34897-84-2Relevant articles and documents
Construction of a benzo[b]azepine skeleton through decarboxylative ylide [6+1] annulations with modified vinyl benzoxazinanones
Li, Qing-Zhu,Jia, Zhi-Qiang,Chen, Lin,Zhang, Xiang,Leng, Hai-Jun,Zeng, Rong,Liu, Yan-Qing,Zou, Wen-Lin,Li, Jun-Long
supporting information, p. 814 - 818 (2021/02/16)
A Lewis acid-promoted [6+1] annulation between sulfur ylides and modified vinyl benzoxazinanones was described. In this reaction, the newly designed vinyl benzoxazinanones could serve as a novel six-atom synthon, and the key to success is the installation of an electron-withdrawing group on the alkene moiety of the benzoxazinanones. A broad range of substrates are compatible with this mild reaction system, thereby providing a facile and practical approach for constructing a benzo[b]azepine skeleton.
Access to 5,6-Spirocycles Bearing Three Contiguous Stereocenters via Pd-Catalyzed Stereoselective [4 + 2] Cycloaddition of Azadienes
Fairuz Binte Sheikh Ismail, Siti Nur,Yang, Binmiao,Zhao, Yu
supporting information, p. 2884 - 2889 (2021/05/05)
We present herein a highly diastereo- and enantioselective Pd-catalyzed [4 + 2] cycloaddition of benzofuran-derived azadienes with vinyl benzoxazinanones, which represents a rare highly stereoselective cycloaddition of this class of fused azadienes as a two-atom synthon. The use of a phosphoramidite ligand bearing a chiral secondary amine with a simple biphenyl backbone proved to be the key to construct the novel spirocyclic tetrahydroquinoline scaffold containing three contiguous stereocenters as a single diastereomer in high enantioselectivity.
Metal-Free C-C/C-N/C-C Bond Formation Cascade for the Synthesis of (Trifluoromethyl)sulfonylated Cyclopenta[ b]indolines
Lázaro-Milla, Carlos,Yanai, Hikaru,Almendros, Pedro
supporting information, p. 2921 - 2926 (2021/05/05)
A bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] inserted into a sequential cyclization cascade resulted in the direct formation of gem-bis(triflyl)ated cyclopenta[b]indolines from anilide-derived allenols and alkenols. This catalyst- and irradiation-free sequence facilitated the efficient preparation of functionalized tricyclic indoline cores bearing two contiguous stereocenters. The formed cyclopenta[b]indolines can be easily transformed into a wide variety of triflylated indolines, including the tetracycle ring system found in polyveoline.
A Convenient Formal [4+2] Heterocylization Route to Bis(triflyl)tetrahydroquinolines
Lázaro-Milla, Carlos,Almendros, Pedro
supporting information, p. 13534 - 13538 (2021/08/13)
We report the sustainable and efficient synthesis of a new type of quinoline derivatives bearing one or two SO2CF3 groups. The protocol is metal-, catalyst- and irradiation-free, involves the use of readily available and stable precursors, and avoids the formation of side products. Also, the mild conditions of the process allow the tolerance of a wide range of functional groups.
Preparation and Application of α-Imino Ketones through One-Pot Tandem Reactions Based on Heyns Rearrangement
Li, Ling,Zhang, Shiqi,Deng, Xiongfei,Li, Guangxun,Tang, Zhuo,Zhao, Gang
supporting information, p. 6819 - 6824 (2021/09/08)
α-Imino ketone is a useful building block for the preparation of α-amino ketones and α-amino alcohols. However, its preparation has been seldomly seen. Herein, a metal-free and operationally simple strategy has been developed to generate α-imino ketones with high regioselectivity. Meanwhile, the method allowed for the preparation of various N,O-ketals with high regioselectivities and diastereoselectivities through cascade reactions in one pot.
Visible-light-induced radical isocyanide insertion protocol for the synthesis of difluoromethylated spiro[indole-3,3′-quinoline] derivatives
Zhang, Jingjing,Xu, Wentao,Qu, Yi,Liu, Yuxiu,Li, Yongqiang,Song, Hongjian,Wang, Qingmin
supporting information, p. 15212 - 15215 (2020/12/21)
Herein, we report the first protocol for visible-light-induced radical isocyanide insertion reactions between 3-(2-isocyanobenzyl)-indoles and bromodifluoroacetates or bromodifluoroacetamides. The protocol, which has good functional group tolerance and a broad substrate scope, constitutes an efficient and general route to difluoromethylated spiro[indole-3,3′-quinoline] derivatives. This journal is
Red phosphorescent compounds and organic electroluminescence device prepared by using compounds
-
Paragraph 0055-0057, (2020/02/19)
The invention discloses red phosphorescent compounds and an organic electroluminescence device prepared by using the compounds. In the organic electroluminescence device including an anode, a hole injection layer, a hole transport layer, a light emitting
One-pot synthesis of 2-hydroxymethylindoles: via photoredox-catalyzed ketyl-ynamide coupling/1,3-allylic alcohol transposition
Chen, Yang-Bo,Wang, Kun,Wang, Ze-Shu,Xu, Zhou,Ye, Long-Wu
supporting information, p. 4483 - 4488 (2020/08/10)
An efficient visible-light-mediated ketyl-ynamide coupling by employing ynamides bearing alkyl sulfonyl substituents to deliver eneindolin-3-ols has been developed. Subsequent 1,3-transposition of allylic alcohols in one pot is capable of synthesizing 2-hydroxymethylindoles in generally moderate to good yields. The synthetic utility of this protocol has also been demonstrated by the facile and practical synthesis of two bioactive molecules. The use of readily available substrates, a simple procedure and benign reaction conditions render this method a viable alternative for the synthesis of 2-hydroxymethylindoles. This journal is
Sequential Phosphine-Catalyzed [4 + 2] Annulation of β′-Acetoxy Allenoates: Enantioselective Synthesis of 3-Ethynyl-Substituted Tetrahydroquinolines
Zhang, Qinglong,Jin, Hongxing,Feng, Jiaxu,Zhu, Yannan,Jia, Penghao,Wu, Chengzhou,Huang, You
supporting information, p. 1407 - 1411 (2019/03/07)
The first enantioselective sequential phosphine-catalyzed (SPC as abbreviation) mode for the formation of tetrahydroquinolines with an ethynyl-substituted all-carbon quaternary stereogenic center is reported. In this SPC process, a novel [4 + 2] annulation process was devised employing α-substituted allenoates as C2 synthons (α-β′, 1,2-dipole) for the first time. 3-Ethynyl-substituted tetrahydroquinolines were readily prepared in good yields and high enantioselectivities.
Benzoazepine-Fused Isoindolines via Intramolecular (3 + 2)-Cycloadditions of Azomethine Ylides with Dinitroarenes
Wales, Steven M.,Rivinoja, Daniel J.,Gardiner, Michael G.,Bird, Melissa J.,Meyer, Adam G.,Ryan, John H.,Hyland, Christopher J. T.
supporting information, p. 4703 - 4708 (2019/06/27)
Aminobenzaldehydes bearing a pendant 3,5-dinitrophenyl group react thermally with N-substituted α-amino acids to form unprecedented benzoazepine-fused isoindolines. The reaction proceeds via a dearomatization/rearomatization sequence involving an intramolecular (3 + 2)-cycloaddition between the in situ formed azomethine ylide and the dinitroarene. Various glycine derivatives are tolerated as well as branched substrates based on cyclic, α-mono-, and α,α-disubstituted amino acids, giving single diastereomers in many cases. The method is scalable and gives products with a nitro group ready for further manipulation.
