysis and l-/d-Proline Catalysis: Direct Asymmetric Oxidative Dearomatization of 2-Arylindoles to Access C2-Quaternary Indolin-3-ones
Dong, Chun-Lin,Ding, Xuan,Huang, Lan-Qian,He, Yan-Hong,Guan, Zhi
supporting information, p. 1076 - 1080 (2020/02/15)
A mild and effective method for asymmetric synthesis of C2-quaternary indolin-3-ones directly from 2-arylindoles by combining visible light photocatalysis and organocatalysis is described. In this reaction, 2-substituted indoles undergo photocatalyzed oxidative dearomatization, followed by an organocatalyzed asymmetric Mannich reaction with ketones or aldehydes. Products with opposite configurations are easily obtained in satisfactory yields with excellent enantio- A nd diastereoselectivity by employing readily available l- A nd d-proline as chiral organocatalysts.
Highly enantioselective electrosynthesis of C2-quaternary indolin-3-ones
Chen, Yu-Jue,Chen, Yuan,Ding, Xuan,Guan, Zhi,He, Yan-Hong,Lu, Fo-Yun
supporting information, p. 623 - 626 (2020/01/28)
A highly enantioselective and direct synthesis of C2-quaternary indolin-3-ones from 2-arylindoles by combining electrochemistry and organocatalysis is described. Excellent enantioselectivities (up to 99% ee) and diastereoselectivities (>20 : 1) can be obtained through anodic oxidation in combination with asymmetric proline-catalyzed alkylation in an undivided cell under constant-current conditions.
